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The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC takes you inside the world of Venture Capital, Startup Funding and The Pitch. Join our host, Harry Stebbings and discover how you can attain funding for your business by listening to what the most prominent investors are directly looking for in startups, providing easily actionable tips and tricks that can be put in place to increase your chances of getting funded. Although, you may not want to raise funding for a startup. The Twenty Minute VC also provides an instructional guide as to what it takes to get employed in the Venture Capital industry, with VCs giving specific advice on how to get noticed from the crowd and increasing your chances of employment. If that wasn't enough our amazing Venture Capitalists also provide their analysis of the current technology market, providing advice and suggestions on the latest investing trends and predictions. Join us so you can see how you can get BIG, powerful improvements, fast. Would you like to see more of The Twenty Minute VC, head on over to www.thetwentyminutevc.com for more information on the podcast, show notes, resources and a more detailed analysis of the technology and Venture Capital industry.
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Now displaying: Category: Investing
Feb 25, 2019

Frank Chen is a Partner @ Andreessen Horowitz, one of the world's most prestigious venture firms with a portfolio including the likes of Airbnb, Coinbase, Github, Lyft, Slack and many more incredible companies. As for Frank, prior to joining the world of venture, he was a VP of Products & UI Design at HP Software and before that held the same title at Opsware. Before that, even cooler, Frank was Director of Product Management @ Netscape where he led a cross-functional team that defined, shipped, and marketed Netscape's award-winning LDAP directory and security products. 

In Today’s Episode You Will Learn:

1.) How Frank made the move from the world of operations with Opsware and HP to being a Partner at Andreessen Horowitz?

2.) How does Frank view the current state of play for AI and machine learning? How does the rise of automation shift the economy as we know it? What does it do to class distinctions? How does Frank view it's impact on the labour market? How does Frank think about the value of truly large datasets? Where is the asymptotic moment where the utility value of data is realised?

3.) With the rise of self-driving, how does Frank perceive the future of car ownership? Who will fundamentally own and operate the vehicles? Will it be a horizontal play or a vertical play? In terms of adoption, why is Frank negative towards a driver assisted transition phase and believe in a more binary transition?

4.) How does Frank perceive the rise of automation and self-driving cars impacting public infrastructure? How will the layout of our cities change over time? How does Frank believe urban real estate could be optimised in a more efficient manner? Which nations does Frank believe will be the first to innovate here?

5.) What is the most challenging element of Frank's position as Partner @ a16z? How does Frank think about the right way to say not to an entrepreneur? How does Frank look to scale the learning curve rapidly when investigating new industries? What are the challenges here? What advice would Frank give to someone looking to scale learning curves?

Items Mentioned In Today’s Show:

Frank’s Fave Book: The Chronicles of NarniaThe Lord of The Rings

Frank’s Most Recent Investment: Branch

As always you can follow HarryThe Twenty Minute VC and Frank on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Feb 22, 2019

Rahul Vohra is the Founder and CEO @ Superhuman, the fastest email experience in the world. Fun fact, users get through their inbox twice as fast — and many see Inbox Zero for the first time in years! To date, they have raised funds from our friends at Boldstart, First Round, John Collison, Sam Altman, Wayne Chang, Mike Ghaffery and Yes VC just to name a few. Previously, Rahul founded Rapportive, the first Gmail plugin to scale to millions of users. Rapportive was ultimately acquired by LinkedIn.

In Today’s Episode You Will Learn:

1.) How did Rahul make his way into the world of startups with the founding of Rapportive and how did that transition to changing the world of email with Superhuman?

2.) What does Rahul mean when he says, "you can reverse engineer a process to get to product market fit"? What does Rahul believe is the defining metric which determines your "product market fit score"? What is Julie Supan's framework? How did Dropbox and Airbnb use it to increase their product market fit? How can founders implement it into their process?

3.) What can founders do to expand the customer base to include users that currently are "somewhat disappointed"? What are the right questions to ask? What do we do with this feedback? How do we further segment the user base? Why should we "disregard the users whereby the primary benefit of the product does not resonate"? 

4.) How does Rahul approach product roadmap and prioritisation? How can founders ensure that continuous tracking and user feedback is engrained within the organisation? What tools does Rahul do to monitor and capture this? What are some of Rahul's biggest lessons from going through this painstaking process stage by stage? 

5.) Finally on fundraising, what does Rahul mean when he says, "always be raising but never be actively raising"? What are the benefits of this? How can founders transition catch up coffee into fundraising subtly? How does Rahul feel about party rounds? What are the pros? What are the downsides? How does Rahul advise founders here?

Items Mentioned In Today’s Show:

Rahul’s Fave Book: The Art of Game Design

As always you can follow HarryThe Twenty Minute VC and Rahul on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Feb 18, 2019

Steve Case is Chairman and CEO of Revolution with the mission being to establish themselves as the premier venture firm outside of Silicon Valley. On the other side of the table, Steve is recognised as one of America’s best-known and most accomplished entrepreneurs as the co-founder of America Online (AOL). Under his leadership, AOL was the first internet company to go public and became the world’s largest and most valuable internet company delivering an 11,616% return to shareholders. In 2000, Steve negotiated the largest merger in business history, bringing together AOL and Time Warner. Among many other achievements, in 2014, Steve was named a Presidential Ambassador for Global Entrepreneurship. Steve has also been a leading voice in shaping government policy and was instrumental in passing the JOBS (Jumpstart Our Business Startups) Act. Finally, Steve is also Chairman of the Case Foundation, where he and his wife, Jean, have invested in hundreds of organizations, initiatives and partnerships.

In Today’s Episode You Will Learn:

1.) How Steve made his way into the world of technology with the founding of AOL in 1985 and how that led to his founding of Revolution and investing today in the "rise of the rest" today?

2.) Having sat on both sides of the table both as founder and VC, what does Steve thinks make the truly special VCs? How do they engage with entrepreneurs? How do they actively move the needle for their companies? How would he like to see VCs of the future change and adapt their ways?

3.) How does Steve think about market timing when investing today? What were some of Steve's biggest lessons from seeing the dot com bubble and 2008 in both the role of entrepreneur and investor? What does he mean when he says, 'it can be dangerous to have a depression mentality' when investing?

4.) How does Steve analyse and assess the current fundraising environment today? Why does Steve see an incredible opportunity in funding companies outside the 3 traditional hubs of Silicon Valley, NYC and Boston? What needs to happen to drive this equalisation of funding further? What would Steve like to see change?

