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

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to for more information on the podcast, show notes, resources and more.
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Now displaying: March, 2023
Mar 31, 2023

Jackie Reses is the Chair and CEO of Lead Bank, a community bank in Kansas City.  Previously, she was the Executive Chairman of Square Financial Services and Capital Lead and Head of the People Team at Block Inc (Square). Prior, she had leadership positions at Yahoo! and was a Partner at Apax Partners Worldwide. Jackie also spent seven years at Goldman Sachs in mergers and acquisitions and the principal investment area. Jackie is on the board of directors of Endeavor, Affirm and Nubank. Previously, she served on the Board of Directors of Alibaba Group. She has been named one of Forbes' “Self Made Women”, Fast Company’s “Most Creative People in Business,”  and American Banker “Most Powerful Woman in Finance”. 

In Today's Episode with Jackie Reses We Discuss:

1. From Humble Beginnings to "Most Powerful Woman in Finance":

  • What is Jackie running from?
  • How did Jackie's upbringing impact her approach to business and management today?
  • What does jackie know now that she wishes she had known when she started her career?

2. Building the Best Teams: Lessons from Square and Yahoo

  • Why does Jackie believe that past experience is BS in hiring candidates for a role?
  • Why does Jackie deliberately not look for domain knowledge when hiring?
  • Why does Jackie believe employers should tell candidates what they suck at in hiring?
  • What does Jackie mean when she says, "you have to invest in people for 20 years"?

3. The Best Deal-Maker in the Business: Secret to Negotiating:

  • What does Jackie believe is the secret to successful negotiations?
  • How did Jackie do the Alibaba deal for Yahoo and make $50BN for them?
  • Why does Jackie believe the Laffonts and Coatue are the best risk managers?
  • What are the biggest mistakes people make in deal-making today?

4. The Next Wave of Fintech:

  • Who wins and who loses in the next wave of fintech?
  • What will happen to the crypto industry? How will crypto be regulated?
  • Why does Jackie believe that financial super apps are BS?
  • Why does Jackie believe that Goldman tried and failed to innovate?
  • Will we see a wave of M&A in fintech over the coming years?

Mar 29, 2023

Jag Duggal is the CPO @ Nubank where he is responsible for product strategy and roadmap reporting to CEO David Velez. Jag leads over 200 professionals across different functions within his role. Before Nubank, he was the Director of Product Management at Facebook, leading monetization of video and third party content. Before Facebook, Jag spent close to 7 years at Quantcast as a Senior VP of Product Management & Strategy. Finally, pre-Facebook, Jag was at Google for 5 years as a Group Product Manager and Head of Strategy (Display).

In Today's Episode with Jag Duggal We Discuss:

1. From Cushy Valley Job to CPO @ Brazilian Startup:

  • Why did Jag leave the life of luxury in the valley at Facebook to join David as CPO @ Nubank?
  • What does Jag know now that he wishes he had known when he took the position?
  • What one piece of advice would Jag give to a product leader starting a new position today?

2. Product: The Playbook, Art vs Science:

  • Why does Jag believe that product is 90% science? What is the final 10%?
  • Why does Jag believe that you should not listen to your customers?
  • What is the right way to ask customers questions to determine their pains?
  • Why does Jag believe that you should not fall in love with your own ideas?

3. Building the Bench: Hiring the Best Team:

  • How does Jag approach the hiring process for all new product hires?
  • What are the single biggest mistakes Jag has made when hiring for the product team?
  • What are the must ask questions when hiring for product?
  • What hiring lesson did Jag learn from Kevin Systrom? How has he applied it today?
  • What did Jag believe about hiring that he now no longer believes?

4. Go Time: Build, Manage and Execute:

  • Why does Jag think execution is overrated and strategy deserves more credit than people give it?
  • How does Nubank utilise small teams to operate fastest? What have been lessons here?
  • What are the best ways to do product post-mortems? What works? What does not work?
  • What has been Jag's best product decision? What has been his worst?

Mar 27, 2023

Dara Khosrowshahi is the CEO of Uber, where he has managed the company’s business in more than 70 countries around the world since 2017. Dara was previously CEO of Expedia, which he grew into one of the world’s largest online travel companies. Dara was promoted to Expedia CEO after serving as the Chief Financial Officer of IAC Travel. Before joining IAC, Dara served as Vice President of Allen & Company and spent a number of years as an analyst. He currently serves on the Board of Directors of Expedia and and was previously on the board of the New York Times Company.

