The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to for more information on the podcast, show notes, resources and more.
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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch










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Now displaying: Category: Investing
Feb 3, 2023

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor’s product vision and user experience, managing a 70-person product and design org. 

Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe’s first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter.

David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos.

Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay.

Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products. 

Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and one of the most popular newsletters on Substack. 

For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015.

Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe’s Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012.

In Today's Episode on How to Hire a Product Manager, We Discuss:

1.) When to Hire Your First PM:

  • What are the core signs that the founder must delegate and hire their first PM?
  • What are the first things that are breaking when you do not have one but need one?
  • How does the timing of the first PM differ when comparing B2B vs B2C?

2.) What is the Right Profile:

  • What should founders look for in this first PM hire? What traits make the best?
  • What are the biggest red flags in the personalities and styles of potential candidates?
    • Should they have experience in the product domain they are entering?
  • What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume?

3.) The Hiring Process: How To Hire a Product Manager

  • How do we structure and run the hiring process for this person?
  • What tests can we do to understand if they have the skill set we need for the role?
  • How do we structure a hiring panel to make this process more effective?
  • What are the biggest mistakes founders make in the hiring process for PMs?

Feb 1, 2023

Alex Bouaziz is the Co-Founder and CEO @ Deel, the all-in-one platform made to simplify all things HR, built for global teams near and far. In the last year alone, Alex has scaled Deel from $57M in ARR to $295M, EBITDA positive since Sept 2022, 85%+ gross margins, and over $5BN paid out to 250,000 people. Alex has raised over $679M with Deel, pricing the company at the last round at $12.1BN. Investors in the company include a16z, Spark Capital, Coatue, and many more.

In Today's Episode with Alex Bouaziz We Discuss:

1.) From Student in London to Decacorn Founder:

  • How Alex made his way into the world of startups and how he came up with the idea for Deel?
  • Did Alex always know he would be successful when he was growing up?
  • What does Alex know now that he wishes he had known when he was starting?

2.) The Importance of Execution:

  • How important does Alex think speed of execution is for startups?
  • What can startups do to deliberately increase their speed of execution?
  • How does Alex think about the dilemma of losing quality with speed?
  • What does Alex think you do need to go slow on to ensure it is perfect?
  • How does Alex think about focus and prioritisation today with Deel?

3.) Scaling to $295M in ARR in 3 Years:

  • When did Alex know he had true product-market fit with Deel?
  • How did Alex use a 50-person Whatsapp group to both determine product market fit and to navigate product direction for the company?
  • What was the key to Deel's blitz scaling strategy? What worked? What did not work?
  • How did Alex hire 2,000 people in such a short space of time?
  • What broke first in the organisation? How could they have prevented it?

4.) Secondaries, Angel Investing and Wealth Management:

  • How much did Alex take out in secondaries in the last round of funding?
  • How did Alex determine how much cash to allocate to angel investing?
  • Why does Alex believe most founders make poor angel investments when they have cash?
  • What have been Alex's biggest lessons from investing? How has it changed how he operates?
  • Why should all founders be super transparent in investor updates?

Jan 30, 2023

Hunter Walk and Satya Patel are Co-Founders and Partners @ Homebrew, one of the leading seed funds of the last decade. Following 10 years of stellar returns with investments in the likes of Chime, Plaid, Gusto and many others, they decided to not accept any further LP capital and to only invest their own money moving forward through Homebrew Forever.

In Today's Discussion on Homebrew We Breakdown:

1. ) The Foundings of a Great Partnership:

  • What was the moment when Hunter and Satya decided they were going to go out and raise their first fund with Homebrew I?
  • What are the core principles that all founding partners need to align on before they start a firm together? What questions should they ask of each other?
  • Why does being independently wealthy coming into a partnership make the partnership easier and more efficient to operate? What changes when the partners have money already?

2.) What Changes When Moving From LP Dollars to Personal Capital:

  • Why did Hunter and Satya decide to not raise any further capital from external LPs?
  • Asset allocation-wise, how did they determine how much is the right amount to set aside for the first 2 years of investing? How many investments do they want to make with that cash?
  • How does investing their personal capital change their deployment pace and cadence?
  • How does it change their approach to reserves management and follow-on financing?
  • How does it change their approach to pricing? How price sensitive are they today?

3.) Analyzing the Seed Landscape Today:

  • Why do Hunter and Satya not think that a $100M seed fund is enough to properly execute a world-class seed strategy today?
  • Who is their competition with the new strategy? How does it change their relationship with large multi-stage funds? How does it change their relationship with seed funds?
  • Do they agree that the last generation of sub $20M micro-funds will not raise another fund in this cycle? How did their entrance impact the seed landscape over the last few years?
  • Why are LPs also to blame for many of the original seed managers raising larger and larger funds?

4.) Companies: Money and People are The Problem:

  • Why has too much money been such a problem for many Homebrew portfolio companies over the last few years? How has too much money changed their execution plans?
  • What happens to the "living dead" companies with many years of runway but no product market fit?
  • Who does this market cater to well? Who will thrive in this market?
  • What have people forgotten about both startups and venture in the last 2 years that we have to remember?
  • Why is this generation so entitled and expectant? Why are startups not a get-rich-quick scheme?

Jan 27, 2023

Cliff Obrecht is the Co-Founder & COO @ Canva, the free-to-use online graphic design tool that makes it easy for anyone to design anything from presentations to videos and social media. Cliff and Mel have scaled Canva to over 60 million monthly users, 2,000 employees, and 500,000 teams from companies like Intel and Zoom using Canva. During this incredible growth journey, they have raised over $580M with their last round valuing the company at over $40BN.

In Today's Episode with Cliff Obrecht

1.) From Teacher to Billionaire Tech Founder:

  • How did Keith make his way into the world of tech with his founding of FusionBooks? What did the process with FusionBooks teach him about how to run Canva?
  • How did the early fundraising days for Canva go? Why does Cliff think they got over 100 no's?
  • What are Cliff's biggest pieces of advice for founders today, not in Silicon Valley, looking to raise from Silicon Valley VCs?

2.) Scaling to $40BN: The Biggest Lessons:

  • What does Cliff mean when he says the secret to successful hiring is looking for "distance traveled"? How does he determine this in the interview process?
  • What have been some of the single biggest lessons in what it takes to acquire the best talent?
  • What are some of the biggest mistakes Cliff has made in talent acquisition? How has his process changed as a result?
  • What do Canva do to get the best operators as advisors in the company? How do they compensate these advisors? What does Cliff advise founders on how to do the same?

3.) The Art of Deal-Making:

  • How does Cliff think through what makes a "good deal"? How does he approach negotiation?
  • What are the biggest mistakes founders make when negotiating and doing deals?
  • What have been Cliff's biggest lessons on successful investor relations over the years?
  • How does Cliff and Canva approach acquisitions? What do they look for? What is their process? Why do most tech companies approach acquisitions the wrong way?

4.) Cliff Obrecht: Money, Fatherhood and Marriage:

  • How does Cliff analyze his relationship to money today? How much money is enough? How has his relationship to money changed over time?
  • Why have Cliff and Mel given away over $10BN to their foundation? Why is philanthropy so hard to do effectively?
  • Why would Cliff hate for his children to be brought up in excess wealth?
  • What does "great fatherhood" mean to Cliff? What are the most challenging aspects of parenting?
  • What are the secrets to a happy marriage? How does co-founding a company with your other half work well? How does it work poorly?

Jan 25, 2023

Stevie Case is the CRO @ Vanta where she oversees Vanta’s go-to-market team to support the company’s rapid growth. Prior to joining Vanta, Stevie was Vice President of Mid-Market Sales at Twilio, joining as one of their first account executives, Stevie helped to grow the sales team from a dozen to over 1,000 team members and played a pivotal role in establishing Twilio’s enterprise business with key Fortune 500 customers, generating more than $400 million in annual recurring revenue. If that was not enough, Stevie is also a Founding Operator @ Coalition Network and a prominent angel investor.

In Today's Episode with Stevie Case We Discuss:

1. ) From World's First Pro Female Gamer to CRO:

  • How did Stevie make her way from pro gamer to CRO? How did her career in gaming make her a better CRO and sales leader?
  • In her early sales career, how did being a single mother with a child impact her approach to sales?
  • What can founders do to make workplaces more inclusive for parents today?

2.) Enterprise or PLG: Which One To Choose:

  • Why does Stevie believe it is not right to do both PLG and enterprise at the same time for startups?
  • How can startups and sales teams move into enterprise selling gradually through testing and without committing a significant budget to an enterprise sales team?
  • How do founders know when is the right time to move from PLG to enterprise? What are the signs?

3.) The Mythical Sales Playbook:

  • How does Stevie define the term "sales playbook" today? What is it not?
  • Should the founder be the person to create the sales playbook? If not them, then who?
  • When is the right time to make your first sales hire? When is the wrong time?

4.) Mastering the Hiring Process in Sales Recruits:

  • How should we structure the interview process for new sales reps?
  • What is the right profile for these first sales hires?
  • How do the best sales talent answer questions and perform in interview processes?
  • How can we really test for grit and curiosity in the interview process?
  • What are the single biggest mistakes founders make when hiring for sales?

5.) Discovery, Discounting, Deal Velocity:

  • With sales cycles being so long, how do you know if enterprise sales reps are good?
  • What is the difference between good discovery vs bad discovery?
  • Should founders engage in discounting to get deals over the line? When does it work?

Jan 23, 2023

Albert Wenger is a managing partner at Union Square Ventures, one of the most successful venture firms of the last decade with a portfolio including Coinbase, Twitter, Twilio, Etsy, and many more. Before joining USV, Albert was the president of through the company’s sale to Yahoo and an angel investor (Etsy, Tumblr). He previously founded or co-founded several companies, including a management consulting firm and an early-hosted data analytics company.