5.) What does Steve think are the 3 seminal roles of the CEO? What does Steve mean when he says that the CEO 'must be a shock absorber for company morale'? How does Steve deal with s*** hit the fan moments? What are his coping mechanisms and how does he advise entrepreneurs on them?

Items Mentioned In Today’s Show:

Steve’s Fave Book: The Third WaveBe Fearless: 5 Principles For A Life of Breakthroughs and Purpose

As always you can follow HarryThe Twenty Minute VC and Steve on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Feb 15, 2019

Henrique Dubugas is the Founder & CEO @ Brex, the first corporate card for startups offering instant online application, no personal liability, and tailored rewards. In a staggering 2 years, Henrique has grown Brex to a $1.1Bn valuation having raised over $180m in funding from some of the best in the business including Peter Thiel, Max Levchin, Elad Gil, DST, Y Combinator and IVP just to name a few. As for Henrique, prior to founding Brex he founded Pagar.me, a payments solution that he sold in Sept 2016, a year that the platform processed over $1.5 billion in GMV.

In Today’s Episode You Will Learn:

1.) How Henrique made his way from learning to code games in Brazil to starting a leading payment processor to founding one of the world's fastest growing B2B companies in Brex?

2.) How does Henrique think about hiring the very best people? How has that strategy shifted and changed over time? What is the best advice Henrique has been given on hiring? What interview questions does Henrique think are crucial to ask? What are leading indicators that an individual has the ability to scale with the company?

3.) Why does Henrique think it is wrong to down people for being "compensation motivated"? How does Henrique think about compensation structures? Should candidates have to take pay cuts to join startups? What have been some of Henrique's biggest learnings and challenges here?

4.) How does Henrique approach the current sentiment to fundraising in the valley today? Why does Henrique disagree with founders who have periods of not speaking to VCs? What does Henrique believe is the right way to build VC relationships? How does Henrique think about the right time to raise? What advice does Henrique have for founders when it comes to investor selection?

5.) How does Henrique think about his own personal development? Where would he personally like to improve and strengthen? What is he doing to make this happen? How has Henrique seen himself as CEO change over the last 2 years with Brex? What have been some of the challenges of scaling himself as CEO?

Items Mentioned In Today’s Show:

Henrique’s Fave Book: 7 Powers: The Foundations of Business Strategy

As always you can follow HarryThe Twenty Minute VC and Henrique on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Feb 11, 2019

David Cohen is the Founder and co-CEO of Techstars, the worldwide network that helps entrepreneurs succeed. To date, David has backed hundreds of startups including the likes of Uber, SendGrid, Twilio, ClassPass, PillPack and more. In total, these investments have gone on to create more than $80B in value. Prior to Techstars, David was a co-founder of Pinpoint Technologies which was acquired by ZOLL Medical Corporation in 1999. Later, David was the founder and CEO of earFeeder, a music service that was sold to SonicSwap. If that was not enough, David is also theco-author (with Brad Feld) of Do More Faster; Techstars Lessons to Accelerate Your Startup.

In Today’s Episode You Will Learn:

1.) How David made his way from, his words "geeky hacker" to the founder of one of the world's largest accelerators, Techstars and investor in multiple unicorns?

2.) What does David mean when he says that when assessing founders he studies "the moment of integrity"? What does he want to see from founders in those moments? What are some potential red flags? If a negative response, what are the subsequent actions an investor must take in this situation?

3.) How does David think about the right time to establish a board? What are the benefits of establishing your board with the seed round? What does David believe is the key to highly efficient boards? How has David changed as a board member over the years? Why does David believe, when building a company, "you always have to have a pessimist in the room"?

4.) When negotiating deals, what does David mean when he says "the terms must match the story"? How does David determine between a bridge and a bridge to nowhere? What can investors do to protect themselves if the targets of the business are not met and they have an uncapped note in place? How should they communicate this?

5.) Techstars today invests in over 500 companies per year, how does David think about reserve allocation across the portfolio? How does David feel about stack ranking portfolio co's quarterly and concentrating capital accordingly? Why is this not effective? Why should seed and angel investing be an entirely different asset class to VC?

Items Mentioned In Today’s Show:

David’s Fave Book: The Soul of Money: Transforming Your Relationship with Money and Life

David’s Most Recent Investment: Ordermark

As always you can follow HarryThe Twenty Minute VC and David on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Feb 8, 2019

Anjney Midha is the Founder & CEO @ Ubiquity6, the startup that allows you to edit reality together, turning any location into a space for real-time, shared AR and VR experiences. To date, Anjney has raised over $38m in funding for Ubiquity6 from some of the very best in the business including Phin @ First Round, Mike Volpi @ Index and Mitch @ Benchmark. Prior to Ubiquity6, Anjney spent 4 years on the other side of the table as an investor @ Kleiner Perkins and then as Founding Partner @ KPCB Edge, Kleiner's program helping founders get off the ground in AR, VR and Computer Vision.

In Today’s Episode You Will Learn:

1.) How Anjney made his way into the world of startups on the investing side of the table with Kleiner Perkins and how that transitioned to his founding of Ubiquity6?

2.) What does Anjney believe is structurally wrong with venture now more than ever? How does the extended period of privatisation affect emerging partners in venture firms? How does Anjney think the very best of investors think about and analyse history? Why does Anjney believe venture is the business of financing "creative hits"?

3.) What are the 3 structural impediments facing venture today? Why and how does Anjney believe we will see a new class of VC enter the space and be very successful? In what form could this take? How can they outcompete the current crop of VCs? What does Anjney mean when he discusses the "squishy middle" of VC?

4.) Anjney is backed by Index, Benchmark and First Round, what are the commonalities among those firms that make them so special? How do the very best of firms engage and build relationships with their entrepreneurs? How does Anjney believe that focus can be successfully applied to venture? What is the right way for VCs to evaluate themselves?

5.) What do VCs really want to know when they are approaching risk assessment with founders? What can founders do to mitigate risk when pitching to VCs? How do the very best founders attract the very best talent to their team? What are the commonalities? Where do some go wrong in building the optimal team?

Items Mentioned In Today’s Show:

Anjney’s Fave Book: Rainbows End

As always you can follow HarryThe Twenty Minute VC and Anjney on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Feb 4, 2019

Sam Lessin is a Founding Partner @ Slow Ventures, one of the leading early-stage funds on the West Coast with a portfolio including the likes of Robinhood, Gusto, Pinterest, Casper, Postmates and many more incredible companies. Sam is also the Co-Founder & Co-CEO @ Fin Analytics, the startup that provides precision measurement and coaching for high-performance operations teams. Before founding Fin and Slow, Sam spent 4 years at Facebook as a VP of Product Management following their acquisition of his prior company, Drop.io.