In Today's Episode with Dara Khosrowshahi We Discuss:

1. From the Iranian Revolution to One of the Most Powerful CEOs:

  • What is Dara running from? What is he running towards?
  • How did seeing his family lose everything impact his mindset to life and business?
  • What are 1-2 of Dara's biggest lessons from working with the legendary Barry Diller?
  • How did Daniel Ek @ Spotify convince Dara to take the CEO role at Uber?

2. Dara Khosrowshahi: The Foundations of Great Leadership:

  • What does high performance in business mean to Dara?
  • Does Dara agree, "the best CEOs are the best resource allocators"?
  • Does Dara believe he is a better peacetime or wartime CEO? Which is he at Uber?
  • What decision-making framework does Dara use to make really hard decisions?
  • How does Dara does what to focus on and what to prioritise?

3. Investments and Acquisitions: The Scorecard:

  • Why did Dara decide to make the Kareem acquisition? Has it been successful?
  • What was the thinking behind the Postmates acquisition?
  • What does Dara believe is the single best acquisitions he has made at Uber?
  • What has been the worst acquisition he has made at Uber?
  • Why does Dara believe that Uber entering scooters was a mistake?

4. The Future: Food Delivery, Parenting, Marriage:

  • What does Dara say to those who suggest Uber Eats has lost the war to Doordash?
  • What does Dara believe is the secret to a happy marriage?
  • How does Dara define great parenting? What does Dara do to be the best father he can be?
  • What would Dara like to improve or change about himself? Why?

Mar 24, 2023

Mike Maples is one of the OGs of seed investing. As the Co-Founder of Floodgate, he has backed the likes of Twitch, Okta, Lyft, Twitter and more. Mike has been on the Forbes Midas List eight times in the last decade and was also named a “Rising Star” by FORTUNE and profiled by Harvard Business School for his lifetime contributions to entrepreneurship. 

In Today's Episode with Mike Maples We Discuss

1.) Lesson from SVB #1: The Importance of Scenario Planning:

  • What is the right way to do scenario planning in startups?
  • What is the difference between good vs bad scenario planning?
  • What do the best scenario plans include and involve?
  • What is the right way to communicate these scenario plans to your stakeholders?

2.) Lesson from SVB #2: The Importance of Financial Agility:

  • What does it mean for a startup to be "financially agile"?
  • From a banking relationships perspective, what can startups do to be financially agile?
  • How many accounts should a startup have? How much runway should be in each?
  • Should startups bank with startup banks as well as traditional banks?
  • Should startups have their money in sweep accounts and money market accounts?

3.) Lesson from SVB #3: How to Master Crisis Communications:

  • Why is it so important for founder to over-communicate in tough times?
  • How transparent should they be in these communications?
  • What does Mike mean when he says "be radically human"?
  • If Mike were to face a crisis, what would he do differently in the way he communicates to his LPs?

4.) Lessons from SVB: The Wider World:

  • Why does Mike believe the level of quantitative easing that occurred in COVID was scandalous?
  • Does Mike believe the USD will continue to be the reserve currency of the world?
  • Will we be in a better or worse macro situation by the end of the year?
  • Has Mike ever had a company that achieved true PMF and failed?

Mar 22, 2023

Frank Fillman is CRO/Country Leader Australia for Salesforce where he is responsible for responsible for the overall strategy, execution, success, and growth of the $1B+ Australian market across all industries. Prior to Salesforce, Frank was SVP/GM @ Tableau where he was responsible for the strategy, execution, and growth of Tableau's Top Accounts. Over the last 10 years at Salesforce, Frank's accomplishments include $500M+ new revenue closed in 5 years and $1B+ revenue managed. As a result, Frank has been awarded #1 Sales VP of the Year, North America, 3 times! Huge thanks to Zhenya Loginov @ Miro for the intro to Frank today.

In Today's Episode with Frank Fillman We Discuss:

1.) From Selling Kitchen Utensils to Leading $1BN Revenue Line for Salesforce:

  • How did Frank first make his way into the world of sales selling kitchen utensils?
  • Why does Frank believe, "how you handle tragedy defines you"? How did it define him?
  • What does Frank know now that he wishes he had known when he started in sales?

2.) Build and Execute the Sales Playbook:

  • How does Frank define what a "sales playbook" is today? What is it not?
  • Literally, what are the first steps to building a sales playbook? Is it the founder who does it?
  • What does a good playbook have? What does a bad playbook have? What makes the best?
  • What tools should founders and sales leaders use to create their playbook?