In Today's Episode with Albert Wenger We Discuss:

1.) From Failed Startup Founder to Leading VC:

  • How Albert transitioned from being a failed entrepreneur to being one of the most respected venture investors with USV today?
  • What were the clear signs for Albert that he was not a good entrepreneur?
  • Why does Albert believe this downturn is different compared to the dot-com bubble? Why was there more hope and promise coming out of the dot-com bubble?

2.) Income Inequality, The Rise of Depression & The Role of Politics:

  • Why is income and wealth inequality more concerning than ever? Why does Albert believe universal basic income is the right solution?
  • Why is mental health worse than ever? What can be done to improve this?
  • Why are our politicians failing us? What should our politicians be doing?
  • How does the rise of Trump show us what society is looking for in politicians?

3.) Climate Change: Misnomers, Developing Countries, Civil Disobedience:

  • What are the single biggest misnomers people have when it comes to climate change?
  • How can we shift spending on climate change solutions from 5% of GDP to 50%? Is that possible?
  • Why do developing nations have an advantage when implementing climate change solutions over more developed economies?
  • Why is civil disobedience the right course of action to ensure society is on a path to change our approach to climate change?

4.) Crypto and Central Banks: The Future of Finance:

  • Why does Albert believe that over the past few years, for many, crypto was a good hedge against inflation?
  • How damaging does Albert believe SBF and FTX will be to crypto in the long term?
  • How does Albert evaluate the potential for governments to create a "central bank digital currency"?
  • What would Albert like to see in a potential currency like this? How could stable coins be the solution to this? What is Albert fearful of with central bank digital currencies?
  • Why does Albert believe now is the best time to be investing in crypto?

5.) The Future of Social Media: Twitter & TikTok:

  • What does Albert believe is wrong with Twitter today? Why was the blue check mark such a mess?
  • What does Albert believe Elon should do with Twitter from this point on? How should Elon deal with the debt providers he has?
  • What happens to Twitter moving forward? Why is it so hard to kill?
  • What is the future of TikTok? Will it be banned in the US?
  • How concerned should the consumer be concerning their data being shared with the Chinese Government?

Jan 20, 2023

Mike Cessario is the Founder and CEO @ Liquid Death, the man hacking the healthy beverage market with the first hilarious water brand. It is working, Liquid Death's latest valuation was over a staggering $700M and Mike has raised over $200M since founding the company from the likes of Science Inc. Away's Jen Rubio, Dollar Shave Club's Michael Dubin, Swedish House Mafia and Tony Hawk to name a few. Prior to founding Liquid Death, Mike was in the advertising industry at a number of dirrect firms including VaynerMedia.

In Today's Episode with Mike Cessario We Discuss:

1.) From Canned Water to $700M Business:

  • How did rockstars' hydration problems lead to the founding of Liquid Death?
  • How did growing up with guns and heroine needles around him at school, impact how Mike sees the world today? What is he running from? What is he running towards?
  • Everyone said, "canned water, that is a stupid idea". What does Mike tell to all entrepreneurs who are told their idea is stupid? How does Mike advise on picking your idea?

2.) How to Build a Truly Great Brand:

  • What does the term "brand" mean to Mike?
  • What does he mean when he says, "truly great brand transcends functional value"?
  • What are the single biggest mistakes Mike sees founders make today on branding?
  • Why does Mike believe people will always hate your brand, if it is good?
  • What are the biggest brand mistakes Mike has made with Liquid Death?
  • What brand does Mike most respect and admire? Why that brand?

3.) Marketing: The Secret to Reaching Millions of People with Little Budget:

  • How does the Liquid Death team come up with the ideas they have for content? Why does Mike believe the label "storytelling" is kinda BS?
  • Why does Mike believe people will always hate your marketing? What was Mike's biggest lesson from their Superbowl commercial with kids drinking Liquid Death, looking like beer?
  • How does Mike decide which channel to prioritise? How has the rise of TikTok and short form video changed their approach to content?
  • How does Mike approach resource allocation for new pieces of content? Do they spend big on few bits of content or spend little on many and see what works?


Jan 18, 2023

Hila Qu is one of the leading growth execs of the last decade. Hila helped scale Acorns from 1 million to 5 million users as their VP of growth. Hila then joined GitLab, where she launched their PLG motion (on top of an established sales motion), and built their first-ever growth team. Today Hila is an advisor to amazing companies like Replit and funds like Mucker Capital, Openview and First Round Capital.

In Today's Episode with Hila Qu We Discuss:

1.) From Biology and Explosions to Growth:

  • How Hila made her way into the world of growth with
  • What are 1-2 of the biggest takeaways from her time with Acorns and Gitlab?
  • How do B2B growth orgs compare to B2C growth orgs? What is different? What is the same?

2.) WTF is Growth? When? How & Why:

  • How does Hila define growth today? What is it not?
  • When is the right time for early-stage founders to hire their first growth hire?
  • Why does Hila always look for data analysts in this first growth hire?
  • From a data standpoint, what should founders have ready and accessible for their first growth hire to have access to and learn from? Is Google Analytics enough?

3.) Hiring Your First Growth Hire:

  • How should early-stage founders structure the hiring process for the first growth hire?
  • What do the best growth job descriptions include? What do they not include?
  • Once applications are in, how does Hila advise founders screen for the best candidates?
  • How should founders structure the interview process post-screening? What are the must-ask questions? Who is involved in the interview process? What are some red flags?

4.) The Master of Onboarding:

  • What should new growth hires want to achieve in the first week?
  • What should they want to complete in the first month?
  • In the first quarter, what do the best candidates have completed?
  • What can founders do to set their growth hires up for success in the best way at this time?

5.) Growth Models, North Stars, Activation and Onboarding and Key KPIs:

  • What really is a growth model? How do founders and growth teams create one?
  • How does Hila advise founders on how to pick the right North Star Metric to focus on?
  • Why are activation and conversion Hila's two favorite growth metrics?
  • What are growth loops? What are growth funnels? How do they work together?

Jan 16, 2023

Jeff Jordan is a General Partner @ a16z where he serves on the boards of Airbnb, Incredible Health, Instacart, Lookout, and Pinterest, just to name a few. Before a16z, Jeff was CEO OpenTable, where he led the company during a period of hyper-growth and oversaw its IPO. Prior to OpenTable, Jeff was Senior VP and General Manager of eBay North America where he oversaw eBay's early growth into one of the Internet's leading commerce brands. In this role, he drove the successful acquisitions of PayPal and and went on to become President of PayPal, where he was responsible for establishing the company as the global standard for online payments.  

In Today's Episode with Jeff Jordan We Discuss:

1.) From Taking Opentable Public to Being a GP @ a16z:

  • What led to Jeff making the jump from CEO @ Opentable to becoming a GP at a16z?
  • How does Jeff believe his operating career impacted how he thinks and acts as an investor today, both positively and negatively?
  • What is his 1 biggest learning from eBay and then Opentable that has really shaped his mindset today as an investor? How did those experiences impact what he looks for in companies?

2.) The Two Core Features To Look For in Marketplaces:

  • Fragmentation of supply side: Why does Jeff look for fragmented supply sides? Does this not take longer and is more expensive? How fragmented is fragmented enough?
  • What are the most common reasons founders fail to acquire a fragmented supply side?
  • Intelligent Lead Generation: What does Jeff really want to see in the way that new marketplaces acquire their customers? How does this change with the rise of TikTok and short-form video?
  • What are some other really core features or traits that excite Jeff when he sees them in an early marketplace? What are some massive red flags for Jeff when he sees them early?

3.) How to Acquire and Retain the Demand Side of a Marketplace:

  • Messaging and Brand: What are the biggest lessons Jeff has on how to craft the messaging of a marketplace to make it resonate with the target consumer?
  • What are Jeff's biggest lessons from working with Brian Chesky on how they craft their messaging at Airbnb? What works? What does not work?
  • Perfect Customer Cohorts: What does Jeff most want to see when examining prospective marketplace investment cohorts? What do the best have?
  • What is the sign of a truly retained user in a marketplace? What is a good date duration to measure retention against? What are the biggest mistakes founders make presenting their cohorts?
  • Lessons from Instacart: What are Jeff's biggest lessons from being on the Instacart board on cohorts? What makes good cohorts? How cohorts can seem bad but be good?

4.) Growth vs Profitability, CACs and LTV:

  • Uber, OfferUp, Instacart, Deliveroo, respectfully, the level of profits these businesses are able to drive is questionable, why does Jeff believe marketplaces are good investments still?
  • Many marketplaces start with poor unit economics, how does Jeff think about having the mental plasticity to project out to a time when unit economics could be better?
  • Does Jeff pay attention to CACs at all? When are they important? When are they not? How can they be misleading? What is the best way for founders to present their CACs?

5.) It's Time to VC: Jeff Jordan: The Board Member

  • What are the single biggest misalignments between VCs and their founders?
  • How would Jeff describe his style of board membership today? How has it changed with time?
  • What is the best way to deliver hard feedback as a board member? What are the biggest mistakes board members make? What does Jeff advise young board members today?
  • What are the single best and worst changes that have happened at a16z in the last 24 months?

Jan 13, 2023

The question is: "are VCs still investing?". Today we are joined by Jason Lemkin; one of the OGs of SaaS of the last decade. As the Founder of SaaStr, he has inspired more SaaS founders than one can imagine building “The World’s Largest Community for Business Software.” Jason also invests out of the $100M SaaStr Fund and in the past Jason has led rounds into TalkDesk, Pipedrive, Algolia, Gorgias, Salesloft, and many more incredible companies. Prior to founding SaaStr, Jason was the Co-Founder of Echosign, an early e-signature business, funded by Emergence Capital and that was acquired by Adobe for $100M.