In Today’s Episode You Will Learn:

1.) How Sam made his way into the world of venture with the founding of Slow following the acquisition of his company and 4 years in product at Facebook?

2.) How does Sam think about the difference between investing small personal checks vs managing institutional funds? What is the subsequent effect on mindset when investing? How does one prevent an increased conservatism? What does Sam mean when he says "VC forces some businesses into existence and makes others hard to fund?

3.) Why does Sam believe that man + machine must have a symbiotic relationship in the future? What does this look like in reality? When comparing today to the industrial revolution, is Sam concerned by the increased rate of adoption today? What does this mean for different categories of work? Why does Sam believe we will need more philosophers?

4.) Why does Sam believe that too much emphasis in the world of crypto is placed on Dapps? Why is he concerned by Dapps? What are of crypto does Sam believe is most exciting and investable today? Does Sam agree with Elad Gil that we will see the re-centralisation of talent back to the valley with the scaling of crypto co's?

5.) On governments, why does Sam not believe that both local and national governments will allow scooter companies to become meaningfully profitable in the future? How does Sam think about the balance and trade-off between privacy and security that faces many governments today?

Items Mentioned In Today’s Show:

Sam’s Fave Book: Lessons of History

Sam’s Most Recent Investment: Fetcher.ai

As always you can follow HarryThe Twenty Minute VC and Sam on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Feb 1, 2019

Joel Flory is the Founder & CEO @ VSCO, the startup that allows you to take your photography to the next level, with the mission to help everybody fall in love with their own creativity. To date, Joel has raised over $70m in funding with VSCO from some of the best in the business including Accel, Glynn Capital Management and Goldcrest Investments. Prior to founding VSCO, Joel founded his own photography company which he ran successfully for 10 years.

In Today’s Episode You Will Learn:

1.) How Joel made his way from photographer to one of San Francisco's hottest startup founders today?

2.) How does Joel approach the current sentiment and approach to fundraising? Why were Joel and his co-founder unable to raise in the early days? How does Joel approach the element of investor selection? Brand name or partner? How does Joel look to really build relationships with VCs in compressed timeframes? What is Joel's litmus test to determine if a VC is interested? What single value add can a VC provide that is most important?

3.) What does Joel mean when he says, "you have to align your business model with your mission?" How can one really determine if they are aligned? How does this alignment change and alter with scale? What was the thinking behind the shift to a subscription business with VSCO? Was Joel worried it would impact the valuation and change the valuation mechanism to a multiple of revenue assessment?

4.) What do the optimal leadership team dynamics look like to Joel? What has worked well for Joel in binding the leadership team together? What have been some of the biggest challenges? How does Joel think about cross-functional communication across the leadership team?

5.) How does Joel think about his personal development today? Where would he like to improve? Where is he already strong? With a family and company in hyper-growth, how does Joel think about attaining that work-life balance? What advice would he have for other here? How does Joel determine what to say yes vs no to? What are some tips and hacks to this?

Items Mentioned In Today’s Show:

Joel’s Fave Book: How To Talk So Kids Will Listen and Listen So Kids Will Talk 

As always you can follow HarryThe Twenty Minute VC and Joel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.


Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Jan 28, 2019

Josh Kopelman is Founder & Partner @ First Round, one of the world’s leading seed funds with a portfolio including the likes of Uber, Warby Parker, Flatiron Health, Square, HotelTonight, GOAT and more incredible companies. As for Josh, he founded First Round in 2004 to reinvent seed stage investing. Since he has invested in over 200 startups and been ranked 4th in Forbes Midas List and named one of the top ten ‘angel investors’ in the US by Newsweek magazine. Josh has previously sat on the boards of Flatiron Health, Clover Health, AppNexus and more. 

In Today’s Episode You Will Learn:

1.) How Josh made his way into the wonderful world of venture from angel investing and what the inspiration behind the founding of First Round was?

2.) How does Josh think about price sensitivity today? What were his learnings from being priced out of the seed round for Twitter and Dropbox? How has Josh seen his relationship to price change over time? How did witnessing the boom and bust both as operator and investor affect his investing mentality today?

3.) How does Josh and First Round think about reserve allocation? How has their thinking changed and evolved over time? Does Josh believe that ownership is fundamentally built on first check? What does the investment decision-making process look like for reserves? In terms of allocation, how does Josh think about time allocation across portfolio? Spend it with the winners, they return the fund or the strugglers and save cents on the dollar?

4.) Josh has spent over 3,000 hours on boards, what have been some of the biggest inflection points that have changed the way he thinks about being a good board member? How has he seen his style and approach change over time? What advice would Josh give to an individual that has just gained their first institutional board seat?

5.) Why does Josh believe that we fundamentally neglect "the pick" today in startup world? Why does Josh believe a high degree of startup mortality begins at the pick (idea) stage? How do the very best founders aproach this stage? How should these founders approach picking their investors? What should they look for? What should they be wary of?

6.) Why does Josh want to be known as a better picker of partners than investments? How has Josh thought about the building ou of the first round partnership over time? If there was anything he would have done differently, what would it be? Why does Josh fundamentally disagree with attribution? How does Josh think about generational transition? What are the steps required to do it well?

Items Mentioned In Today’s Show:

Josh’s Fave Book: Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts

As always you can follow HarryThe Twenty Minute VC and Joel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.


Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Jan 25, 2019

Olof Mathé is the Founder & CEO @ Mixmax, the startup that provides powerful analytics, automation and enhancements for your outbound communications. In the past, Mixmax achieved the almost the impossible in SaaS, true viral growth and a $0 CAC. As a result, Olof has raised over $13m in funding from some dear friends of the show in the form of Jason @ SaaStr, Mike @ Harrison Metal, Mike @ Floodgate and Carl @ Creandum, to name a few. As for Olof, prior to Mixmax he led the team that built Inkling Habitat, now adopted by the world’s largest publishers and before that he was an entrepreneur and worked at Skype and McKinsey.

In Today’s Episode You Will Learn:

1.) How Olof made his way from the world of McKinsey and Skype to changing the way we interact with our email today with Mixmax?

2.) What does Olof mean when he says that founders go through 3 stages of denial when scaling their team? How does Olof think about the right time to add certain roles? What have been some of his big learnings here? Where do people make mistakes in the timing of hires? How does Olof think about the transition from generalist to specialist with scale?

