20VC: Why Startup Valuations Are Not As Overpriced As You Think, How To Determine Whether An Investor Is Truly Aligned To Your Mission and What 2 Traits Make The Truly Special Board Members with Jason Brown, Founder & CEO @ Tally


Jason Brown is the Founder & CEO @ Tally, the startup that allows you to pay off your credit card debt faster and save money. To date, Jason has raised over $92m for Tally from the likes of Mamoon @ Kleiner, Angela @ a16z, Nikhil @ Shasta and Aileen @ Cowboy just to name a few. As for Jason, prior to Tally, he spent 5 years as the Founder and CEO Kleiner Perkins backed, Gen110. Before that Jason founded Bask, a company providing both technical support and pro-active maintenance.



In Today’s Episode You Will Learn:

1.) How Jason came to change the world of consumer finance with Tally having spent 5 years in the solar financing sector and even a year in venture? Given his prior entrepreneurial activities, does Jason agree with Joe Fernande @ JoyMode that “serial entrepreneurship is overrated”?

2.) Does Jason believe that founders should always be raising? What is the right way to truly determine whether an investor is aligned to your mission? What should you look for in how they behave and speak? How does Jason like to build relationships with investors pre-term sheet? Is Jason concerned by the compressed fundraising timelines today?

3.) Why does Jason believe that VC funded companies are largely not over-priced? What elements of the macro-economy does Jason attribute as the reason for the high valuations today? Why does Jason believe that we should not celebrate new fundraising? Is the celebration not good for the morale of the team? What should we celebrate instead?

4.) Why does Jason believe that the target for investors is they provide no value? What are you looking to avoid? What are the core ways an investor can damage the success of a company? What can founders do to truly extract the most from their investor base? Does Jason believe one should focus on the VC partner or the firm? Why?

5.) What does Jason believe makes the best board members? What advice would Jason give to new board members on how they can truly be the best board member? Why does Jason do onboarding sessions for all new board members? What does he look to instil in this process? What behaviour at the board should not be tolerated? How should the founder communicate this to their investor?

Items Mentioned In Today’s Show:

Jason’s Fave Book: Sapiens: A Brief History of Humankind

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

20VC: Why The Best Entrepreneurs Are Cockroaches, What Everyone Underestimates About Customer Acquisition & What You Don’t But Need To Know About Payback Periods with Josh Buckley, Founder & Chairman @ Mino Games

Josh Buckley Headshot

Josh Buckley manages a $50m early-stage fund and as an angel has built a portfolio that includes the likes of Clearbit (Chairman), Rippling, Boom Supersonic, Lattice, Embark and many more incredible companies. Josh is also the Founder & Chairman @ Mino Games, the gaming studio he scaled to $20m in annual revenue and raising $40m in funding for the company.



In Today’s Episode You Will Learn:

1.) How did Josh make his way into the world of startups at the age of just 15? How did that lead to becoming the youngest YC founder ever?

2.) What does Josh mean when he says, “the best entrepreneurs are cockroaches”? How does Josh think about capital efficiency today? Does Josh agree with Bill Gurley in stating the biggest challenge today is “the oversupply of capital”? How does Josh advise his portfolio today on raising big rounds? Capital efficiency? Burn rates?

3.) As both a fund manager and founder, what have been some of Josh’s biggest takeaways from now investing in 100+ companies as an angel? How has investing impacted Josh’s operating mentality? What are the benefits of angel investing? What are the potential dangers? What advice would Josh give to founders entering the world of angel investing?

4.) What are the biggest elements people underestimate when it comes to CAC? What have been Josh’s biggest lessons on the volatility of CAC over time? How are we seeing the platforms evolve and develop their tech and pricing? How important is channel diversity to Josh? What is balanced? What is not? What have been Josh’s biggest lessons when it comes to payback period and it changing over time?

Items Mentioned In Today’s Show:

Josh’s Fave Blog/ Newsletter: Paul Graham Blog

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

20VC: Ash Fontana on The 5 Core Characteristics That Make Data Valuable, What VCs Can Learn From Italian Craftsmen and Howard Marks & The Importance of Vertical Integration In Scaling Today


Ash Fontana is a Managing Director @ Zetta Venture Partners, the fund that invests in AI-first companies with B2B business models. As for Ash, prior to Zetta, he started the money side of AngelList, where, he launched online investing, created the first startup ‘index fund’. He also ran special projects like AngelList’s expansion into Europe and the UK. Simultaneously, Ash led syndicates and made investments in Canva, Mixmax and others. Before AngelList, Ash co-founded Topguest, a Founders Fund-backed company that built customer analytics technology and was ultimately sold in an 8 figure transaction 18 months after the company was founded.



In Today’s Episode You Will Learn:

1.) How Ash made his way into the world of venture with AngelList and how that led to his joining Zetta today, investing exclusively in AI? What did Ash’s time working on his family farm teach him about vertically integrated businesses? What were his biggest takeaways from AngelList and working alongside Naval?