In Today's Episode on "Are VCs' Still Investing" We Discuss:

1. What Does it Take To Get Funded Today:


  • How has what VCs want in early-stage investments changed in this new environment?
  • Should startups prioritize growth? Profitability? Capital efficiency?
  • How long a runway is sufficient enough for founders to feel comfortable?
  • Why does Jason believe most founders are still deluded that they are fundable?

Growth Stage Companies:

  • Is the growth stage totally dead?
  • What will we see happen to all the companies that raised $50M+ at large valuations that have very little revenue?
  • Why does Jason believe that any operator who joined a $BN company in the past few years will not make any money on their equity? What should they do now?
  • Will we start to see down rounds and structured rounds at the growth stage? If so, when?

Public Markets:

  • Why does Jason believe this is a time unlike any he has seen before?
  • Are we in full recession now in Jason's mind? In Dec 2023, will this be better or worse?
  • Which are the most under-priced assets in the public markets today?
  • Why does Jason believe VCs investing in public markets are losers?

2. Micro Funds Will Be Decimated and LP Behaviour in 2023

  • Why does Jason believe that micro-funds in 2023 will be decimated and unable to raise new funds?
  • How will the majority of LPs approach new fund investments?
  • How will LPs approach re-investing in their existing managers? How has what they need to see changed?

3. Marketing and Sales: We Need To Change Budgets and Targets

  • How should CEOS be changing their marketing budgets in 2023?
  • What are the single biggest mistakes CEOs are making in this downturn with regard to their marketing budget?
  • How do sales targets need to be amended in the face of changing buying patterns?
  • How do the best sales and marketing leaders respond to these changing budgets and targets? How do the worst respond?





Jan 11, 2023

How To Raise a Venture Capital Fund

Over the last 4 years, I have raised around $400M across different vehicles from many different types of investors. Today I am going to break down the early stages of how to raise a venture capital fund and then stay tuned for a follow-up to this where we will break down a fundraising deck for a fund, what to do, what not to do etc. But to the first element. 

Your Fund Size is Your Strategy:

The most important decision you will make is the size of fund you raise. So much of your strategy and approach will change according to your fund size target (LP type, messaging, documentation, structure etc). Remember, your fund size is your strategy. If you are raising a $10M Fund, you are likely writing collaborative checks alongside a follower, if you are raising a $75M fund, you will likely be leading early-stage seed rounds. These are very different strategies and ways of investing. 

MISTAKE: The single biggest mistake I see fund managers make is they go out to fundraise with too high a target fundraise. One of the most important elements in raising for a fund is creating the feeling of momentum in your raise. The more of the fund you have raised and the speed with which you have raised those funds dictate that momentum. So the smaller the fund, the easier it is to create that heat and momentum in your raise.

LESSON: Figure out your minimum viable fund size (MVFS). Do this by examining your portfolio construction. In other words, how many investments you want to make in the fund (the level of diversification) and then alongside that, the average check size you would like to invest in each company. Many people forget to discount the fees when doing this math and so the traditional fund will charge 2% fees per year and so across the life of the fund (usually 10 years), that is 20% of the fund allocated to fees. 


We are raising a $10M Fund. 

20% is allocated to fees for the manager and so we are left with $8M of investable capital. 

A good level of diversification for an early-stage fund is 30 companies and so with this fund size, I would recommend 32 investments with an average of $250K per company. That is the $8M in invested capital. Big tip, I often see managers raising a seed fund and are only planning to make 15 investments, this is simply not enough. You have to have enough diversification in the portfolio if you are at the seed stage. No one is that good a picker. Likewise, I sometimes see 100 or even 200 investments per fund, this is the spray-and-pray approach, and although works for some, your upside is inherently capped when you run the maths on fund sizes with this many investments. 

A big element to point out in this example is we have left no allocation for reserves. For those that do not know, reserves are the dollars you set aside to re-invest in existing portfolio companies. Different funds reserve different amounts, on the low end there is 0% reserves and on the high end some even have 70% of the fund reserved for follow-on rounds. 

In this example, given the size of the fund being $10M with a seed focus, I would recommend we have a no-reserves policy. Any breakout companies you can take to LPs and create SPVs to concentrate further capital into the company. This is also better for you as the manager as you then have deal by deal carry on the SPVs that are not tied to the performance of the entire fund.

So now we know we know $10M is our MVFS as we want to make at least 30 investments and we want to invest at least $250K per company. Great, next step. 

Set a target that is on the lower end, you can always have a hard cap that is significantly higher but you do not want the target to be too far away that LPs question whether you will be able to raise the fund at all. This is one of the biggest reasons why many do not invest in a first time fund, they are unsure whether the fund will be raised at all. 

The Team:

Alongside the size of the fund, the team composition is everything, simply put, LPs like managers who have invested in the stage you are wanting to invest in moving forward. They like to see track record.

IMPORTANT: I see so many angels write checks into breakout Series B companies and then go out and try and raise a seed fund with this as their track record. Do not do this, this does not prove you are a good seed investor but merely shows you have access at the Series B. These are very different things. 

With regards to track record, in the past, TVPI or paper mark-ups were enough, now there is a much greater focus on DPI (returned capital to investors). LPs want to see that you have invested before at that stage and they also want to see that the team has worked together before. You want to remove the barriers to no. If you have not worked with the partners you are raising with before, LPs will have this as a red flag, and as team risk, it is that simple. 

Navigating the World of LPs (Limited Partners)

The size of the fund you are raising will massively dictate the type of LPs that will invest in your fund. 

MISTAKE: You have to change your messaging and product marketing with each type of LP you are selling to. A large endowment fund will want a very different product to a Fund of Funds. 

Example: If you are a large endowment, you will invest in early funds but you want the manager to show you a pathway to them, in the future, being able to take not a $10M check but a $50M check from the endowment. Whereas the Fund of Funds will likely want you to stay small with each fund. So when discussing fund plans, it is crucial to keep these different desires in mind.  

If you are raising a $10M fund, you will be too small for institutional LPs and will raise from individuals and family offices. An LP will never want to be more than 20% of the LP dollars in a fund and so the size at which an institutional LP (really the smallest fund of funds) would be interested is when you raise $25M+ and they can invest $5M. Generalisation but a good rule of thumb to have. 

LP Composition of Your Fund:

Speaking of one LP being 20% of the fund dollars, it is helpful to consider the LP composition you would like to have for your fund. The most important element; you want to have a diversified LP base. A diversified LP base is important in two different forms:

  1. No LP should be more than 20% of the fund at a maximum. That said you do not want to have so many investors in your fund it is unmanageable. LPs need time and attention and so it is important to keep that in mind when considering how many you raise from. Some LPs will want preferred terms or economics for coming into the first close or being one of the first investors, if you can, do not do this. It sets a precedent for what you will and will not accept and then for all subsequent investors, they will want the same terms and rights. 
  2. You want to have a diversification of LP type (endowments, fund of funds, founders, GPs at funds etc). Why? In different market cycles, different LPs will be impacted and so if you only raise from one LP type, if a market turns against that LP class, then your next fund is in danger. 


We will see the death of many mico-funds ($10M and below). Why? The majority raised their funds from GPs at larger funds and from public company founders. With the changing market environment, most GPs are no longer writing LP checks and most public market founders have had their net worths cut in half by the value of their company in the public market and so likewise, are no longer writing LP checks. In this case, the next funds for these funds will be in trouble as their core LP base is no longer as active as they used to be. We are seeing this today. 


  • 50% of the micro-funds raised in the last 2 years will not raise subsequent funds.  

Going back to the question of diversification, my preference and what we have at 20VC, the majority of dollars are concentrated from a small number of investors. Of a $140M fund, we have $100M invested from 5 large institutions. These are a combination of endowments, Family Offices, a High Net Worth Individual and a Fund of Funds. The remaining $40M originates from smaller institutions or individuals, for us we have over 50 making up that final $40M. For me, I really wanted to have a community around 20VC Fund and so we have over 40 unicorn founders invested personally in the fund as LPs. 

Bonus Points: The best managers select their LPs to play a certain role or help with a potential weakness the manager has. For example, I was nervous I did not have good coverage of the Australian or LATAM startup market and so I was thrilled to add founders from Atlassian, Linktree, Mercado Libre, Rappi and Nubank as LPs to help in regions where I do not have such an active presence. If you can, structure your LP base to fill gaps you have in your ability.

Status Check In:

Now we know our minimum viable fund size, we know the team composition we are going out to raise with, we know the LP type that we are looking to raise money from and we know how we want our desired fund cap table to look. 

Now we are ready to move to the LPs themselves. 

Fill Your Restaurant with Friendlies:

As I said, the appearance of your raise having heat and momentum is important. 

Mistake: The biggest mistake I see early fund managers make is they go out to large institutional investors that they do not have an existing relationship and spend 3-4 months trying to raise from them. They lose heat, they lose morale and the raise goes nowhere.

Whatever fund size you are raising, do not do this. Fill your restaurant with friendlies first. What does this mean? Go to anyone you know who would be interested in investing in your fund and lock them in to invest. Create the feeling that progress is being made and you have momentum. 

BONUS POINTS: The best managers bring their LPs with them for the fundraise journey. With each large or notable investor that invests in your fund, send an email to the LPs that have already committed to let them know about this new notable investor. This will make them feel like you have momentum, they are in a winner and many will then suggest more LP names, wanting to bring in their friends. 