3.) Why does Olof believe that in the majority of cases, it is not optimal or possible for founders to hire through their network? What is the right way for founders to approach building candidate pipe? What is the right way for founders to engage with recruiters? What is required in the recruiter/founder relationship for it to be a success?

4.) Why does Olof get worried when he hears "they will grow into the role"? What are the core leading indicators that suggest someone has the ability to scale vs not scale with the role? How much time does one give an employee to provide value and show their ability in the team? How does Olof think about the right way to let someone go?

5.) What are the 3 interview questions that all founders must ask in the hiring process? What answers indicate a candidate that is best suited for the role and company? What are red flags to watch for both in their answer and tone? How has Olof changed his hiring style over the last few years with Mixmax?

Items Mentioned In Today’s Show:

Olof’s Fave Book: SPQR: A History of Ancient Rome

As always you can follow HarryThe Twenty Minute VC and Olof on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.


Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Jan 21, 2019

Hunter Somerville is a Partner at Greenspring Associates, a leading venture firm and fund of funds. On the direct side their portfolio includes the likes of Sonos, App Annie, Docusign and Alibaba just to name a few. As for their fund investing, they have backed the likes of Accel, Founders Fund, Thrive, Lightspeed, Foundry Group and many more incredible managers. As for Hunter, he is actively involved in the assessment of micro-vc managers for the Firm where he sits on the LP advisory boards for the likes of Pear, Foundry Group, Scale Venture Partners and BullPen Capital just to name a few. Prior to joining Greenspring, Hunter worked as an Associate for Camden Private Capital.

In Today’s Episode You Will Learn:

1.) How Hunter made his way into the world of fund investing and came to be a Partner @ Greenspring?

2.) How does Hunter assess the world of micro-VC today? Does Hunter think we will see the market start to shrink as LPs become over-allocated to the space? Why does Hunter believe the barriers for micro VCs to raise are lower than ever? What does this mean for the future of early stage?

3.) How does Hunter fundamentally approach the assessment of new funds? Is it all about track record? How does he look to build a framework/model to predict future performance? What makes Hunter sceptical when assessing new opportunities? Where do many managers go wrong in the fundraising process? How does Hunter think about loss ratio?

4.) As an LP having to allocate to multiple different stages, why does Hunter feel there is a shortage of dedicated A and B round funds? How does Hunter expect both reserve allocation and loss ration to alter as we move from early to later stage? How does Hunter feel about opportunity funds? How does Hunter and other LPs assess GP led restructurings?

5.) Why is Hunter bullish on the future for direct secondaries? Why does he believe this is fundamentally good for the ecosystem? How does Hunter think about early stage managers in their needs for early liquidity? To what extent will early stage managers need to navigate the private secondaries market to attain this liquidity?

Items Mentioned In Today’s Show:

Hunter’s Fave Book: Great Expectations by Charles Dickens

Hunter’s Most Recent Investment: Amplify Partners

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder. Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.


Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Jan 18, 2019

Assaf Wand is the Founder & CEO @ Hippo, a new kind of insurance company that provides smart coverage for homeowners with a quote in just 60 seconds. To date, Assaf has raised over $109m in funding for Hippo from some dear friends of the show in the form of Felicis Ventures, GGV Capital, Fifth Wall, Zeev Ventures and Lennar just to name a few. Prior to re-imagining the world of insurance, Assaf founded Sabi, creating products that improve everyday life with superior functionality and design. Sabi was acquired by Urbio in 2015. Before that Assaf held numerous different roles including as a consultant at McKinsey and Investment Associate at Intel Capital.

In Today’s Episode You Will Learn:

1.) How did Assaf being the worst employee in the world lead to his entrance into the world of early-stage startups and the founding of Hippo?

2.) How does Assaf analyse the current sentiment and approach to fundraising in the valley today? Why does Assaf believe that every company looks one round earlier than it should be for the VCs? How does Assaf think about investor selection? What is the single biggest value a VC partner can provide? Does Assaf agree that founders should "always be raising"? Why does Assaf believe that top funds should not get significant discounts?

3.) What does Assaf believe are the biggest mistakes entrepreneurs make when building their board? On boards, why does Assaf believe there is a danger that partners from top funds have their ideas overweighted due to the prestige of their fund? What can be done to prevent this? What does Assaf believe is the right screening process for new board members?

4.) What does Assaf believe separates the good from the great when it comes to board members? How does Assaf really look to building meaninful relationships with his board members? What has worked well? On the flip side, why does Assaf believe the No 1 element of a board is "do no harm"? Where can board members actually be damaging?

5.) Hippo is growing 30% MoM and will be in 80% of the US in the next 12 months, how does Assaf think about when is the right time to put the pedal to the metal? What are those leading indicators? Where do many founders go wrong here? Is it simply a case of whenunit economics work, one is ready to scale?

Items Mentioned In Today’s Show:

Assaf’s Fave Book: The FountainheadThe Pillars of The Earth

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder. Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.


Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Jan 15, 2019

Fred Destin is a Founding Partner @ Stride.VC, one of Europe's newest seed funds with a portfolio including the likes of Cazoo and Forward Health. Over his 17 year career in venture, Fred has established himself as one of Europe's leading VCs with the exit value of 3 of his portfolio companies alone last year totalling more than $4.5Bn with PillPack's $1Bn sale to Amazon, Zoopla to Silverlake for $3Bn and Integral Ad Science to Vista for $850m. Fred has also led investments as a General Partner @ Accel in Deliveroo, the world leader of food on demand and Carwow, the number 1 for new car sales in the UK.

In Today’s Episode You Will Learn:

1.) How Fred made his way into the world of venture and early stage? What was behind his decision to leave Accel to found Stride with Harry?

2.) Why does Fred think many today misunderstand "risk" in venture? How does that apply across the portfolio? Does Fred agree with Brian Singerman, "venture is a game of upside maximisation"? What risks does Fred define as acceptable vs non-acceptable risks? How does Fred really look to strength test the quality and depth of a founder pre-investment? What are the benefits of going through conflict early?

3.) How does Fred think about price sensitivity? What are the core questions a VC can ask when considering the pricing of an opportunity? How does Fred think about reserve allocation? How does Fred analogize this to the best traders? To what extent does TAM play a dominant role in Fred's evaluation? What does Fred mean when he says "we have to remember, we are the ones that get picked also"?

4.) How does Fred think about and assess innovation within venture? How does Fred perceive the role of data to impact venture over the coming years? Why does Fred believe it is exaggerated that data will disrupt the early stage in the coming years? Where would Fred like to see further innovation in the mechanics of venture?