3.) Enterprise Deal Dynamics 101:

  • Why does Frank believe that you should never start with the price or "send over numbers"?
  • How can enterprise sellers create urgency in a deal cycle? What works? What does not work?
  • How does Frank advise sales teams on the use of discounting?
  • How open should reps be in communicating the win for them as well as the win for the customer of closing a deal?

4.) Building the Bench:

  • How does Frank structure the hiring process for all new sales reps?
  • Why does Frank believe that all sales leaders want to be super reps?
  • How does Frank rank high potential vs high experience when hiring reps?
  • What matters more; the exec have experience in the sector you are selling into or the deal size?
  • What are the single biggest mistakes founders and leaders make when hiring sales?

5.) Setting Quota and Deal Reviews:

  • How does Frank advise founders on setting quotas? Why does Q1 set the tone for the year?
  • How does Frank conduct deal reviews? How often? With who? What is the agenda?
  • What is the one question that Frank always asks when a rep says, "the client told us it was not a priority and so it slipped into next quarter"?
  • How does Frank advise founders and sales leaders on multi-threading large enterprise accounts?

Items Mentioned in Today's Episode:

Frank's Most Recent Book: The Go-Giver: A Little Story About a Powerful Business Idea


Mar 20, 2023

Bill Ackman is the CEO of Pershing Square Capital Management, L.P., an SEC-registered investment adviser founded in 2003. Pershing Square is a concentrated research-intensive fundamental value investor in long and occasionally short investments in the public markets. Bill is also a member of the board of Universal Music Group N.V. He serves as a member of the Investor Advisory Committee on Financial Markets for the Federal Reserve Bank of New York, and a member of the Board of Dean’s Advisors of the Harvard Business School. Prior to forming Pershing Square, Mr. Ackman co-founded Gotham Partners Management Co., LLC.

In Today's Episode with Bill Ackman We Discuss:

1.) From HBS to Starting Your First Fund:

  • How did Bill go from HBS to raising his first fund in Gotham Partners? How was that first fundraise?
  • From 100 meetings, what worked? What did not work? What were the core fundraising lessons?
  • What did Bill learn about great partnerships from his time with David building Gotham?

2.) Bill Ackman: A Winner's Mindset: How To Deal with the Highs and Lows:

  • On reflection, what have been the most challenging times for Bill professionally?
  • What does he say to himself when he is going through the hardest times? What is his mind talk?
  • When the war is lost and it is time for learning, how does Bill reflect and learn from losses?
  • Bill has previously described himself as "the most persistent man in America". How does Bill know when enough is enough, he was wrong and it is time to change his approach?

3.) Bill Ackman: SVB + Bank Runs and The Future of our Financial System:

  • Why does Bill believe that the depositor guarantees for SVB and Signature Bank have created a "Three Tier Banking System"? What are those three tiers?
  • Why does Bill believe that SVB is now the safest place to deposit your money? Why is First Republic Bank and SVB very different in terms of their exposure?
  • What can be done to prevent further bank runs? What should the Fed be doing? Why are they not doing it? What would Bill do if he was in charge of the Fed?
  • Why does Bill believe the current levels of FDIC insurance are insufficient and outdated? What should be used in their place?

4.) Bill Ackman: The World Around Us & Potential Politician

  • Why does Bill want Jamie Dimon to run for President? If it is Trump vs Biden, who wins?
  • Why does Bill believe Biden's tax policies destroy the US economy? What should we have instead?
  • Why does Bill believe we should give every newborn baby $6,500 and invest it for them when born?
  • What are Bill's 10-Year Long's and 10-Year Shorts? Why them?
  • Would Bill ever run for politics? When is the right time?

Mar 17, 2023

Ophelia Brown is the Founder of Blossom Capital, one of Europe's newest but leading early-stage venture firms. Ophelia and the Blossom team have invested in stand-outs including Checkout, Duffel, Tines, and Moonpay. Prior to Blossom, Ophelia was a GP at LocalGlobe and a Principal at Index Ventures where her investments included Robinhood and Typeform.

In Today's Episode with Ophelia Brown We Discuss:

1.) From Restaurant-Owning DJ to Leading European VC:

  • How Ophelia made her way into the world of venture and came to found Blossom?
  • What does Ophelia know now that she wishes she had known when she entered venture?
  • What does Ophelia feel she is running away from?

2.) Venture Capital: The Market:

  • Why does Ophelia believe the best venture firms focus either by stage/theme/geography?
  • Why does Ophelia believe that marketing in venture has no substance? How can founders determine between what is real and what is false?
  • Why does Ophelia believe that growth investors have ruined the venture market?
  • When does Ophelia believe VCs will realise that FOMO investing is not a good strategy?