MISTAKE: Do not set a minimum check size, some of the most helpful LPs in all of my funds have been the smallest checks. Setting a minimum check size will inhibit many of the friendlies from investing and prevent that early momentum. 

The bigger the name the incoming investor has the better. You can use it for social validity when you go out to raise from people you know less well or not at all. Different names carry different weight, one mistake I see many make is they get a big name invested in their fund but it is common knowledge to everyone that this LP has done 200 or 300 fund investments, in which case, it does not carry much weight that they invested in your fund. Be mindful of this as it can show naivety if you place too much weight on a name that has invested in so many funds. 

Discovery is Everything:

The world of LPs is very different to the world of venture. 99% of LPs do not tweet, write blogs or go on podcasts. Discovery is everything. When I say discovery I literally mean finding the name of the individual and the name of the organization that is right for you to meet.  

This can take the form of several different ways but the most prominent for me are:

  1. The Most Powerful: Create an LP acquisition flywheel. What do I mean by this? When an LP commits to invest in your fund. Say to them, “thank you so much for your faith and support in me, now we are on the same team, what 3 other LPs do you think would be perfect for the fund?” Given they have already invested, they already believe in you and so 90% of them will come back with 3 names and make the intro. Do this with each LP that commits and you will create an LP acquisition flywheel. 

Bonus Point: The top 1% of managers raising will already know which LPs are in the network of the LP that has just committed and will ask for those 3 specific intros. They will then send personalized emails to the LP that has just committed. The LP is then able to forward that email to the potential LP you want to meet. You want to minimize the friction on behalf of the introducer and so writing the forwardable email is a great way to do this. 

  1. The Most Likely to Commit: LPs are like VCs. When one of their portfolio managers makes an intro and recommendation to a potential fund investment, they will place a lot more weight on it than they would have otherwise. So get your VC friends to introduce you to their LPs, it is that simple. Remember, you have to remove the friction from the introducer. So, make sure to send the email they can forward to the LP. Make this personalized and concise.

Mistake: Many VCs do not like to introduce other managers to their LPs as they view it as competition. This is moronic. If the manager asking for the intro is really good, they will raise their fund with or without your intro. If they are not good, then you can politely say it would not be a fit for your LP and move on. Do not be too protective of your LPs from other managers.

  1. The Cold Outbound: I am not going to lie cold outbound for LPs is really hard. Here is what I would suggest:

  • Pitchbook: It is expensive and many cannot afford it but if you can, it is worth it for LP discovery. They have thousands of LPs of different types on the platform all with their emails and contact details. Those are less useful as a cold email to an LP is unlikely to convert but just finding their names and the names of their organization is what is important. You can then take that to Linkedin to then find the mutual connections you have with that person and ask for a warm intro. 
  • Linkedin: Many LPs have the funds that they have invested in on their Linkedin profiles with the title “Limited Partner”. If they are invested in a fund that is aligned with the strategy that you are raising for, there is a strong chance they might be a fit. For example, I invest in micro-funds and have invested in Chapter One, Scribble, Rahul from Superhuman and Todd’s Fund, and Cocoa Ventures, so you see this and see I like sub $25M funds with a specific angle. 
  • Clearbit: Often you will know the name of the institution but not the name or position of the person within the institution that you are looking to raise from. Download a Google Chrome Plugin called Clearbit. With Clearbit you can simply insert the URL for the organization you would like to speak with and then all the people within it will appear and you can select from title and their email will be provided. Again, if you do not want to cold email, you now have their name which you can take to your community, to ask for the intro. 

MISTAKE: LPs invest in lines, not dots. Especially for institutional LPs, it is rare that an institution will meet you and invest in you without an existing relationship and without having followed your work before. A mistake many make is they go to large institutions and expect them to write a check for this fund, it will likely be at best for the fund after this one or most likely the third fund. This does not mean you should not go to them with your first fund but you should not prioritize them and you should not expect them to commit. I would instead go in with the mindset of we are not going to get an investment here, so I want to leave the room understanding what they need to see me do with this first fund, to invest in the next fund. The more detailed you can get them to be the more you can hold them to account for when you come back to them for Fund II. 

Example: If they say, we want to see you are able to price and lead seed rounds and we are not sure you can right now. Great. Now when you come back to them in 12 months' time, you can prioritize the fact that you have led 80% of the rounds you invested in, and their core concern there has been de-risked.

In terms of how I think about LP relationship building, I always meet 2 new LPs every week. I ensure with every quarter, I have a check-in with them and ensure they have our quarterly update. This allows them to follow your progress, learn how you like to invest, and communicate with your LPs. It also really serves to build trust. Doing this not in a fundraising process also removes the power imbalance that is inherent within a fundraise and allows a much more natural relationship to be created. 

Jan 9, 2023

Henry Schuck is the Founder and CEO @ ZoomInfo. From ZoomInfo's founding moment, putting $25,000 on a credit card, Henry has led the company to today, with over $1BN in ARR, a market cap of over $10BN, and a team of over 3,600. This is one of the untold but truly great stories in software.

In Today's Episode with Henry Schuck We Discuss:

1. From a $5,000 College Fund to Founding a $10BN Company:

  • Why did Henry always believe early in life that he would be successful?
  • Along the way doubt sets in, what did Henry do to combat that doubt when he questioned his own ability and potential?
  • What does Henry believe he is running from? What is he running towards?
  • How did seeing the work ethic of his single mother impact his work ethic with ZoomInfo?

2. Henry Schuck: The Leader:

  • What does Henry believe is the difference between trust vs safety in team culture?
  • Why does Henry believe safety is built through performance? How does Henry manage and communicate underperformance? How long do you give an under-performer?
  • Why does Henry believe that happier teams outperform? What does Henry do deliberately and specifically to drive happiness in the business?
  • ZoomInfo is magnitudes larger than some competitors who receive a lot more attention, how does Henry think about this? How does he manage his own ego as a leader today?

3. Henry Schuck: A Leader in a Changing Market:

  • How does Henry maintain internal morale when employees see their stock options get smashed every day?
  • Does it suck to be a public company CEO in the current market? What element is the worst?
  • How are the buying patterns and behaviors of customers changing in 2023 vs 2021?
  • How does this impact the sales cycle, retention rates, upsell plans, and the structure of the customer success teams?
  • Dec 2023, will we be in a better or worse macroeconomic position?

4. Henry Schuck: Relationship to Money and Fatherhood:

  • How does henry evaluate his relationship with money today? How has it changed over time?
  • Why does Henry very rarely fly private planes? What does he believe this says about his values?
  • How does Henry instill the same desire and worth ethic within his children despite being a billionaire?
  • What does Henry know now that he wishes he could give to his 23-year-old self founding the company?

Items Mentioned in Today's Episode:

Henry's Favourite Book: The Happiness Advantage: The Seven Principles of Positive Psychology that Fuel Success and Performance at Work

Jan 6, 2023

Jason Fried the Co-Founder and CEO at 37signals, makers of Basecamp and HEY. Over an incredible 21-year journey, Jason and his co-founder David have scaled Basecamp to become the communication tool trusted by millions. Jason is also the co-author of the widely acclaimed, ReWork and has also made several angel investments in the likes of Intercom, Gumroad and Hodinkee to name a few.

In Todays Episode with Jason Fried We Discuss

1. From Web Design Agency to Founding Basecamp:

  • What was the a-ha moment for Jason when they had to make the pivot from a design agency to going full-time launching and running Basecamp as a SaaS company?
  • What is Jason running towards? What is he running from?
  • What is the single biggest fear that Jason is trying to avoid?

2. Jason Fried: The Leader:

  • Why does Jason believe he is running from his position as leader and CEO @ Basecamp?
  • Why does Jason not like or agree with goals or targets? Why are they not helpful?
  • How does Jason make decisions today as a leader and CEO? What one question does he ask that determines his decision-making process?
  • Why does Jason never compare himself to the competition? Why does he believe competition is for losers?

3. Jason Fried: The Politicisation of Leadership:

  • Why did Jason and David decide to not allow politics in the workplace?
  • How did they manage with 1/3 of their team leaving overnight? How was that experience for them personally? How did it impact the company? Is there anything they would do differently?
  • Does Jason believe we will see the continued politicization of leadership in the coming months?
  • How would Jason advise other CEOs when it comes to taking a stance on politics?

4. Jason Fried: Building the Best Team:

  • What is the one question that determines whether you made a good hire?
  • Why does Basecamp start with hiring all employees on a week-long project contract?
  • Why does Jason believe the best CEOs approach management as the art of the individual?

5. Jason Fried: The Partner, Father, and Husband:

  • Jason and David have been partners for 21 years, why does Jason believe it is helpful that they do not see each other much?
  • Is it right for co-founders and partners to be friends?
  • What have been Jason's single biggest lessons on what it takes to be the best husband?
  • What does great fatherhood mean to Jason? How has it changed over time?

Dec 21, 2022

20VC: Fundraising 101

Today we are going to walk through the process of raising a funding round for a hypothetical company. We will break it down by different stages in the fundraising process and at those stages I will talk about how each element differs according to the round being raised. 

First, for 99% of fundraises it is a game of shots on goal. You need to have enough investors in the pipeline, it is a sheer numbers game. Miki Kuusi @ Wolt said on 20VC recently for his Series B he got 68 rejections before Laurel Bowden @83North said yes. Wolt sold in 2021 for $7BN to Doordash making a monster return for the company's investors. But 68 meetings before that yes, for the Series B. Also goes to show, you sometimes just need one true believer. 