5.) What does Fred believes separates the good from the great when it comes to board members? How can board members create an environment where the entrepreneur feels they can say all that is wrong? Where do many board members go wrong? Why are board members so wrong to bash a founder for missing their numbers? Why does Fred believe that plans are fiction? WHy is the framework of the plan what really matters?

Items Mentioned In Today’s Show:

Fred’s Fave Book: Man's Search for Meaning

As always you can follow HarryThe Twenty Minute VC and Fred on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you thinking about life insurance in the new year? Ladder. Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY.

Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Jan 11, 2019

Avi Meir is the Founder & CEO @ TravelPerk, the startup that allows you to book, manage and report all your business travel in one place. To date, Avi has raised over $73m with TravelPerk from the likes of Felix Capital, Yuri Milner, Spark Capital, Sunstone and LocalGlobe to name a few. Before founding TravelPerk, Avi founded HotelNinjas, a web-based hotel management software platform that was ultimately acquired by Booking.com. Prior to that, Avi was VP Product at Budgetplaces.com, which was acquired by Palamon in 2011.

In Today’s Episode You Will Learn:

1.) How Avi made his way from the world of hotels to the world of founding startups and what was his entry point? How did Avi's experience with HotelNinja's impact his operating mindset with TravelPerk today?

2.) How does Avi think about attaining the right board composition? What is the ideal structure? How important is it to have industrial experience around the table? What are the 2 other core skills that Avi believes are required on the board? What can founders do to ensure plasticity of mindset at a board level?

3.) What makes the truly special board members? What do they do both in the good and the bad times to make them so good? What does Avi believe makes the more challenging board members to work with? Why does Avi believe that culture fit at the board level is not discussed enough? What can be done by the founder to improve this?

4.) TravelPerk has now raised over $75m in funding, what does Avi believe they have done well to date to allow them to raise this? For the next round, what would Avi like to improve upon and pushback on further? What advice does Avi have for founders entering negotiations when it comes to both valuation and option pool?

5.) Why does Avi believe that culture and growth are 2 sides of the same coin? What have been some of the biggest challenges in scaling the team with the scaling of the company? How does one retain startup culture when no longer a startup? What would Avi do differently with regards to expansion with the benefit of hindsight?

Items Mentioned In Today’s Show:

Avi’s Fave Book: Delivering Happiness: A Path to Profits, Passion and Purpose

As always you can follow HarryThe Twenty Minute VC and Avi on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jan 7, 2019

Scott Belsky is an executive, entrepreneur, author, and investor. He currently serves as Adobe's Chief Product Officer and Executive Vice President, Creative Cloud. Before Adobe, Scott co-founded Behance in 2006 and served as CEO until Adobe acquired Behance in 2012. Alongside his role at Adobe, Scott is a Venture Partner at one of the world's leading venture firms, Benchmark. Scott also actively advises and invests in startups personally having one of the most incredible angel portfolios with early checks in Pinterest, Uber, Periscope, Warby Parker, Carta, Flexport and more. Scott is also the author of Harry's favourite book of 2018, The Messy Middle.

In Today’s Episode You Will Learn:

1.) How Scott made his way into the world of startups with Behance, how that translated to the world of angel investing and being Chief Product Officer @ Adobe? WHat does Scott mean when he discusses the correlation between utilisation and happiness?

2.) What does Scott mean when he says he looks for people whereby 'conversations improve by step function?" What are the best examples of this? How have they shown this? How does Scott think startups founders can manufacture motivation? How has Scott seen the best founders hire the very best team? How do the best founders determine between a stretch and a stretch too far?

3.) In terms of product, what does Scott mean when he refers to the "value of slow cooking"? How does that relate to product creation? Why does Scott often have issues with the MVP approach seen today? How does Scott think about the importance of product simplicity? How can one maintain that over time? Why does Scott believe more founders should spend more time crafting the last mile user experience than they do?

4.) Simplicity is great but VCs often suggest, non-defensible, how does Scott think about building defensibility with simplicity? Simplicity often also narrows market size, how does Scott think about and analyse market size today when investing? Where does Scott think many investors go wrong today when trying to measure market size?

5.) What does Scott mean when he says "resources are like carbs, resourcefulness is muscle"? Why does Scott believe we need to challenge our faith in the strength of resources? What advice does Scott given when founders ask, "when is the right time to raise big"? How has Scott's writing of the book influenced his mindset when engaging with founders today and investing?

Items Mentioned In Today’s Show:

Scott’s Fave Book: Endurance: Shackleton's Incredible Voyage to the Antarctic

Scott’s Most Recent Investment: Assembled Brands

As always you can follow HarryThe Twenty Minute VC and Scott on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dec 28, 2018

Andrew Dudum is the Founder & CEO @ Himsone of the fastest growing consumer brands of our time and the fastest growing men’s health and wellness brand. To date, they have raised over $97m in VC funding from some of the best in the business including Thrive, Founders Fund, Forerunner, IVP, Redpoint and SV Angel just to name a few. Andrew is also Venture Partner at Atomic, a venture-builder backed by Peter Thiel, Marc Andreesen and many of the world’s best investors who recently announced their new $150m fund to start companies solving the world’s problems. Prior to Atomic and Hims, Andrew led Product at TokBox.com, the leader in web-based communication and In 2012 TokBox was acquired by the global telecommunications company Telefonica ($TEF).

In Today’s Episode You Will Learn:

1.) How Andrew made his way into the world of startups, came to build a venture builder backed by Thiel and Andreesen before starting the fastest growing men’s health and wellness brand in Hims?

2.) How does Andrew view the world of online and offline marketing in today’s proliferated D2C space? What were the core elements that allowed Hims to achieve such success with their branding? How does Andrew respond to suggestions that there is a lack of free and open distribution due to incumbents paying up for traditional channels making CAC unachievable for startups? How does Andrew look to solve for this?

3.) What does Andrew believe it is that has allowed Hims to execute faster than any other D2C brand in history? How does Andrew distinguish between people and process when considering the scaling at different stages of the business? What are the pros and cons of having such constraints on headcount? When is the right time to pour fuel on the fire?

4.) Hims raised their last round at a $200m valuation in less than a year of operating, how did Andrew evaluate this one? Does this not effectively price Hims out of the majority of M&A?  What leads Andrew’s thesis with his suggestion that he thought the valuation was “quite frankly, a great price for investors”? What advice would Andrew have for founders entering the fundraising process?

