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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: 2019
Apr 22, 2019

Jeremy Liew is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Max Levchin’s Affirm, AppDynamics and many more incredible companies. As for Jeremy, he is best known for being the 1st investor in Snapchat and has also led investments in StitchFix, Affirm, Ripple, Giphy and Bonobos just to name a few. Previously, Jeremy was with AOL, first as SVP of corporate development and chief of staff to the CEO, and then as general manager of Netscape. Due to his incredible investing success, Jeremy has been featured on the Forbes Midas List multiple times.

In Today’s Episode You Will Learn:

1.) How Jeremy made his way into the world of venture with Lightspeed and came to be one of the valley's leading consumer investors and minds?

2.) How does Jeremy think about and approach sourcing today? How has mindset on sourcing shifted over the last decade? For a new VC, what would Jeremy advise them in terms of building them benchmark for distinguishing between good and great? How does Jeremy distinguish between good and great? Who does Jeremy believe is the most naturally gifted sourcer and hunter he has worked with?

3.) What does Jeremy mean when he says, "it is more important to be right than contrarian"? From winning some of the hottest deals, what have been Jeremy's lessons on what it takes to win the most competitive? What does he mean when he says, "you have to find your home advantage"? Should investors spend time amplifying their strengths or improving their weaknesses? How does Jeremy think about the round compression timelines on hot deals today? How can investors and founders build relationships fast?

4.) Why does Jeremy believe that founder to VC engagement can be similar to a driving instructor and student? What are the biggest mistakes startups make when they hit initial traction and start to scale? WHat patterns has Jeremy seen? How can founders avoid them?

5.) How does Jeremy fundamentally structure his week and time? What time is devoted to internal meetings and partnership meetings? How much time is allocated to the existing portfolio? How much time is spent with new prospective companies? What is Jeremy's favourite and least favourite activities within the role?

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

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

Apr 19, 2019

Dylan Field is the Founder & CEO @ Figma, the startup that provides a better way to design, prototype and collaborate, all in the browser. To date, Dylan has raised over $82m in funding from some of the world's best investors including Sequoia, Greylock, Kleiner Perkins, Founders Fund, Index Ventures and more. Prior to changing the world of design with Figma, Dylan held roles at Flipboard, Microsoft and LinkedIn and was part of the renowned Thiel Fellowship.

In Today’s Episode You Will Learn:

1.) How Dylan made his way from Thiel fellow to changing the world of design and prototyping with Figma?

2.) What is the story behind the 4-year journey to the launch of their first product? How did Dylan maintain morale with such an extended window between creation and launch? What are the core challenges of building tools companies and getting initial traction? How did Dylan satiate VCs desire for fast growth with such a long period to launch? Is it possible to "go slow to go fast" with VC dollars?

3.) Sequoia led Figma's Series C, how did the round come together? What was it that made Dylan choose the lead investors for each of his rounds? How did this round compare to prior rounds led by Index, Kleiner and Greylock? How does Dylan advise founders to build relationships of trust and transparency with their VC in short period of time?

4.) How did Dylan approach the topic of board construction? What did he most want to get out of his board? What have been some of Dylan's biggest learnings when it comes to board management? What has Dylan found the most challenging element?

5.) As a young founder himself, where does Dylan see commonalities in the mistakes that other young founders make today? As a young founder, how has Dylan been able to hire A** talent execs? What have been some of the biggest learnings on team assembly and construction through the process?

Items Mentioned In Today’s Show:

Dylan’s Fave Book: Stronger, Faster, and More Beautiful

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

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

Apr 15, 2019

Dave Sobota is the Vice President of Corporate Development @ Instacart, the company that delivers your groceries in as little as 1 hour. To date the company has raised over $1.9Bn in funding from some of the very best investors and operators including Mike Moritz @ Sequoia, Jeff Jordan @ a16z, Aaron Levie @ Box, Sam Altman, Garry Tan and more incredible names. As for Dave, prior to Instacart, he was Director of Corporate Development @ Google for over 10 years and before that was with leading law firm, Wilson Sonsini.

In Today’s Episode You Will Learn:

1.) How Dave made his way from the world of law to Director of Corporate Development at Google to his position at Instacart today?