How to Create a Target List of Investors

Now we know we need enough shots on goal, we need to bring together a target list of investors, put these investors in three buckets:

  1. Priority (5 names of people you really want.)
  2. Tier 2 (15 names of people you would like)
  3. Tier 3 (15 names of people you would take money from but would not invite to your birthday!) 

So how do we choose who goes in what bucket? First, founder references speak volumes and lead to warm intros, so speak to your friends who are founders, ask which of their VCs have been the best, place even more weight on their recommendation if the company has not been a success. It is easy to be a VC champion when the company is flying, you often see the true colours of the VC when a company is really struggling or fails. Get a couple of names there and then analyse the VC landscape, you can do this on Twitter or the VCs website or blog and find the VCs that resonate best with your company. Look at the types of deals they have done before, are they interested in pre-seed fintech in Europe, do they do enterprise SaaS Series A in the Silicon Valley. You can see their portfolio, make sure it is a fit for them. I get about 200 inbounds per day across channel, about 150 are clearly not a fit for me because of stage, sector or location and so making sure the obvious are aligned is crucial. Then double down on their Twitter or public profile to see as much as you can about their values and how they portray themselves. Rule No 1, never work with assholes. Value alignment is really important. Now we have the five priorities and then I would say do the same for the Tier 2 and Tier 3 bucket, make sure they invest both in your stage, sector and geography. 

The Biggest Mistakes Founders Make Pitching:

So now we have our pipe of investors. A couple of big mistakes I see founders make in this next step. 

  1. They go to their priority names first. Do not do this. Your pitch both in delivery, style and messaging will improve so much with each meeting. Start with a couple where you would not be sad if they said no. Analyse in real time in those meetings what messages are hitting and what are not, where are investors spending the majority of the time, are there common questions that keep coming up. If so, create an FAQ page that is in the deck and that will prevent you from having to answer the most obvious in other meetings. With each meeting, you will find ways to iterate the deck, the messaging and the way you present. 
  2. Another massive mistake founding teams make, if you are doing a Zoom call and it is a first meeting, do not have more than 2 people on the call from your team. It makes it tough to get to the core of the discussion and removes a lot of the relationship building with too many people too soon. If the investor likes the opportunity, they will ask to meet more team members but do not put too much in front of them to the point it dilutes the message and pitch. 

Now we have done the first investor meetings and we have iterated our deck and messaging in accordance with the feedback we got. We now progress to taking meetings with investors we want as our partners. 

How to Master the Subtleties of a First VC Call:

  1. Every investor call usually starts with each side telling a little about themselves and how they came to be the founder or the VC. As the founder, practice your intro, make it succinct, concise, break it into three chapters, a minute per one is a good guidance. In these you want to show a couple of things, founder <> problem fit or in other words, why you specifically have the right experience or skills to attack this problem. I also like to understand “insight development” as taught to me by the famous OG of seed investing, Mike Maples @ Floodgate. Insight development is the notion that the best companies are founded on a unique insight that the founder has about a product or market that is different to the way the world currently sees it. Include these two in your intro. Keep the intro to no more than 3-4 mins. 
  2. For the VCs intro, it is important to try and understand a little more about them. Many VCs give boring and bland intros; “we do Series A and B in Europe and like to lead rounds.” Very standard response and so you should ask them how they like to work with their founders, ask them about a company that struggled and how they worked with the founder to help. Ask them about their decision making process for reserves and pro rata. This creates more of a conversation which will instantly give you as a founder more gravitas in the eyes of the VC. 
  3. Use the deck as a vitamin and not a painkiller. I hate pitches where it is read off slide by slide. I would not have the slides showing at all, I will have asked for a deck pre the meeting and I should have gone through it before. The call is for me to ask about questions I want to understand more or double click on. That said, the deck can often be useful as a crutch and so it can work well to have it ready and refer to certain slides as and when necessary. 


The 7 Sins of Fundraising Decks:

So while we are on the deck, I want to go through a couple of elements that I so often see and they are killer mistakes:

  1. Length: Keep the deck less than 10 slides. If you need a couple more to show data or additional research, put it in the appendix at the end of the deck. 
  2. Introduction: First slide, company name and then answer the question; if I had a billboard in Times Sq, what would it say on it? 10 words max. From your first slide alone, there should be no doubt about what your company does. 
  3. The Team Slide: where do people go wrong here. They put 12 faces on it with their names. No information about the people, where they worked, why they are the best team to solve this problem. A totally useless slide if done like this. So do not do this. Instead, take 4 of those people, break the slide into quadrants and expand on those 4 people’s backgrounds to why they are perfectly suited to do what they are doing. Fewer people more context. 
  4. The Useless Advisor Slide: Aligned to the terrible pictures of many team members with no context, the advisor slide, honestly, advisor slides just carry such little weight these days, they are not worth having. Take it out, it is not needed. 
  5. Market Sizing Errors: This is a massive one. I see so many make the mistake on market size slide. Say we have a CRM for hairdressers, taking a very random example here, so often I will see a $100BN market, thats the TAM for the hairdressing market or the CRM market, but we are CRM for hairdressers so that is not the right representation and is entirely misleading. It is much better to start with that, then show the slither of wallet spend that hairdressers spend on software and then show the even smaller slither that they spend on CRMs. Use the market sizing slide as a way to show your insight and intellect both into how the market is carved up today but also how it is going to change in the future. There is always the debate of what matters more, large market or amazing founders, the truth is, a massively growing market can cover a lot of operational sins and so showing how the market is and will expand and what causes this, the why now, will always be important. But do not show the massive market for hairdressing or whatever it is, I have seen more $1TN TAM for pet grooming businesses that you can imagine. So do not do that. 
  6. Exit Slides are Terrible: I do not see this so often now but do not have an exit slide in the deck for your early stage company, the wrong type of investors will be attracted to you if they like this slide, it encourages short term thinking and is not the right way to present for a company that will reshape an industry so no exit slide. 
  7. Why You Should Not Invest: One thing I love in startups and always have when I present my funds is a slide, why you should not invest in me. I think the most important thing for all founders is to be aware of their biggest weaknesses and then have clear action plans on what they are doing to mitigate the chances of them impacting their success. So have a slide that says, hey, these are our 3 biggest weaknesses and then tied to each one, this is what we are doing to solve it. This inspires trust in the relationship with the investor and really shows your self-awareness and strategic thinking.

How To Structure The Size and Composition of Your Funding Round:

Now at some point in the discussion the size of the round and the price of the round will be asked. Use this as a chance to show your calibre as a founder. 

  1. You Cannot Sit With Us (You Get The Joke!!!): Massive mistake founders make is they structure a round that does not allow for a VC to invest. What do I mean by this? VCs that lead rounds need to own at least 8% very minimum and if you come in raising $2M on a $25M cap, that is not enough allocation for the VC and pro-rata amount and then angels as well. Do not prohibit the VC from investing because of the structure of your round. For that example, $5M on $25M would allow for the VC to have 12.5% ownership, a smaller fund to have 3-4% and then a 3-4% allocation for angels. 
  2. Is This Check Meaningful?: An important question to ask is: is the check size being invested by the lead a material check size for them and their fund? For example, if the check size they are investing is less than 1% of their fund, it is not that meaningful, if it is less than .5%, it really is not meaningful. Now this could be bad as it means they are unlikely to be able to provide you with the same time and attention they would larger checks. That said, Jason Lemkin has also commented before on the benefits of this as they will leave you alone to execute, they will not put much pressure on you as you are not a core position and it is really yours to execute from there. 
  3. Do Not Do a Range: In terms of the actual size of check being raised, I do not like ranges. There is a massive difference between 3 and 5 million, and that impact on your runway is huge and so state a clear and direct number you are raising and what runway that will provide. 
  4. Milestone Hitting and Showing Resource Allocation: Use the question of how much are you raising to show your insight into the milestones that you need to hit over the next 18-36 months. Never raise less than 18 months, you also do not need to raise more than 36 months. Plan for a 6 month fundraise and execution 99% of the time always takes longer than you anticipate. With that in mind, I always prefer 24 months as the right period to raise for, this will give you 18 months heads down execution and then 6 months to raise. 
  5. Fundraising Rounds are To Prove Hypotheses: If we assume that fundraising rounds are science experiments and you have to prove or disprove a set of hypothesis with this time and money, make sure you can clearly articulate what you need to prove and by when. For the love of god do not say, this is the last round we will ever need to raise before we are immensely profitable, I could have a fund the size of Softbank if I had a dollar for everytime someone said that to me. 

How to Answer the Question of Valuation:

When you say the size of the raise, say $2M, the basic assumption is that each round will dilute 15-20% and so the average VC will think of a $10M post money valuation straight away when you say a $2M raise. That said, you do not want to anchor yourself to a price, you are running a process as transactional as it sounds and I am not saying you want to optimise for price by any means but the majority of the time, it is best to say, “hey we are raising $2M and we will let the market decide on the price”. This is a great way to answer the question as this will not put anyone off, it will not anchor you to a price and it will also show you are savvy as to the raise process which any incoming investor should want to see as your ability to raise the next round is fundamental for them. Again, use this question to show your sophistication and knowledge as to the finer details of how to navigate a fundraise successfully. 


How to Choose Your Lead Investor?


The biggest problem of the last 2 years was people chose their lead having met them once. They will be a partner to you for 10 years and you will not be able to get rid of them, it is literally harder to remove an investor than it is to get divorced. Brian Singerman @ Founders Fund said on the show recently about how he was unable to do his job in COVID as he could not meet founders in person. It is so important to meet your lead investor in person before signing the deal, so much can be gained and learned from those meetings in person. Then there is the question of how do I really get to know someone, especially if it is in a compressed timeline, there are ways that you can accelerate a relationship and getting to know someone, make sure to ask:

  1. What would success look like to them with this investment? What are the 1-2 core ways they believe that you will not achieve your outcome? What worries them?
  2. Can they give you a reference for founders they have worked with where it has not gone to plan? Also do off sheet references and try to find others where it did not go to plan. You can find their email with the Google Plugin by Clearbit and that is super easy. That should reveal alot. 
  3. I also find really being vulnerable, talking about ambitions, inspirations, fears, childhood, my mother has MS and it is a tough and horrible thing to see your mother suffer with, I will discuss that and how it has changed me and my mindset in many ways. 