5.) Andrew is also the co-founder @ Atomic, so what really is a venture builder? How have Atomic built a framework around idea generation? How do Atomic determine which ideas to pursue and which to disregard? How does data and benchmarking play a central role in this process?

Items Mentioned In Today’s Show:

Andrew’s Fave Book: Creativity Inc

As always you can follow HarryThe Twenty Minute VC and Andrew on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Much like how Carta changed how private companies manage their cap tables and 409A valuations, Carta are now doing the same for fund administration. With Carta’s new, modern fund administration software and services, you get a real-time dashboard of your general ledger, can securely share info with your LPs, and issue capital calls–from the same platform, you accept securities and request cap table access. So essentially, Carta simplifies how startups and investors manage equity, fund administration, and valuations. Go to carta.com/20VC to get 10% off.

Dec 17, 2018

Ted Wang is a Partner @ Cowboy Ventures, one of Silicon Valley's leading early-stage funds with the likes of Philz Coffee, Dollar Shave Club, Brandless, DocSend, Accompany and Brit + Co all in their portfolio. As for Ted, prior to VC, Ted spent X years as a leading Silicon Valley lawyer with Fenwick & West where he worked with some of the most notable companies of our times including Facebook, Dropbox, Twitter, Square and Spotify just to name a few. Ted also created the Series Seed Documents - a set of open-sourced financing documents posted on Github used by thousands around the world today.

In Today’s Episode You Will Learn:

1.) How Ted made his way from one of the most renowned lawyers in the valley with Fenwick & West to partner @ Cowboy alongside Aileen Lee?

2.) How does Ted fundamentally approach risk today? Given this mindset, how does this impact Ted's thinking on optimizing portfolio construction? On the flip side, how has Ted seen many founders wrongly approach the theme of risk? What is the question they need to be asking? What is Ted's story about risk related to his time working with Jet?

3.) What is it that makes Ted believe that "advice is often oversimplified"? If so, how can VCs provide tangible advice to their portfolio companies today? How can founders determine what is the right advice to accept and integrate vs listen and disregard? How does this lead Ted's thinking on the 2 core value adds a VC can provide? What advice did Dropbox Founder, Drew Houston give Ted on when to accept advice?

4.) What does Ted mean when he says "there are 4 parts to venture"? How does Ted think about the theme of learning and self-improvement when assessing founders? How does he look to do this pre-investment? What questions reveal the most? Applying it to himself, where will Ted place his biggest efforts on learning within the realm of venture over the next 12 months?

Items Mentioned In Today’s Show:

Ted’s Fave Book: 7 Habits of Highly Effective People

Ted’s Most Recent Investment: Fullcast

As always you can follow HarryThe Twenty Minute VC and Ted on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Much like how Carta changed how private companies manage their cap tables and 409A valuations, Carta are now doing the same for fund administration. With Carta’s new, modern fund administration software and services, you get a real-time dashboard of your general ledger, can securely share info with your LPs, and issue capital calls–from the same platform, you accept securities and request cap table access. So essentially, Carta simplifies how startups and investors manage equity, fund administration, and valuations. Go to carta.com/20VC to get 10% off.

Dec 14, 2018

Dave Vasen is the Founder & CEO @ Brightwheel, the child management software solution you need and now the #1 platform for early education. To date, with Brightwheel, Dave has raised over $33m in funding from some of the best in the business including Bessemer, GGV Capital, Lowercase Capital, Chan Zuckerberg Initiative, our friends at Eniac Ventures and then the likes of Mark Cuban and Chris Sacca. As for Dave, prior to Brightwheel, he was a VP of Product @ AltSchool and before that spent 3 years at Amazon in numerous different roles including Head of K-12 Education on Kindle and developed and launched the “Made for Kindle” licensing program – both domestic and global.

In Today’s Episode You Will Learn:

1.) How Dave made his way into the world of edtech and startups from being a consultant at Bain and product manager at Amazon?

2.) Why does Dave fundamentally disagree that founders should always be raising? What is the right way that founders should approach the fundraise? How can founders turn down investor meetings politely when requested and they are not raising? What is the right way to think about capital as a weapon today and the effective allocation of it?

3.) Why does Dave disagree with many elements that the Founder/VC relationship is a marriage? What one element, other than capital, does Dave most look for in a potential investor? What can founders do to really compress the fundraise timeline? How can founders build relationships with VCs under these compressed conditions?

4.) In the valley there is a large amount of glorification around the scaling and founding of companies, how does Dave feel personally about this glorification? How would Dave like to see this mindset fundamentally change? In terms of mindsets, why does Dave push back against the suggestion of VC "pattern recognition"? How has being an older founder and father changed the way he thinks about building Brightwheel today?

5.) How does Dave interpret the meaning of focus today with regards to company building? How does Dave determine the elements to really double down on? How does Dave think about saying no to opportunities? What framework does he use? What have been some of Dave's biggest learnings on culture and being prescriptive around it?

Items Mentioned In Today’s Show:

Dave’s Fave Book: The Five Dysfunctions of a Team: A Leadership Fable

As always you can follow HarryThe Twenty Minute VC and Dave on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dec 10, 2018

Anu Duggal is the Founding Partner @ Female Founders Fund, a leading early-stage fund investing in female-founded technology companies. Within their incredible portfolio is the likes of Zola, Rent The Runway, Maven Clinic, Tala and previous guest, Rockets of Awesome. They also have the most incredible mentor network including the founders of Stitchfix, Care.com, Zola and Tala. Prior to founding Female Founders Fund Anu was CEO @ Doonya, a dance fitness and media company inspired by Bollywood and fun fitness. Before that, Anu was Founder @ Exclusively.In where she headed up New Business Development.

In Today’s Episode You Will Learn:

1.) How Anu made her way into the world of VC with her founding of Female Founders Fund?

2.) What does Anu mean when she says she likes to focus on "non-obvious opportunities"? What are some clear examples of this? These non-obvious opportunities often appear to have smaller markets, how does Anu think about market size and evolution when investing? Can one blame male VCs for sometimes not identifying with the problem set being solved? What can be done to solve this problem?

3.) What 3 elements do Anu most look for when investing in consumer today? How does Anu respond to the statement that consumer may produce healthy revenue but at the end of the day they will never really produce venture return and be sold for 1.6x EBITDA? How does Anu assess the state of the M&A market today in the world of CPGs?

4.) How was the first fundraising for Female Founders Fund? What did the process look like in terms of amount of meetings, total committed LPs and duration spent raising? What were the common pushbacks from LPs in the fundraise? What did Anu do well that she would do again? How did the raise of the 2nd fund compare to the raise of Fund I?