2.) What does AI-first really mean to Ash? How crucial is it for companies to have proprietary datasets today? Are data moats truly defensible and real? What are the 5 characteristics that determine the level of defensibility of a dataset? How does Ash analyse the quality of a dataset? What does Ash do to determine if they are predictive of value?

3.) We often hear the term, “system of record”, why is Ash so much more excited by the “system of intelligence”? Why is the basis of competitive advantage shifting from SaaS today as a model? How do the margin structure vastly differ when comparing AI-first companies to SaaS companies? How does that mean one should view capital efficiency?

4.) What does Ash believe drives business model quality? What are the commonalities in the business models of those that have made it big? Why does Ash believe it is difficult for incumbent companies to become AI-first? How difficult is it for incumbents to acquire smaller AI-first firms and integrate their policies and technology?

5.) Why does Ash love Howard marks and what has been his biggest learnings from studying him? How has Ash applied these learnings to his investing today? What has Ash also learned from the Italian masters of design? How has this study helped Ash as a VC? What has Ash optimised lately? What is Ash’s favourite optimisation?

Items Mentioned In Today’s Show:

Ash’s Fave Book: The Strategy of Life: Teleology and Mechanics in Nineteenth-Century German Biology

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


20VC: Why Speed Is The Biggest Differentiator a Founder Can Have, How To Hire Seasoned Tier 1 Talent To An Early Stage Startup & How To Start, Scale and Manage Remote Teams with Domm Holland, Founder & CEO @ Fast


Dom Holland is the Founder & CEO @ Fast, the world’s fastest login and checkout with no more passwords, no more typing credit card details or shipping addresses. The special announcement today, Fast have just raised their seed round led by Jan Hammer @ Index, joined by Susa Ventures, Kleiner Perkins, Global Founders Capital and then angels including Nick Molnar, Founder @ Afterpay and proud to say I joined the round as an angel also. Prior to Fast, Domm was a Director @ Tap Tins, a network of smart tap-to-donate collection terminals. Domm was also the Founder & CEO @ Tow, an on-demand towing platform which transacted $50m in its first 4 years.



In Today’s Episode You Will Learn:

1.) How Domm made his way from founding an on-demand towing company in Queensland, Australia to founding one of Silicon Valley’s hottest new startups in Fast?

2.) What did Domm do in prior companies that worked and he will do again with Fast? What did not work and he will look to avoid? Does Domm agree with Joe Fernandez @ JoyMode in saying, “serial entrepreneurship is overrated”? What advice does Domm give to first-time founders? Where do they most often make mistakes?

3.) Over the last few years we have seen incredible innovation on the merchant side of payments with Stripe and Adyen but why does Domm believe we have seen no innovation on the consumer side? Why have large internet platforms not built it themselves? Does it have to be an independent 3rd party, external to Google, Facebook, Amazon etc?

4.) With the war for talent, rising rents and a lower standard of living, why did Domm choose SF as the base for Fast? How has the move been? What have been the biggest challenges? What would Domm advise founders contemplating moving to SF? How has Domm been able to hire some big hitter valley operators so early on? How does Domm think about equity sharing and optimising ESOP plans?

5.) Jan Hammer @ Index has discussed Domm’s work mentality, so how does Domm structure his day? What does Domm do to ensure he optimises every minute? What work habits has Dom found to be most effective? What has not worked? How does Domm think about balancing speed and quality when executing today?

Items Mentioned In Today’s Show:

Dom’s Fave Productivity Tool: Superhuman

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

20VC: Firstmark’s Rick Heitzmann on The Rise of Pre-Emptive Rounds, His Biggest Learnings From The Pinterest Board, 2 Things VCs Can Do To Prepare Their Companies For The Downturn and Why Now Is A Good Time to Be Contrarian and Invest In Consumer

Rick Heitzman Visuals

Rick Heitzmann is a Founder and Partner @ Firstmark Capital, one of the leading East Coast venture funds of the last decade with a portfolio including the likes of Airbnb, Pinterest, InVision, Shopify and Discord to name a few. As for Rick, he led the seed round for Pinterest and also led the deals from Firstmark in Ro, Riot Games, Draft Kings, Discord and Airbnb. Prior to founding FirstMark, Rick was an entrepreneur as a founding member at First Advantage which he helped grow and sell to First American (NYSE: FAF). Rick has been recognized by CB Insights and the New York Times as a Top 100 Venture Capitalist globally.



In Today’s Episode You Will Learn:

1.) How Rick made his way into the world of venture and came to found one of NYC’s leading venture funds in the form of Firstmark?

2.) How did seeing the booms and bust of the macro impact Rick’s investment mentality today? With the impending crash, what 2 things does Rick advise managers need to prepare their portfolio by doing? Does Rick agree with Bill Gurley in saying, “the biggest challenge of today is the over-supply of capital”?