2.) In 2016, we had 513 BC backed exits, 499 were M&A, so how does Dave assess the M&A landscape today? Why id Dave bullish on the future M&A environment, at least for the next 12 months? Where are his concerns around M&A clustering? How does Dave view the entrance of large scale PE into the tech M&A arena?

3.) From leading Google's M&A practice, what have been Dave's core learnings on whether an entrepreneur should sell their company or remain independent? Paul Graham once said, "startups only talk to corp dev when they are doing really well or really badly". Does Dave agree? What are the reasons a startup would not speak to corp dev? What is the right way for them to communicate this while leaving the door open for future conversations?

4.) How does Dave operationalise the tracking of the startup market and determine what startups he wants to meet? How does Dave like to and think about working with the VC community here? What does that relationship building process look like? In those early meetings, what are the core questions that founders must ask? How much of a role does price play for Dave when considering an acquisition?

5.) How can founders ensure when they sell their company, that it will be properly integrated? What answers from the acquirer suggest it will or will not be? From countless M&A processes, what do the best integrations look like post-acquisition? Where are mistakes often made? Does Dave agree with Paul Graham in stating it is a "gruelling" process?

Items Mentioned In Today’s Show:

Dave’s Fave Book: Lonesome Dove

Dave’s Most Recent Acquisition: Tenor

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.

Apr 12, 2019

Henry Ward is the Founder & CEO @ Carta, the startup that helps private companies, public companies, and investors manage their cap tables, valuations, investments, and equity plans. To date, Henry has raised over $147m in funding from some of the industries leading investors in USV, Spark, K9 Ventures and Meritech and then also leading founders including Flexport's Ryan Petersen, Transferwise's Taavet Hinrikus and Slack's Stewart Butterfield. Prior to founding Carta, Henry was Founder of SecondSight, a portfolio optimization platform for retail investors.

In Today’s Episode You Will Learn:

1.) How Henry made his way into the world of startups and came to found the gamechanger of cap tables and valuations with Carta?

2.) What does Henry mean by the term "executive half-life"? How does Henry determine between an exec that can scale with the company and an exec that cannot? What are the leading indicators? When weaknesses are revealed, how does this manifest itself? Does the exec open up and admit to it or does the leadership team have to be proactive?

3.) Question from Manu @ K9: As a first time CEO, what have been the biggest personal challenges for Henry in the scaling of himself? Why does Henry think it is unfair founders are given exemption from blame in scaling but execs are not? How does Henry make decisions differently now to the early days? What have been the improvements?

4.) How does Henry buck the conventional wisdom with his willingness to go after very small markets? What does the N of 1 vs 1of N rule mean here? Why does Henry believe the N of 1 markets is the most attractive? What are the core advantages to owning your market? How can founders think about insertion points? When is the right time to add additional products? How does Henry respond to the traditional notion of "focus"?

5.) Why does Henry believe most founders are afraid to put investors to work? If fundraising is, as Henry suggests "an auction process", what can founders do to optimise it? How does Henry approach the element of value creation and value extraction? How does this influence his approach to pricing? How does Henry think more tech founders can leverage acquiring services businesses and automating their processes over time? Where is the arbitrage in pricing here?

Items Mentioned In Today’s Show:

Henry’s Fave Book: The Essays of Warren Buffett: Lessons for Corporate America

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

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

Apr 8, 2019

Dayna Grayson is a Partner @ NEA, one of the leading venture firms over the last 4 decades with a portfolio including the likes of Opendoor, Jet.com, Uber, WorkDay, Plaid, Box and many more incredible companies. As for Dayna, she has led the firm's investments in the likes of Desktop Metal, Formlabs, Onshape, Glamsquad, Framebridge and Curalate, just to name a few. Prior to joining NEA, Dayna was an investor at North Bridge Venture Partners where she championed companies including Camiant (acquired by Tekelec) and Tapjoy. Before venture Dayna was an engineer at Eye Response Technologies, later acquired by Dynavox Mayer-Johnson and also a product designer at Blackbaud (BLKB), the leading global provider of software to nonprofit organizations.

In Today’s Episode You Will Learn:

1.) How Dayna made her way into the world of venture and came to be a Partner at NEA from her roots in product design and engineering?