How to Set a Timeline in a Fundraise?

In this deliberation phase where you are waiting for a term sheet, you do need to create some form of urgency. Investors often need a reason to move and so it is good to put a timeline on the raise. 14 days is perfect, this is enough time for any VC to do the work they need to do but also if they cannot do it in that time without a plausible excuse, it is unlikely that they would have done the deal and so it will force timewasters to a no sooner and save you time. 

Your Term Sheet is Ticking:

One thing to be wary of is exploding term sheets. If any VC says you have to sign this here and now, that is BS. Do not do it and that is no way to start a 10 year relationship. That said, it is fair for them to set some form of timeline, otherwise, you can shop the term sheet; share it with everyone and use the first people to commit as leverage to create FOMO to get other people to commit. This can be a disadvantage of being a first mover as a VC but that is why they will often have some form of expiry date and that is not unreasonable. 


When You Have Multiple Term Sheets: KISS (KEEP IT SIMPLE STUPID)


Then you have leverage and you can optimise the round on price, size of round, size of lead check to angel allocation etc etc. My advice here would always be do not over optimise. If the chosen partner is slightly lower, take it. Do not lose the right partner because of a small 5% difference in price or size of round. Another big mistake founders make when they have multiple term sheets is communication. It is fine if you need another couple of days to consider the decision but keep everyone updated. Let each investor who is waiting know, you are still thinking it through and will be back to them shortly. Name when you will have an answer, a communicated delay is fine, no communication is not. Then another massive mistake founders make is for the VCs they choose not to go with, they do not turn them down graciously. These investors could likely fund your next round, a bridge round and you never know when you might need them and so always turn them down super well and keep them on side, they could be helpful in the future.

If a VC Does These 3 Things: Forest Gump It: 

Now the massive red flags with leads in this process that we need to call out:

  1. Pay to Pitch: If any VC ever makes you pay to pitch them. This is unacceptable and we have to remove this from the industry. Tweet me the details of these investors, it can be anonymous but these bad actors need to be called out.
  2. Investment Tranches Kill Companies: If it is an early round and they want to do the investment in tranches. No. This is such an inhibitor for the business it will not allow you to allocate resources effectively or with confidence. Do not allow for tranches. A bad deal can sometimes be worse than no deal. Tranches does not set you up to execute against a plan, build a world class team and achieve what you can. Say no. 
  3. Early Signs of Excess Control and Ego: If they haggle immensely on salary over small amounts, if they suggest you should be on $60K not $62K and they make a big deal out of it. This is a sign of what they will be like to come. Do not accept it. 

So now we have our lead VC locked in and we have to allocate the rest of the round. I would work hand in hand with my VC to construct the rest of the round. They will have angels they work closely with and think highly of. Use them to help map out those people and then make those intros for you. 

How to Allocate Your Angel Allocation:

Assemble your angel cap table as you would a sports team. Each person has a specific position which they are specialised to and have a world class skill in. Someone for marketing, hiring, regulation, PR, partnerships etc. A massive mistake I see so often is founders try to cram down all their angels to their smallest allocation so they can fit as many as possible. Do not do this. Give fewer people more allocation. The only thing that matters is that the check size matters to them. For some it will be $10K for others it could be $50K but fewer with more skin in the game is important. 

Next I see so many founders drag out the process meeting just one more investor and just one more, after a certain time, just get it done, get it closed and move on. 

Just Closed: Time to Prep for the Next Round

So now we have closed the round, congrats. Now time to start prepping for the next round, one thing to remember, as a founder, you are always raising. So here is what we should do next:

  1. Sit down with our new lead investor and align on what we believe we need to hit to unlock the next round of funding. Will that next round come from them or external financing? 
  2. If external financing, what 5 names should we focus on?
  3. Make sure to send those 5 names monthly updates with your progress. Investors invest in lines not dots. 
  4. Make sure to meet them on a quarterly basis. 
  5. By the time of your next fundraise, following 6 face to face meetings and 18 updates, the investor and you will know if this is a partnership you want to pursue. 

I want your feedback. Did you enjoy this post? Let me know on Twitter here. 

Dec 19, 2022

Barry McCarthy is Peloton’s CEO and President. McCarthy is a seasoned executive who served as CFO of Spotify from 2015 to January 2020, and CFO of Netflix from 1999 to 2010. Prior to Netflix, McCarthy held various leadership positions in management consulting, investment banking, and media and entertainment. McCarthy has served on the boards of directors of Spotify and Instacart since January 2020 and January 2021, respectively. In addition, McCarthy has served as a member of the boards of Chegg, Eventbrite, MSD Acquisition Corp, Pandora, and Rent the Runway. 

In Today's Episode with Barry McCarthy We Discuss:

1. From Netflix to Spotify to Leading Peloton:

  • How did Barry make his way into the world of startups and come to work with Reed Hastings at Netflix? What are his single biggest takeaways from working with Reid?
  • Why did Barry decide to move to cold Stockholm to work with Daniel Ek and Spotify? What makes Daniel the special leader that he is?
  • Was Barry nervous about assuming the role of CEO @ Peloton? Are the elements he was most worried about the elements that are his biggest challenges today?

2. Barry McCarthy: The Leader

  • What does "high performance" in business mean to Barry?
  • Daniel Ek has described Barry as the "most strategic dealmaker in the world". What does Barry believe makes him so good at dealmaking? Where do so many go wrong?
  • Barry pioneered the model of the direct listing, why does he believe they are better? Why was it right as an approach for Spotify? Will we continue to see more?
  • What is Barry's framework for making tough decisions? How has it changed over time?

3. Barry McCarthy: The Master of Boards:

  • Barry has sat on some of the best boards from Netflix to Spotify to now Peloton and Instacart, what does Barry believe makes the best boards?
  • Where do many boards go wrong? Where do they become dysfunctional? What can and should be done to stop that?
  • How does Barry advise other board members on the right way to deliver tough news constructively?
  • What is the single biggest advice Barry would give to young board members assuming their first boards? Where do many young board members go wrong?

4. Barry McCarthy: Mastering the Mechanics:

  • Daniel Ek suggested that I had to ask about “demand creation theory and your ideas about whether the market is efficient”. What did he mean by this? How does Barry think about it?
  • How does Barry think about the interplay between gross margin, experience and retention?
  • Why did Barry decide it was the right decision to evolve the strategy from owning distribution to working with Amazon etc?

Dec 16, 2022

Hadi Partovi is a tech entrepreneur and investor, and CEO of the education nonprofit Before founding, Hadi founded two prior startups: Tellme Networks (acquired by Microsoft, discussed on 20VC with Emil Michael), and iLike (acquired by Newscorp). Hadi has also been an active advisor and angel investor to some of the best including FacebookDropboxairbnb, and Uber. If that was not enough, Hadi currently serves on the Board of Directors of Axon and MNTN.

In Today's Episode with Hadi Partovi:

1.) From the Iran-Iraq War to Founding Startups:

  • How Hadi and his family made their way from war-torn Tehran to the US and Silicon Valley?
  • How did seeing his family have nothing and struggle financially impact Hadi's mindset as an entrepreneur?
  • What does Hadi believe he is running from? What is he running toward?

2.) Lessons from Ballmer and Zuckerberg:

  • How did Hadi first come to meet a young Mark Zuckerberg when TheFacebook had less than 10 employees? Why did Hadi believe he was so special from that first meeting?
  • What are Hadi's biggest takeaways from working with Steve Ballmer? How did the reign and leadership of Ballmer compare to the reign of Bill Gates?
  • Hadi has helped both Facebook and Dropbox with their engineering hires, what is the secret to hiring amazing engineers? How does he structure the process? Where do so many go wrong?

3.) Hadi Partovi: The Leader:

  • How does Hadi define "high performance" in leadership? How has it changed with time?
  • What is Hadi's framework for making tough decisions? How does Hadi teach that framework to his team? What are the biggest mistakes leaders make in decision-making?
  • How important does Hadi believe speed of execution is? How does Hadi determine when is the right time to go slow to go fast?

4.) Hadi Partovi: The Person:

  • How does Hadi analyze his relationship with money today? How does it change over time?
  • Hadi stepped off the for-profit treadmill with, why did he make that decision? How does he avoid the trappings of chasing wealth?
  • How does Hadi think about ego and ego management today? How does Hadi separate self-worth from financial gain and accomplishment?

Items Mentioned in Today's Episode:

Hadi's Favourite Book: Sapiens: The #1 bestselling journey through human history and anthropology

Dec 14, 2022

Maggie Hott is the Director of Sales @ Webflow where she leads their Sales Dev, Account Executive, and Solution Engineering orgs. Prior to Webflow, Maggie spent an incredible 6 years at Slack in a period of hypergrowth for the company having joined as the founding AE scaling to a Sr Enterprise Leader. Before Slack, Maggie was the founding Sales hire at Eventbrite. If that was not enough, Maggie is also an active angel investor, an advisor to Cowboy Ventures, Scribble Ventures, and is a Founding Operator and LP @ Coalition Partners.