5.) What does Anu mean when she states, "the power of the female network"? How has Anu seen this work in the real world? How does this allow Anu to see the best deals? How does Anu think about scaling check size and ownership with fund II? How does Anu think about reserve allocation when re-investing?

Items Mentioned In Today’s Show:

Anu’s Fave Book: Educated: The international bestselling memoir

Anu’s Most Recent Investment: Co-Star, Hyper-Personalized, Real Time Horoscopes

As always you can follow HarryThe Twenty Minute VC and Anu on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Nov 30, 2018

Tom Blomfield is the Founder & CEO @ Monzo, in it's simplest words, the bank of the future allowing you to open a full UK bank account in minutes, from your phone. To date, Tom has raised over $190m in funding for Monzo from the likes of Thrive, Accel, General Catalyst, Stripe, Mike Moritz and Goodwater just to name a few. As for Tom, prior to Monzo he was the Co-Founder of another of London's rocketship startups in the form of GoCardless and before that co-founded student marketplace Boso.com alongside Triplebyte Founder, Harj Taggar.

In Today’s Episode You Will Learn:

1.) How Tom made his way into the world of startups from University and came to found the bank of the future in Monzo?

2.) Why does Tom believe that scaling a company today can really be broken up into 3 distinct phases? What are those phases? How does what one needs for each phase differ accordingly? What elements has Tom found most challenging to navigate in the scale-up phase? Are there challenges or elements that are the same across every company?

3.) Why does Tom believe that product decision-making is both an art and a science? How does Tom determine when is the right time to add ancillary products? How can one really stress-test true customer love for the first product? How does Tom balance between product expansion vs geographical expansion? How does Tom balance between being customer-driven vs customer informed?

4.) Tom has grown Monzo to 1.2m users with virtually no advertising, how does Tom respond to the statement that there is a lack of free and open distribution today? What does Tom mean when he says "when it comes to customer acquisition you have to play a different game"? In building community, what have Monzo done so right? Where have they made mistakes? What have been some big lessons on early community building?

5.) Having raised over $190m in VC funding, what have been some of Tom's biggest lessons when it comes to fundraising? Why does Tom believe that so few boards are managed and run well? Where do they go wrong? What do great board managers do to run an efficient process? What does Tom mean when he says "use board meetings as a tool to instil operational excellence?"

Items Mentioned In Today’s Show:

Tom’s Fave Book: The Hard Thing About Hard Things by Ben Horowitz

As always you can follow HarryThe Twenty Minute VC and Tom on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Nov 19, 2018

Jeff Morris Jr is the Founder of Chapter One, an early stage seed fund investing in blockchain assets, mobile and subscription businesses. Chapter One's Portfolio includes the likes of Lyft, Brandable, Crypto Kitties and many more incredible companies. However, Jeff is unique as Chapter One is only one of his hats, Jeff is also the Director of Product & Revenue @ Tinder and when asked to lead the revenue team they were ranked #17 in the app store. Within a year, under Jeff's leadership, Tinder became the #1 top grossing app in the world.

In Today’s Episode You Will Learn:

1.) How Jeff made his way into the world of startups and angel investing, how that lead to his role as Director of Product and Revenue @ Tinder and a leading early-stage investor with Chapter One?

2.) Jeff has previously said, "apply an investor mindset to every product decision I make". What are the foundational questions involved? What are the inherent challenges of being so deep in product and investing simultaneously? What does Jeff think of VCs giving product advice to founders? What should the founders look for? What advice does Jeff give to the common question of "how do I get into investing and VC"?

3.) Why does Jeff disagree with the platform shift and the downturn in consumer mobile? What core innovations will drive the next wave of consumer mobile? Valuations in the space are often lofty, how does Jeff think about price and evaluate his own price sensitivity? How does Jeff think about scalable customer acquisition today in a world where incumbents dominate and price up the traditional channels?

4.) Jeff has said before that "investors treat crypto teams as if they are superhuman", what makes Jeff think this? How do their interactions differ than towards non-crypto teams? Why are lofty expectations dangerous for valuations? How does that put undue pressure on employees? Why are lofty expectations dangerous for product development? How do they affect the product roadmap negatively?

5.) How does Jeff approach the diligence aspect when it comes to investing? What have been some of his major lessons from making over 35 investments on the right diligence framework? How do shortened fundraising cycles negatively affect investor diligence processes? What can founders and investors do under these constrained time frames?

6.) Having worked with some of the greats from Doug Leone to Bill Gurley, what are some of the common traits in how the very best investors engage with founders? What were Jeff's personal learnings from seeing these greats in action? How did it change the way Jeff thinks about founder interaction and engagement?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: The Catcher In The RyeGoogled

Jeff’s Most Recent Investment: Radar Relay

As always you can follow HarryThe Twenty Minute VC and Jeff on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Nov 12, 2018

Leo Polovets is a General Partner @ Susa Ventures, one of the valley's leading early-stage seed funds with a portfolio including the likes of Flexport, Robinhood, Lendup, Qadium, Rigetti, the list goes on. As for Leo, prior to joining the world of VC, he started his career as the second non-founding engineer at LinkedIn. After two years at LinkedIn, Leo spent 3 years at Google, largely working on real-time payment fraud detection. Finally, his last stop pre-Susa involved spending 4 years at Factual, a location data platform.

In Today’s Episode You Will Learn:

1.) How Leo made his way into the world of VC from being the 2nd non-founding engineer at LinkedIn?

2.) Why does Leo believe that the hailed "warm intro" is actually dumb? What are the biggest drawbacks to this being commonplace in our ecosystem? What does Leo believe the mindset of investors should be instead? How does Leo filter through cold inbound? What are the 4 elements Leo looks for in all inbound? What can founders do to really make them stand out?

3.) Leo has previously heavily emphasised the importance of moats, how does Leo define moats and defensibility? When do founders have to think about moat building? Pre-product? Pre-launch? Pre-scaling? What questions suggest that a founders mindset is heavily oriented to moat building? With the majority of incumbents being usurped by platform shifts, does that not render moats significantly futile in the long term?

4.) What does Leo believe is the right way for investors to pass on an opportunity and communicate that to founders? What is wrong with the current way many do it? How does Leo present his opinion without getting into an argument with the founder on reasoning? What feedback has Leo been given from founders that has changed the way he thinks about being an investor?