2.) Sourcing: How does Dayna approach the sourcing component of venture today? What does the deck filtering process look like to Dayna, prior to meeting? What has Dayna found works best in really building rapport in the first meetings? What does the conviction building process look like for Dayna from there? If negative, how has Dayna found is the most effective way to say no?

3.) Decision-Making: How does Dayna think about optimising the investment decision-making process? How does Dayna balance between data vs gut? Does NEA require unanimous decision-making? Why does Dayna believe that at A or earlier, the price really does not matter? When does price really become a big issue?

4.) Evolution of Expectations: How does Dayna believe entrepreneurial expectations of VC has changed over the last decade. Where does Dayna believe investors can really provide the most value? Which board member has been the most impressive to Dayna when sitting alongside them on the board? Why?

Items Mentioned In Today’s Show:

Dayna’s Fave Book: Dopesick: Dealers, Doctors and the Drug Company that Addicted America

Dayna's Most Recent Investment: WhireWheel

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

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

Apr 5, 2019

Jeff Russakow is the CEO @ Boosted, the startup producing vehicle grade electric skateboards rethinking how we travel. To date, they have raised $74m in funding from the likes of Khosla Ventures, iNovia Capital, Andreessen Horowitz and our friends at Initialized. Prior to Boosted, Jeff was CEO @ Gimbal where he doubled revenue in his first year and added 80 new enterprise clients. Before that, Jeff was the CEO @ Findly where he grew the company to 450 employees and 20m end users. Jeff also enjoyed prior roles with the likes of Symantec, Adobe, SAP and Yahoo.

In Today’s Episode You Will Learn:

1.) How Jeff made his way from leading enterprise CEO to re-thinking the way we travel today as CEO of Boosted?

2.) How does Jeff analyse the current sentiment to fundraising in the valley, specifically with regards to business construction? How has Jeff seen the investor class fundamentally transition over the last 20 years? When approaching investor selection, what is the 1 question that Jeff always asks? Where do founders often make mistakes here?

3.) Having raised the $60m round in 2018, how does Jeff approach the theme of capital efficiency today with Boosted? How does Jeff determine when is the right time to pour fuel on the fire? Why is Series B often the most challenging phase when considering the focus on unit economics and vision simultaneously?

4.) What is Jeff's gut reaction to the statement, "hardware is hard"? Why does Jeff feel this to be a glib statement that misses the point? How does Jeff respond to the criticism of the commodity element of hard, easy to replicate and copy? How would Jeff like to see the investor class change their mindset to hardware? What is the right way to approach it?

5.) What are the core elements required for a successful CEO transition? For a potentially incoming CEO, what must they be wary of with regards to the information conveyed to them by investors of the company? Where has Jeff seen many go wrong in CEO transitions? What can the founders do to make this process as smooth as possible?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: The Missing Piece 

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.

 

Apr 1, 2019

Garry Tan is the Co-Founder and Managing Partner @ Initialized Capital, one of the West Coast's leading early-stage funds with a portfolio including the likes of Coinbase, Instacart, Cruise, Flexport and Opendoor, just to name a few. As for Garry, before co-founding Initialized, he was a partner at Y Combinator for nearly five years where he advised and funded over 600 companies. He was also co-founder of YC-backed blog platform Posterous (acquired by Twitter in 2012). Before that he was employee #10 at Palantir, where he was a founding member of the engineering team for Palantir's financial analysis product, and also fun fact, Garry designed Palantir's logo.

In Today’s Episode You Will Learn:

1.) How Garry made his way from Founder and YC Partner to managing over $500m AUM today with his leading of Initialized? How did Garry's investment mindset change with the transition from angel to an institutional investor?

2.) What does Garry believe is the one thing pre-seed and seed investors must do that is more important than anything else? What relationship to the very best founders have with failure? How do they think about and approach it? How has Garry seen his own conviction building process in founders change over time? How does Garry approach the turning down of opportunities? What is the right way to deliver that feedback?

3.) Ownership: Initialized's funds have scaled from Fund I being $7m to Fund 4 being $225m, how have their ownership requirements changed with the evolution of their fund size? How does Garry think about collaboration and co-opetition with others funds as a result? What are the core challenges here?