In Today's Episode with Maggie Hott We Discuss:

1. The Cold Email that Led to a World-Class Sales Career:

  • How a cold email to Kevin Hartz @ Eventbrite led to Maggie's career in sales?
  • What are the 1-2 biggest takeaways from her time at Slack? How did they impact her mindset?
  • What does Maggie know now that she wishes she had known when she entered sales?

2. The Sales Playbook: PLG and Enterprise:

  • How does Maggie define the sales playbook? What is it? What is it not?
  • Is it possible for early-stage companies to do both enterprise and PLG at the same time?
  • When is the right time to add enterprise to a PLG motion?
  • What are the steps to build an outbound sales engine in enterprise? Where do many go wrong?

3. Building the Bench: Hiring Your First Sales Team:

  • Should founders look to hire a Senior Head of Sales first or a more junior sales rep?
  • Should they be hired one at a time? What are the benefits of hiring many at the same time?
  • What is the right process to hire your first sales hire?
  • What are the core traits and habits that make the first 10x sales hire?
  • What are the right questions to ask to unveil those characteristics?

4. Making the Machine Work: The Process:

  • What can sales leaders do to proactively build relationships with other parts of the org?
  • How can more junior sales reps build relationships with other functions?
  • Why does Maggie believe that mis-hiring can be a $1M mistake? What are the early signs that a new hire is not working out in sales? How does this differ for outbound?
  • Why is it dangerous to make your self-serve product too good?

Dec 12, 2022

Ben Chestnut is the Co-Founder of Mailchimp, the all-in-one marketing platform for small businesses. Last year, in Sept 2021 it was announced that Intuit would acquire Mailchimp for a reported $12BN. There are so many things to love about the Mailchimp journey to this point. First, Mailchimp was founded as the result of a side project of a design agency Ben and his co-founder, Dan, used to run. Second, Mailchimp is and has always been based in Atalanta, eschewing the notion you have to be in SF or NYC to build a massive business. Then third, they never raised venture funding for the business all the way until their $12BN acquisition. Ben led Mailchimp to over 1,200 employees and millions of global users.

In Today's Episode with Ben Chestnut We Discuss:

1. From Mama's Kitchen to the Smell of Business and Founding Mailchimp:

  • How did Ben turn a mediocre agency into the founding of Mailchimp? What was the a-ha moment?
  • At what stage of the business did Ben quit the agency and go all in on Mailchimp? What sign did he need that Mailchimp had true product-market fit?
  • When Ben's mother died, he bought every flower in the local town to commemorate her. How did Ben's mother impact the type of father and husband he is today? How did she impact the way that he led Mailchimp as CEO?
  • Ben's fishing trips with his father played a big role in his early years, what were the single biggest lessons for Ben from his fishing trips with his father?

2. Ben Chestnut: The Leader:

  • How does Ben define the term "high performance" in leadership?
  • What does Ben mean when he says "the secret to happiness is to stay in your lane"?
  • Why would Ben describe himself as the "leader of the misfits"? How did that early experience and labeling impact both the people he hired and the culture he created at Mailchimp?
  • What does Ben mean when he says he used to have a "hands off, eyes off" leadership style? What have been the single biggest drivers in his development as a leader?

3. Ben Chestnut: The Person:

  • Relationship to Money: How does Ben reflect on his relationship to money? How has it changed over time? Why does Ben still to this day buy lottery tickets with his wife?
  • Conquering Fatherhood: What does being a great father to Ben mean? How does Ben attempt to instil the same work ethic and drive when his children are born into immense wealth?
  • The secret to Marriage: What does Ben believe is the core to a successful and thriving marriage? How does Ben view his role in the marriage? How has it changed over time?
  • Potential Lost Identity: A founder's identity is so closely tied to their company, how did Ben manage the challenge of selling his company but retaining his identity? What did Ben learn about himself through many different acquisition processes?

4. Mailchimp: The Business:

  • Why did Ben never raise venture money in the 21 year journey of Mailchimp?
  • Why did Ben never accept any of the acquisition offers that came before Intuit?
  • How did Ben motivate his team after they knew each acquisition offer was being turned down?
  • Why did Ben decide the acquisition by Intuit was the right decision for the company?
  • How does Ben view his role in the company now and moving forward?

Dec 9, 2022

Bob Pittman is Chairman and CEO of iHeartMedia, Inc., the number one audio company in America. Prior to iHeart, Bob has just had the most amazing career as a co-founder and programmer who led the team that created MTV. He has also led some of the most incredible turnarounds as CEO of MTV Networks, AOL Networks and Time Warner Enterprises and as COO of America Online, Inc. and later AOL Time Warner.

In Today's Episode with Bob Pittman We Discuss:

1. From Flying Lessons to Radio:

  • How Bob first made his way into radio at the age of 15?
  • What does Bob know now that he wishes he had known when he started his career?
  • What is the most painful lesson Bob has learned in his career that he is pleased to have learned?

2. Decision-Making in Leadership:

  • How does Bob structure all decision-making as CEO today?
  • Why does Bob ensure that all decisions are made within 24 hours? What are the pros and cons?
  • How does Bob prevent consensus decision-making? How does Bob create dissent in a discussion?
  • How do the best leaders know when to kill a project? What do most do instead?

3. Tactics vs Strategies: Why Plans Are BS!

  • What is the difference between a tactic and a strategy?
  • When is the right time to change your strategy and tactics?
  • What have been Bob's biggest lessons on how to get teams on board with tactical changes?
  • Why does Bob believe that plans are BS? When can they be useful?

4. The Secret to Messaging and Storytelling:

  • What does Bob believe is the universal truth to successful consumer messaging?
  • What has changed and what has not changed in the way companies tell stories to their customers?
  • Is there a difference between a great product and a great company? What are examples?
  • What excites Bob most about consumer habits today?

5. Bob Pittman: AMA:

  • What does Bob believe is the success to successful parenting? How has it changed?
  • How does Bob analyze his own relationship to money today? How has that changed?
  • Why does Bob not believe in legacy? What do people get most wrong when it comes to ego?

Dec 7, 2022

Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for some of the most successful companies in the world, including Hewlett-Packard, Netscape Communications, and eBay. He worked directly alongside Marc Andreesen and Ben Horowitz at Netscape and Pierre Omidyar at eBay.

In Today's Episode with Marty Cagan We Discuss:

1. Entry into the World of Product From Engineering:

  • How Marty first made his way into the world of product, having started life as an engineer?
  • What does Marty know now that he wishes he had known when he started in product?
  • What are Marty's biggest tips to anyone making the move from engineering to product?

2. Lessons from Marc and Ben at Netscape and Pierre @ eBay:

  • What are the single biggest lessons Marty took from working side by side on product with Ben Horowitz and Marc Andreesen?
  • What did Netscape do right? What did they do wrong? With hindsight, what would Marty have done differently?
  • How did Marty break all of his rules by working with Pierre Omidyar?

3. Hiring a World Class Early Product Team:

  • When is the right time to make your first product hire as a startup?
  • What is the right profile for that first product hire? Senior or junior?
  • If you go for the junior hire, how do you structure the rest of the team? If you go for the Senior hire, how do you structure the rest of the team?
  • What are the single biggest mistakes startups make when hiring their first in product?
  • Does Marty prefer someone with or without expertise in the domain you are in?

4. Mastering the Onboarding Process:

  • What is the optimal onboarding process for all new product hires?
  • How can leaders ensure that product hires see and understand all areas of the business?
  • What can product leaders do to proactively impress in the first 30-60 days?
  • What are clear red flags that a new product hire is not working out? How long do we give them?

Dec 5, 2022

Martin Casado is a General Partner @ a16z where he focuses on enterprise investing. At a16z, Martin has led investments and serves on the board of dbt Labs, Fivetran, Material Security, Ambient AI and many more incredible companies. Before venture, Martin was previously the Co-Founder and CTO at Nicira, acquired by VMware for $1.26 billion in 2012. While at VMware, Martin served as Senior VP and General Manager of the Networking and Security Business Unit, which he scaled to a $600 million revenue run-rate business.

In Today's Episode with Martin Casado We Discuss:

1. From $1.26BN Founder to Leading Enterprise Investing for a16z:

  • How did Martin make his way into the world of VC and come to lead enterprise investing for a16z?
  • What does Martin know now that he wishes he had known when he started investing?
  • What have been some of his biggest investing lessons from Marc and Ben?

2. The VC Model is Broken and Why:

  • Why does Martin believe that the current model for venture is broken?
  • Why does Martin believe that VCs are not oracles and they were not gifted with picking ability?
  • How will asset allocation more broadly fundamentally change over the next decade? Why will Silicon Valley take over and run Wall St?
  • Why does Wall St not care about innovation and true technological development?
  • Who will be the winners and who will be the losers in the next 10 years of venture?

3. Surviving a Crash - What Founders Need To Know:

  • Layoffs: What is Martin's advice to founders on doing layoffs today? How much is the right amount to cut? Should it be done in one go? How should this be communicated to investors and the board?
  • Scenario Planning: What three scenario plans should all founders be creating right now? How should they know which one is the right one to execute against?
  • Comparisons: How should founders use and look to public company performance and market cap to determine which plan they should choose?
  • Hiring Freeze: Why does Martin believe the biggest companies in the world make massive mistakes by freezing hiring? What should they do instead?

4. The Changing Guard at a16z:

  • What have been the single best and worst changes a16z have made over the last 24 months?
  • What are the first things to break when a firm scales as fast as a16z has done?
  • Does Martin agree a16z returns will reduce with the scaling of their funds larger than ever?
  • How does Martin look to train and educate his junior team? How does he advise them on surviving a downturn? What should they do? What should they not do?