3.) How has Rick seen his style of investing change over the last 20 years? How does Rick think about price sensitivity today? How has that changed over the years? How has Rick seen himself change and evolve as a board member? What does Rick believe makes the best board members? What advice would Rick give to someone who has gained their first board seat?

4.) How does Rick think about the structure of the Firstmark portfolio today? How important does Rick believe it is to have temporal diversification within the portfolio? How does Rick think about optimising investment decision-making processes at Firstmark? Why does Rick believe, despite the negatives, that attribution is fundamentally important?

5.) Does Rick believe that we are in a consumer bubble today? What are the core elements that pique Rick’s interest when analysing a consumer investment today? How does Rick think about CAC’s scaling way faster and higher than anyone expected? Why does Rick believe the duopoly of FB and Google is now over? Why does Rick believe that true venture size exits can still occur in consumer?

Items Mentioned In Today’s Show:

Rick’s Fave Book: Moneyball: The Art of Winning an Unfair Game

Rick’s Most Recent Investment: Crisp

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

20VC: Why Pre-Product Market Fit Is About Systems Design Not Engineering, The Right Way For Leaders To Approach Wartime Leadership Today & A Guide To Recruitment Forward Planning with Ryan Denehy, Founder & CEO @ Electric

Denehy Visual

Ryan Denehy is the Founder & CEO @ Electric.ai, the company that provides a world-class IT solution that’s centralized, secure, and lightning-fast. To date, Ryan has raised over $37m in funding from some dear friends of the show in Rich @ GGV, Bessemer, Primary, Bowery, just to name a few. As for Ryan, he started his career at the tender age of 17 launching an action sports video production company, which was acquired just 4 years later. Ryan then spent 5 years at USA Today in numerous different roles. Following USA Today, Ryan started his second company, Swarm, acquired by Groupon just 3 years later.



In Today’s Episode You Will Learn:

1.) How Ryan made his way into the world of startups from launching an action sports video production company at the age of 17?

2.) Having founded 2 prior companies, would Ryan agree with Joe Fernandez @ JoyMode in saying that “serial entrepreneurship is overrated”? What did he do right in the first 2 companies that he would look to do again? What did not work that he is avoiding? Where does Ryan most often see first-time founders make mistakes scaling?

3.) How does Ryan think about and assess wartime leadership? What is the right leadership style and approach to battle through the really tough times? Ryan’s investors talk of his speed of execution, how does Ryan balance the speed with the quality when it comes to execution? How has Ryan seen both his role and the way in which he executes it change with the scale of the company and of himself?

4.) How does Ryan thnk about and assess forward planning when it comes to recruitment? How should this recruitment planning align to fundraising? Why must it start before the fundraise? How does Ryan think about levelling up individuals internally vs hiring external candidates? How does Ryan think about and present internal expectation setting?

Items Mentioned In Today’s Show:

Ryan’s Fave Book: Barbarians At The Gate

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.

20VC: Inside The Mind of A Leading LP: How LPs Evaluate New Fund Managers on Everything from First Meeting to Portfolio Construction To Fees and Carry with Lisa Edgar, Managing Director @ Top Tier Capital Partners


Lisa Edgar is a Managing Director @ Top Tier Capital Partners, one of the leading venture fund of funds over the last decade. Included in their stellar fund portfolio is the likes of Index, Initialized, True Ventures, a16z and Boldstart, to name a few. Prior to Top Tier, Lisa was part of the asset management team at WR Hambrecht + Co focusing on new and emerging private equity funds. Before that, Lisa spent ten years at Horsley Bridge.



In Today’s Episode You Will Learn:

1.) How did Lisa make her way into the world of investing in funds and how did that lead to her becoming Managing Director at one of the leaders, Top Tier?

2.) Lisa has seen the boom and bust of the macroeconomy twice now, how has that impacted her mindset today when investing in funds? What have been the most prominent changes in the venture ecosystem that Lisa has seen over the last 20 years? What changes have been good? What changes have been bad?

3.) What is the best way to get in the room with LPs? Does it have to be through warm intro? What are the signs for the GP that that first meeting went well? If an LP does not respond to emails, does that mean they don’t want to do it? How does Lisa and Top Tier structure the investment decision-making process? How does that differ when re-investing in existing managers? Is it worth it for first-time funds to pitch institutions for fund 1 when they know they will not invest in the fund?

4.) How does Lisa think about GP commits today? How does Lisa look at what is reasonable and what is required? Is it individual and context-based? How does Lisa feel about different carry structures? Are kickers when past a certain return profile amenable to LPs?

5.) Lisa has seen some of the best emerging managers in the US over the last decade, what learnings does she have from them in terms of what separates the good from the great? How do they think about partnership dynamics? How do they think about firm culture? How do they think about generational transition?

Items Mentioned In Today’s Show:

Lisa’s Fave Book: From the Mixed-Up Files of Mrs. Basil E. Frankweiler

Lisa’s Most Recent Investment: Boldstart Ventures

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

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