4.) Price Sensitivity: With the larger fund and slightly more flexibility, how does Garry evaluate his own price sensitivity? What deal has Garry passed on due to price and it has stuck with him and taught him a valuable lesson? On pricing, how does Garry and Initialized approach reserve allocation?

5.) Investment Decision-Making: Garry has previously said "decision-making is a differentiator", what do Initialized do to ensure the highest quality of internal discussion and decision-making? How do they approach unanimous vs single partner decision-making? How does Initialized approach internal attribution with this in mind?

Items Mentioned In Today’s Show:

Garry’s Fave Book: Peter Thiel's Zero To OnePaul Graham's Hackers and Painters

Garry’s Most Recent Investment: Standard Cognition

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

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

Mar 29, 2019

Joel Gascoigne is the Co-Founder & CEO @ Buffer, the social media management tool that makes it easy for businesses and marketing teams to schedule posts, analyze performance, and manage all their accounts in one place. They had raised both seed and Series A rounds but last summer, spent $3.3m to buy out the majority of their Series A investors, making them much more independent. Joel now runs Buffer as a profitable business with $2m in profit in 2017 and $3m in 2018. Before co-founding Buffer, Joel co-founded OnePage and StartupMill and was a web developer in the UK.

In Today’s Episode You Will Learn:

1.) How Joel made his way from web developer in the UK to founder of Buffer, in 2018 a business that did $3m in profit?

2.) What does Joel mean when he says that "fundraising is a bigger decision than most people realise"? At what moments does Joel believe that the founders are no longer the boss? When did Joel feel he was no longer the boss? What does Joel wish founders knew more about the VC process and mechanics? What questions must they ask VCs?

3.) Would Joel agree with Anand Sanwal, previously on the show that "VCs foie-gras their startups", forcing synthetic growth? What is the right way for founders to respond to this pressure? How did Joel personally handle the pressure? How does Joel assess and analyse the current VC ecosystem? What would he most like to change?

4.) There was a time when individuals did not want Joel to be CEO, how did Joel deal with that? What would Joel advise founders in the same position? What are the right steps to take? Joel then lost his co-founder, how was that process for Joel? What does he know now that he wishes he had known at the beginning of that process? How does he look to retain that level of support and guidance from someone other than a co-founder?

5.) What does Joel mean when he says, "leaders must lean into transparency"? Are there any limitations to being overly transparent? Now as a profitable company, how does Joel think about profit sharing with the team? What does profitable status allow the team to achieve and do that is not normally possible for VC backed co's?

Items Mentioned In Today’s Show:

Joel’s Fave Book: A Little Life

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.

Mar 25, 2019

Alex Clayton is a Partner @ Spark Capital, one of the leading firms of the last decade with a portfolio including the likes of Slack, Postmates, Oculus, Cruise, Twitter, the list goes on. As for Alex, he co-led Spark's investments in Pendo and Outreach and then led Spark's investments in Justworks, Braze (Appboy) and JFrog. Before Spark, Alex spent three years at Redpoint Ventures as a senior associate where he sourced or was actively involved in the firm's investments in Duo Security, JustWorks, RelateIQ (Salesforce.com), Infer, Lifesize and Sourcegraph. Prior to joining Redpoint, Alex was in the TMT investment-banking division of Goldman Sachs where he worked with Intuit, Yelp, SanDisk, and others. Fun fact, in the past Alex played on the ATP World Tennis Tour, competing in the U.S. Open and many other ATP events.

In Today’s Episode You Will Learn:

1.) How Alex made his way from the world of investment banking with Goldman Sachs to one of the valley rising stars in the world of enterprise investing? What were Alex's biggest takeaways from his time at Redpoint and working with Tom Tunguz?

2.) How does Alex think about and approach sourcing today? How does Alex find most of his deals? How does Alex breakdown both thesis and network driven sourcing? How does sourcing at growth differ to sourcing at the early stage? If Alex has to meet founders when they are not raising, what does Alex advise founders who are told that you should not "always be raising"?

3.) How does Alex think about market sizing and evaluation today? What does he mean when he says he closely examines "market depth"? How does Alex determine whether a company has the ability to scale from a niche into a much larger TAM? What are the risks Alex is willing vs not willing to take when it comes to market?