5.) The Makings of a Great Board:

  • What are the three types of board members? What is the best? What is the worst?
  • What does Martin believe makes the truly great boards?
  • What is the biggest advice Martin gives to young board members today?
  • How has Martin changed as a board member over time? What does he need to improve?

Items Mentioned in Today's Episode:

Martin's Fave Book: The Weirdest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous

Dec 2, 2022

Will Hockey is the Co-Founder and Co-CEO @ Column, the only nationally chartered bank built to enable developers and builders to create new financial products. Before co-founding Column, Will was the Co-Founder, President, and CTO @ Plaid, a world-leading data network and payments platform. In 2020, Visa attempted to acquire Plaid for $5.3BN, however, this was blocked due to regulatory issues and the company went on to raise at a reported $13.4BN valuation just 9 months later. Additionally, Will is on the board of

In Today's Episode with Will Hockey We Discuss:

1.) The Founding of $13.4BN Plaid:

  • How did Will make his way into the world of startups and come to found Plaid with Zach?
  • If we are all a function of our histories, what is Will running from? What is he running toward?
  • What does Will know now that he wishes he had known when he started Plaid?

2.) Will Hockey: The Makings of a Decacorn Founder:

  • What does the term "high performance" mean to Will? How has this changed over time?
  • Having had such a successful time building Plaid to $13.4BN, how does Will assess his own relationship to risk and his relationship to money?
  • How does Will approach his own personal portfolio planning? Equity, debt, real-estate? How does Will optimize his own personal wealth?
  • Column is his second time founding a company, what did Will decide to take from Plaid that worked well? What did he decide he would not do having seen it work badly at Plaid?

3.) The Building of Truly Great Teams:

  • Why does Will believe that companies can be built so much slower than people think?
  • How does Will determine the decisions that have to be made fast vs those with time?
  • How does Will ensure the same size of urgency and speed within his team without this time or funding pressure?
  • What have been Will's single biggest lessons when it comes to people acquisition and retention?

4.) Fintech: The Next 10 Years:

  • How will the next 10 years look different from the last in fintech? What changes will be better? What will be worse? What is Will worried about? What is he excited about?
  • What does Will mean when he says, "the US financial system can function like a protocol"? What does Will believe are some of the core myths of the US financial system?
  • Why does Will believe the current financial system can and will fix a lot of what crypto is trying to solve? What barriers will prevent this from happening?

Items Mentioned in Today's Episode:

Will's Favourite Book: The World for Sale: Money, Power and the Traders Who Barter the Earth’s Resources, Merchants of Grain: The Power and Profits of the Five Giant Companies at the Center of the World's Food Supply

Nov 30, 2022

Jason Lemkin is one of the OGs of SaaS of the last decade. As the Founder of SaaStr, he has inspired more SaaS founders than one can imagine building "The World’s Largest Community for Business Software." Jason also invests out of the $100M SaaStr Fund and in the past Jason has led rounds into TalkDesk, Pipedrive, Algolia, Gorgias, Salesloft, and many more incredible companies. Prior to founding SaaStr, Jason was the Co-Founder of Echosign, an early e-signature business, funded by Emergence Capital and that was acquired by Adobe for $100M.

In Today's Episode with Jason Lemkin On Algolia We Discuss:

1.) Meeting the Unicorn: Algolia:

  • How did Jason first come to meet Nicolas (Founder) and Algolia?
  • What specific elements of cold emails make the best attract Jason's attention? What do they have in them? What are the most common mistakes people make with cold emails?
  • What is the single biggest mistake Jason made when making the deal with Algolia? How did Jason lead their seed round when their round was "oversubscribed"?

2.) Competition and TAM: The Reasons To Say No:

  • Competing with Free: How did Jason analyze the competitive landscape Algolia was facing? How did he gain comfort that they could compete and win against free and open-source?
  • TAM Analysis: The TAM at the time for Algolia was $2M. How did Jason analyze the TAM at the time? How did he get comfortable with such a small TAM?
  • What are the single biggest mistakes investors make when analyzing competition today? What are the biggest mistakes founders make when presenting the competitive landscape?
  • What are the single biggest mistakes investors make when analyzing TAM today? What are the biggest mistakes founders make when presenting the TAM and how it breaks down?

3.) Investing Lessons Transition from CEO to VC:

  • Jason has previously said one of his biggest lessons is "bet on what you know when you go from CEO to VC"? What did he mean by this?
  • How can one keep this operator knowledge and mentality when one is a VC for a long time?
  • What are the biggest pieces of advice that Jason would give to operators becoming investors?
  • What are the biggest mistakes that Jason made in his first 3 investments as a VC? How did he change?

4.) Mastering the World of Venture Today:

  • Why does Jason believe that he has become a worse investor with the rise of "remote investing"?
  • Why does Jason believe he is a worse investor without having a partner in SaaStr Fund?
  • Why does Jason believe that even the best founders do not want hard feedback anymore? Should we as VCs still give it to them? What has Jason learned here?
  • Will we see great LP churn and many LPs leaving the asset class? What will happen to the existing incumbents with massive AUM and reduced performance?

Nov 28, 2022

Miki Kuusi is the CEO of Wolt and Head of DoorDash International. In 2014 Miki founded Wolt with a mission to turn the smartphone into a remote controller for life, starting with delivering your favorite restaurant food, to you at home. Today Wolt operates in 23 countries, across several different categories, has over 4,000 employees, and last year, Doordash made the move to join forces with Wolt in a deal worth a reported $8.1BN. Previously, Miki was the CEO of Slush, one of the leading tech and investor events in the world attended by more than 25,000 people annually.

In Today's Discussion with Miki Kuusi:

1.) Founding Slush and Wolt: An Entry into Startups:

  • How did Miki come to found Wolt? What was that a-ha moment?
  • Did Wolt have product-market-fit from Day 1? What was the turning point when they did?
  • What does Miki know now that he wishes he had known when he started Wolt on Day 1?

2.) The Makings of a Truly Great Leader:

  • How does Miki define "high performance" today in leadership?
  • How does Miki think about what focus means in leadership? What is the hardest decision Miki has had to make when it comes to focusing the company? What did he learn from Ilkka @ Supercell?
  • What does Miki believe is the KPI of success as the CEO? How does it change?
  • What does Miki believe is the difference between good vs great leadership?
  • What does Miki believe is the biggest sacrifice he has made as the CEO?

3.) Hiring a Team to Compete on a Global Stage:

  • How does Miki use compensation to create a culture of ownership and accountability?
  • Does Miki start from a position of trust and it is there to be lost or no trust and it is there to be gained?
  • What is the difference between a team and a family in company building?
  • What is the core difference between trust and safety in company building? Why does Miki always want to have trust but not want to have safety?
  • What are the single biggest hiring mistakes that Miki has made? How has he learned from them?
  • Why does Miki believe you do not want to hire people that have done it before but hire the people who have seen those people do it before?
  • Why does Miki believe most companies are merely glorified recruiting operations?
  • Does Miki believe that companies need to be as big as they have grown into, headcount-wise?

4.) Miki Kuusi: The Personal Journey

  • What single day was the hardest day of the Wolt journey for Miki? How did it change him?
  • Why does Miki believe that for their Series B, all-bar one VC turned them down?
  • How does Miki assess his own relationship to risk and money today?
  • Why is Miki an advocate for founders taking secondaries along the journey?
  • What can Europe do to become a powerhouse in tech moving forward?
  • Why did Miki decide to sell the company to Doordash? What is he most excited to learn from Tony Xu, Doordash Founder and CEO?

Items Mentioned in Today's Episode:

Miki's Favourite Book: The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

Nov 25, 2022

Casey Winters is the Chief Product Officer at Eventbrite. Prior to Eventbrite, Casey led the growth product team at Pinterest. Before Pinterest, Casey started the marketing team at Grubhub and scaled Grubhub’s demand-side acquisition and retention strategies. 

Elena Verna is the Interim Head of Growth at Amplitude. Former exec @ Miro, Netlify, SurveyMonkey. Growth Advisor to companies including Krisp, MongoDB, Ledgy, and SimilarWeb.

Kieran Flanagan is SVP Marketing at HubSpot, where he has helped the business grow internationally, move to a product-led business, quadrupled its marketing demand, and built out its media team, including the acquisition of ‘The Hustle.’

Andy Johns career started in growth at Facebook when the company scaled from 100M-500M active users. Since he has worked in some of the leading growth orgs at companies like Twitter, Quora and more recently at Wealthfront as Head of Growth and President.

Bangaly Kaba is the Director of Product Management @ Youtube. Prior to Youtube, Bangaly led the product growth and consumer product orgs at Instacart and before Instacart was Head of Growth @ Instagram, helping grow Instagram from 440M to > 1B monthly actives in 2.5yrs.

Ed Baker is a growth advisor to various startups including Lime, Zwift, Whoop, Crimson Education, GoPeer, and Playbook. Ed was the VP of Product and Growth at Uber from 2013-2017. Prior to Uber, Ed was the Head of International Growth at Facebook.

Adam Fishman was the Chief Product and Growth Offer @ Imperfect Foods. Before Imperfect, Adam was VP of Product and Growth @ Patreon, Before Patreon, Adam was the Head of Growth @ Lyft, Adam was the first growth and marketing employee hired and grew the team to 18 people.

In Today's Discussion on When To Hire a Head of Growth:

1.) When is the right time to hear your first growth hire?

2.) Is this hire a senior growth leader or a more junior growth engineer?

3.) What can early-stage startups do to entice senior growth leaders to their early-stage company?

4.) What data infrastructure should be in place prior to hiring your first growth hire?

5.) What does the optimal onboarding process look like for all growth hires?

6.) What can founders and CEOs do to set their growth hires up for success?

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