5.) Controversial capitals Round:

  • Ownerships is built on first check? Agree or disagree and why?
  • Whether it is a $6m, $8m or $12m, if it is at seed, it is so early that price really does not matter so much? Agree or disagree and why?
  • There is no point VCs spending their time with struggling companies in the portfolio. At best they return cents on the dollar. Only work with the outperformers to drive returns. Agree or disagree and why?

Items Mentioned In Today’s Show:

Leo’s Fave Book: Elad Gil's High Growth Handbook

Leo’s Most Recent Investment: Interviewing.io

As always you can follow HarryThe Twenty Minute VC and Leo on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

Nov 9, 2018

Ooshma Garg is the Founder & CEO @ Gobble, the startup that allows you to cook a fresh homemade dinner in just 15 minutes. To date, Ooshma has raised over $30m in funding for Gobble from some of the best in the business including Initialized Capital, Keith Rabois, Reid Hoffman, Founder Collective, Felicis, Andreesen Horowitz and Thrive just to name a few. As for Ooshma, prior to founding Gobble she founded Anapata, an online site that matches students looking for jobs with potential employers. The company was ultimately acquired by LawWerx.

In Today’s Episode You Will Learn:

1.) How Ooshma made her way from Wall St to changing the way America eats with Gobble today?

2.) Everyone has an opinion on the food delivery space with the public nature of Blue Apron, what does Ooshma mean when she says "small and mighty beats loud and weak"? Why did Ooshma not take the path of other competitors in the space of racing big and running fast? What is Ooshma's advice to founders on dilution and raise amounts?

3.) Would Ooshma agree with Alex @ LSVP that marketing portfolios are like venture portfolios, diversified and then double down? Would Ooshma agree with the concern around unfeasible CACs due to incumbents bidding them up on major platforms? Where does Ooshma see blue ocean when it comes to marketing channel success?

4.) What does Ooshma mean when she says "success is survival"? Why is capital efficiency even more important in online/offline businesses? What are some of Ooshma's examples of her "wartime approach" to capital efficiency? How does Ooshma explain this more sustainable growth to the growth-hungry VC community? Who is to blame for the insatiable desire for unreasonable growth; the founders or the VCs?

5.) Ooshma has raised over $30m with Gobble, analysing herself in fundraising, what does Ooshma believe she did particularly well during the raise and advise other founders to do? What elements would she like to improve upon for the next round? What is the story behind how Ooshma sprinted down the 101 to get Keith Rabois as an angel?

Items Mentioned In Today’s Show:

Ooshma’s Fave Book: The Wind-Up Bird Chronicle 

As always you can follow HarryThe Twenty Minute VC and Ooshma on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Nov 5, 2018

Avidan Ross is the Founding Partner @ Root Ventures, one of Silicon Valley's most exciting newer generation of funds dedicated to backing bold engineers at seed. To date they have backed some incredible companies such as Nautilus Labs, Dusty Robotics, Tortuga AgTech and Instrumental.ai just to name a few. Prior to founding Root, Avidan was CTO at The CIM Group, with an aggregate of $15Bn AUM, Avidan was responsible for establishing the company’s technical vision and leading all aspects of the company's technology investment. Before that, he built algorithmic trading platforms as Director of Technology at WHW Capital. 

In Today’s Episode You Will Learn:

1.) How Avidan went from building algorithmic trading platforms to back the next generation of revolutionary engineers with Root?

2.) What does Avidan mean when he says "the peace dividends of the autonomous car wars will generate more value outside of transportation?" How does the commoditisation of these core components affect subsequent industries? With their commoditisation, does it not become a raise to the bottom on price and margin?

3.) How does Avidan approach the layering on new software products to emerging hardware devices? What does this mean for the margin required both for the hardware and the software? How does Avidan's investor mentality alter when investing in hardware vs software?

4.) Why does Avidan believe "old and boring industries are the most exciting to build software in?" How does Avidan approach the common problem of customer education and selling to a customer base that does not want to talk to you and does not believe in your product? What do founders selling in these industries need to focus on to break through?

5.) How does Avidan assess the current landscape in terms of the quality and quantity of engineer CEOs? Why does Avidan believe the MBA CEO will be replaced by engineers? How has Avidan seen a variance in the background in the entrepreneurs innovating in "old and boring" industries?

Items Mentioned In Today’s Show:

Avidan’s Fave Book: Drive by Daniel Pink

Avidan’s Most Recent Investment: Dusty Robotics

As always you can follow HarryThe Twenty Minute VC and Avidan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Nov 2, 2018

Ryan Caldbeck is the Founder & CEO @ CircleUp, the startup creating a transparent and efficient market to drive innovation for consumer brands. To date, Ryan has raised over $50m with CircleUp from some friends and prior guests of the show including USV, Collaborative Fund and Canaan Partners just to name a few. Prior to CircleUp, Ryan spent nearly 7 years investing in consumer products with the likes of TSG Consumer Partners and Encore Consumer Capital. As a result of Ryan's success with CircleUp he has been recognised as a "Titan of Retail" by Bloomberg and "40 Under 40" by the San Francisco Business Times.

In Today’s Episode You Will Learn:

1.) How Ryan made his way into the world of consumer investing and what the realisation moment was for him that the market needed a solution, CircleUp?

2.) Why does Ryan believe that venture capital has a fundamental problem? What is it about the economics of funds that Ryan has a problem with? Who is to blame for this situation; the LPs who fund it or the AUM hungry VCs? Why does Ryan believe the majority of micro VCs are micro as that is all they could raise? Is that really fair or true?

3.) Why does Ryan fundamentally believe the LP ecosystem and mechanism for backing funds is inherently broken? What is so wrong with current LP incentives? What does Ryan believe can be done to encourage more risk-taking and innovation from within the LP class?

4.) Recognising the antiquated nature of much of VC, what does Ryan believe the future of VC looks like? How will we see the use of data impact both sourcing and investment decision-making? Where does Ryan believe it has the most potential? Where is data so sparse that it will be challenging? How does Ryan believe the best managers of the future will use data?

5.) Consumer brands and DNVBs are riding high today, does Ryan believe we are in a consumer bubble? What does Ryan believe is so wrong about how the majority of the current crop of VCs analyse consumer businesses? How should they be analysed? Why does Ryan believe consumer exits will be smaller? Is it fair to say consumer is more capital intensive and largely sells for 1.6-1.8 EBITDA?

Items Mentioned In Today’s Show:

Ryan’s Fave Book: The Hard Thing About Hard Things

As always you can follow HarryThe Twenty Minute VC and Ryan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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