4.) How does Alex think about competitor analysis when evaluating an opportunity today? In a world of almost infinite capital, does Alex believe that cash alone is a significant moat for competition? In customer calls when they discuss competition, what excites Alex to hear? How does Alex structure those customer reference calls?

5.) Alex has studied some of the best in class when it comes to SaaS, what do the best in class look like when it comes to: 1.) Quota attainment. 2.) Payback period. 3.) Net dollar retention and churn? 4.) Capital efficiency? Growth rate? Ultimately, what does Alex believe that it takes to go public having studied so many S1s?

Items Mentioned In Today’s Show:

Alex’s Fave Book: Zero to One by Peter Thiel

Alex’s Most Recent Investment: Braze

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

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

Mar 18, 2019

Mike Hirshland is the Co-founder of Resolute Ventures, one of the leading pre-seed and seed stage funds of the last decade having recently announced their new $75m Fund IV. In prior funds they have the likes of OpenDoor, Mixmax, Greenhouse, AppZen and more incredible companies. As for Mike, prior to founding Resolute, he founded Dogpatch Labs, the community which helped launch over 350 companies including Instagram. Before Dogpatch, Mike was a partner with Polaris Venture Partners from 1999-2011, where he was the original seed investor behind Automattic, Q1 Labs (acquired by IBM for $600 million), Quantcast and KISSmetrics.

In Today’s Episode You Will Learn:

1.) How Mike made his way from a legal clerk in the US Supreme Court to founding his own venture firm in the form of Resolute Ventures?

2.) What does Mike mean when he says Resolute invest at the "old seed stage?" What stage of development and traction are the companies at this stage? Why does seed investing out of a $Bn fund not make sense to Mike? What are the acceptable vs unacceptable risks at this stage?

3.) How does Mike think and assess portfolio construction today? How many lines in the portfolio is enough to be sufficiently diversified? How does Mike think about ownership given his thesis on diversification? How does Mike assess his own price sensitivity today? How does Mike think about loss ratio within the portfolio today?

4.) What are the ideal attributes of the founder/VC relationship to Mike? Is it right for the investor to also be friends with their founders? What can founders do to really build and deepen relationships with investors both during and outside of official fundraises? Where does Mike often see founders making mistakes here?

5.) How does Mike think about the right time to establish a board? What does Mike advise founders in terms of board composition in the early days? How does Mike look to build a sense of "board intimacy" with his founders? Why does Mike believe that there is a "counter-productivity to boards at seed"?

Items Mentioned In Today’s Show:

Mike’s Fave Book: A Little Life

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

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

Mar 15, 2019

Adam Pritzker is the Chairman & CEO @ Assembled Brands, a holding company providing working capital and financial services to emerging brands. In October 2018, they raised $100m in development capital from the prestigious Oaktree Capital Management. As for Adam, he is also a co-founder of General Assembly where during his tenure, prior to its acquisition by Addecco Group, he served as Chief Creative Officer, Chief Product Officer, and Chairman. For his entrepreneurial endeavors, Adam was featured in Forbes’ 30 Under 30, Vanity Fair’s The Next Establishment, Inc. Magazine’s 30 Under 30, and Business Insider’s Silicon Alley 100.

In Today’s Episode You Will Learn:

1.) How Adam made his way into the world of startups with the co-founding of General Assembly and how that led to his founding Assembled Brands and financing the future of brands?

2.) Why is Adam optimistic about the current state of the consumer brand and retail environment? How does Adam respond to Alex Taussig @ Lightspeed's suggestion of the "re-platforming of retail"? How does Adam approach the changing demographic of consumer spend? What does this mean for both the brands and the channels they use to acquire customers? Does Adam believe we are in a consumer bubble today?

3.) How does Adam think about the lack of free and open distribution today for consumer companies? Are the traditional channels now too expensive to acquire customers on? How does Adam advise consumer founders on the saturation rate of marketing channels? How can they foresee the ceiling ahead of time?

4.) Adam has previously stated that Instagram is the new QVC, what did he mean by that? What type of consumer brand is Instagram best suited for? Why does Adam believe that in many cases the venture financing method is suboptimal and wrong for these scaling brands? What can founders who have taken VC funds and now seen it was potentially a mistake do?

5.) Why does Adam believe that the "infrastructure to power emerging brands is broken"? How can the current stack and infrastructure for brands be improved? What metrics should consumer founders really hone in on today? What sort of metrics suggests a brand is VC backable vs is not VC backable? How does Adam think about the ability of the consumer brand space to provide venture returns at scale?

Items Mentioned In Today’s Show:

Adam’s Fave Book: (1.) The Coddling of the American Mind: How Good Intentions and Bad Ideas Are Setting Up a Generation for Failure(2.) The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It

Adam's Most Recent Investment: Felix Gray 

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

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

Mar 11, 2019

Victoria Treyger is a General Partner & Managing Director @ Felicis Ventures, one of the leading venture firms of the last decade backing 2 unicorns per year since founding including Shopify, OpenDoor, Flexport, Adyen, Twitch, Fitbit and many more. At Felicis, Victoria led the firm’s investments in prior 20VC guest Assaf Wand @ Hippo, Sentio, Sentilink, Blume, Floravere, and other stealth brands. Prior to joining Felicis, Victoria was Chief Revenue Officer of Kabbage. During her six-year tenure, Victoria and her team were instrumental in scaling revenue into the hundreds of millions of dollars and delivered a compound annual growth rate of over 100%. Victoria’s deep operating experience also includes leadership roles at Amazon, American Express, Travelocity, and RingCentral.

In Today’s Episode You Will Learn:

1.) How Victoria made her way into the world of VC as GP @ Felicis today having scaled revenue into the 100s of millions with Kabbage on the operating side of the table?

2.) Having just made the move from the world of operations, what are the most surprising aspects of venture? What elements have you found to be the most challenging? How does Victoria think about what it takes to be the most effective coach? What can the investor do to build that level of trust and transparency with the founder?

3.) In terms of being a board member, how involved does Victoria think the board member should be? Who is the best board member Victoria has worked with? What made them so special? What are Victoria's biggest pieces of advice to founders when it comes to how to run an efficiency board? What is the right way for founders to think about board composition?

4.) What 3 trends in the world of consumer and CPG make Victoria so excited to be investing in the space today? What has fundamentally changed about the distribution of those products that changes the way we consume the products? Does this mean Victoria would disagree we are in a D2C bubble today?

5.) Speaking of distribution, how does Victoria respond to the suggestion "there is a lack of free and open distribution today" with customer acquisition costs being so expensive? How does Victoria think about the consumer and CPG space's ability to provide venture returns at scale moving forward?

Items Mentioned In Today’s Show:

Victoria’s Fave Book: Mindset: How You Can Fulfil Your PotentialPersonal History

Victoria’s Most Recent Investment: SentiLink

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

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

Mar 8, 2019

Austen Allred is the Founder & CEO @ Lambda School, a 9 month, immersive program that gives you the tools and training you need to launch your new career—from the comfort of your own home. As a Lambda student, you pay nothing until you’re earning $50k or more. And if you don’t, it’s free. To date, Austen has raised over $48m with Lambda from a personal favourite of mine Bedrock, GGV, GV, Stripe and Ashton Kutcher just to name a few. Prior to founding Lambda, Austen was Senior Manager for Growth @ LendUp and before that co-founded Grasswire.

In Today’s Episode You Will Learn:

1.) How Austen made his way from being broke, sleeping in a car to founding one of Silicon Valley's hottest startups in the form of Lambda School?

2.) Austen lived in his car for many months in Palo Alto, what did Austen come to learn about himself from that experience? Before Austen has said, "it is not about money", so how would Austen describe his personal relationship to money? Consequently, what does this mean for Austen's relationship to risk?

3.) Austen previously stated he was "determined to never raise VC again before Lambda School". 2 years and $47m later, what changed in his attitude to raising VC? How mus every founder examine their business model before raising VC? What is the one question they must ask pre-raise?

4.) Austen recently raised a $30m Series B round, how did that round come about? What is Austen's biggest advice when it comes to investor selection? How does Austen think about when is the right time to raise big? How does that impact and affect operating mentality? What was it about Geoff Lewis that made Austen take his offer over others?

5.) Question from Geoff @ Bedrock: How does Austen iterate on all aspects of the business so fast? Why does Austen believe that the speed and quality of decisions are not mutually exclusive? Why does Austen believe the faster you ship, the higher quality they will be? How does Austen determine which experiments to stick with vs drop?

Items Mentioned In Today’s Show:

Austen’s Fave Book: Les MiserablesThe Wright Brothers

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

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

Mar 4, 2019

Jeff Richards is Managing Partner @ GGV Capital, one of the leading venture firms of the last decade with a portfolio including the likes of Alibaba, Slack, Square, Xiaomi, Peloton, OpenDoor, just to name a few. As for Jeff, he sits on the board of or is an observer at BigCommerce, Brightwheel, Gladly, Lambda School, Namely and Tile just to name a few. Jeff also led GGV’s investments in Buddy Media (acquired by Salesforce), HotelTonight, Flipboard and has been actively involved in GGV’s investments in Opendoor, Domo, Square and Wish. Prior to joining GGV, Jeff founded two software companies: R4 (acquired by VeriSign), and QuantumShift, backed by Texas Pacific Group (TPG).

In Today’s Episode You Will Learn:

1.) How Jeff made his way into the world of VC with GGV from founding and scaling 2 software companies in the 90s? What were Jeff's 2 biggest takeaways from having the company he founded raise over $100m then go to $0 in the crash?

2.) How does Jeff approach and see the transition from founder to CEO today? When does this transition need to occur? How do first-time founders differ compared to experienced serial entrepreneurs when it comes to building their teams? Where do they often struggle or make mistakes? What advice does Jeff offer them?

3.) Jeff has previously said, "do not raise for the highest valuation", what is his thinking here? What specific examples does Jeff have of why it can hurt and damage both the founder and the company? How does Jeff think about his own price sensitivity today? How does he determine when a stretch is a stretch too far? From backing the likes of Alibaba, Xiaomi and Didi, what were his biggest takeaways when it came to price?

4.) Decision-making is one of the only products venture has, how does Jeff and GGV approach decision-making as a firm today? Being a slightly later stage firm, how do they think about reserve allocation? What does the re-investment decision-making process look like? How does GGV think about attribution as a firm today? What are the benefits?

5.) What advice would Jeff give to an individual that has just entered VC? What does Jeff know now that he wishes he had known at the beginning? How does Jeff think about what it takes to be a truly special board member? What one or two things can a board member do to move the needle in their relationship with their founder?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: In an Uncertain World: Tough Choices from Wall Street to Washington

Jeff’s Most Recent Investment: Lambda SchoolElectric

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.

Mar 1, 2019

Rob Sadow is the Founder & CEO @ Scoop, the startup that dramatically improves your commute providing convenient carpools with co-workers and neighbours. To date, Rob has raised over $37m in funding for Scoop from the likes of Danny Rimer @ Index, Brook Porter @ G2VP, Zaw Thet @ Signia Venture Partners and BMW i Ventures just to name a few. Before founding Scoop, Rob was a Manager @ Bain & Company and before that spent time in Israel with Better Place, working to provide electric vehicle networks to help accelerate the global transition to sustainable transportation.

In Today’s Episode You Will Learn:

1.) How Rob made his way from the world of consulting and Bain to founding the future of convenient commutes with Scoop?

2.) How does Rob approach key decisions? What does Brook Porter @ G2VP mean when he says, "from a first principles perspective"? How does Rob determine when to make decisions with the head or the heart? Does Rob agree with Fred Destin, "as a founder, decisions are never perfect, it is about batting average"? Where does Rob see many make mistakes when it comes to decision-making?

3.) How does Rob find the dynamics of working with his brother as his co-founder? What are some of the core challenges? How does one make it scale and how does the relationship need to change over time? What is Rob's biggest advice to others when thinking about the person they partner with?

4.) How does Rob think about board construction? What have been some of Rob's biggest lessons in really using your board to get the most out of them? What works well for this? What does not work? How can founders create this level of relationship with their board members? Should founders direct their ask to specific individuals when soliciting help from their board?

5.) Why does Rob believe that they have next to no attrition of employees at Scoop? What have been some of Rob's biggest lessons when it comes to both culture creation and maintenance? How does Rob think leaders can invest more in their employees? What does this look like? Where do many go wrong or misallocate?

Items Mentioned In Today’s Show:

Rob’s Fave Book: The Wheel of Time

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

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

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.

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