3.) Ophelia Brown: The Investor and Fund Manager:

  • What has been Ophelia's biggest investing mistake? How did it change her mindset and approach?
  • In a world where everyone does seed investing, why does Ophelia not?
  • How was raising the first Blossom fund? What were some of her biggest lessons?
  • Why does Ophelia believe that follow-on investing can damage returns?
  • How does Ophelia reflect on her own relationship to price? When has she paid up and it worked? When has she paid up and it not worked?
  • Does Ophelia think it is fair that many find her curt and abrasive to work with?

4.) Europe: Is Now Really The Right Time?

  • What would Ophelia like to see change in the way European VCs act?
  • If Ophelia could invest in one seed firm, one Series A firm and one growth firm in Europe, what would they be? Why?
  • What are 1-2 of the biggest barriers Europe must overcome in the next 5 years?

Mar 15, 2023

Adam Grenier is an OG of the growth world. His first role in growth, was none other than Uber where he was Head of Growth Marketing and Innovation building the global marketing growth infrastructure and team from the ground up. He then enjoyed successful spells at Lambda School and Masterclass as VP Growth and VP of Marketing, respectively. If that was not enough, Adam is also a prolific angel having made investments in Superhuman, Table22, and FitXR to name a few.

In Today's Episode with Adam Grenier We Discuss:

1.) Entry into the World of Growth with Uber:

  • How did Adam make his way into the world of growth with Uber and Ed Baker?
  • What are the single biggest takeaways from his time at Uber, Lambda and Masterclass?
  • What does Adam know now that he wishes he had known when he started in growth?

2.) Growth: What it is? Why You Do Not Need a Team for it?

  • How does Adam define the term "growth" today? What is the role of "Head of Growth"?
  • Why does Adam believe that you do not need a growth team?
  • How can leaders infuse growth principles, mindsets and metrics into existing teams?
  • WHat are the single biggest mistakes founders make when thinking about growth?

3.) Hiring Growth Mindsets: How to Ask the Right Question:

  • What are the clearest signs to Adam that someone has a growth mindset?
  • What are the right questions to ask to see how they think?
  • How does Adam use tests and case studies to determine the growth mindset of a person?
  • What did Uber teach Adam about the best practices to hire for growth?

4.) Uber: Scaling a Monster and Spending $1BN on Ads:

  • What are some of Adam's biggest lessons from spending $1BN on advertising at Uber?
  • Why at anytime were there 200 people paying for ads with their personal credit cards?
  • Why does Adam believe China was "the wild-west"? How did all of their competitors in China have Uber data?
  • How do growth mechanics, channels and disciplines compare between US vs China?

Mar 12, 2023

Jackie Reses is the CEO of Lead Bank and previous Exec Chair of Square Financial Services and Head of Lending and Banking. One of only people to have started a bank as a de no; Only tech company to get approved for a de novo. Chair Economic Advisory Council of SF Federal Reserve. 

Kris Dickson is the CFO of Lead Bank and previously the CAO / CFO of post-BK Lehman Brothers parent co-estate for 10 years. Lehman Holdco estate has liquidated and distributed $129 billion to unsecured creditors through the end of 2022.

In Today's Episode on SVB We Discuss:

What Happened?

  1. How and why did SVB fail so fast?
  2. Was it the result of systemic problems or a series of management mistakes?
  3. What role did VCs play in the downfall of SVB?
  4. What role did social media and online banking play in the failing of SVB?

What Now?

  1. What happens now?
  2. Will depositors have their deposits guaranteed?
  3. Will there be a buyer for SVB? Who is the most likely?
  4. Should founders be worried about moving their money to neo-banks?
  5. Should founders in any circumstances transfer money to their personal accounts?
  6. What is the best and worst outcome?

Mar 10, 2023

Amjad Masad is the Founder and CEO @ Replit, whose mission is to bring the next billion software creators online. With Replit, Amjad has raised over $100M from the likes of Peter Thiel, a16z, Coatue and Addition, to name a few. Before founding Replit, Amjad was a tech lead on the JavaScript infrastructure team at Facebook. Before Facebook, Amjad was #1 employee at Codecademy.

In Today's Episode with Amjad Masad We Discuss:

1.) From Troublemaker Child in Iran to Silicon Valley Founder:

  • How did Amjad make his way into the world of tech and Silicon Valley having grown up as a misbehaving child in Iran?
  • In what ways did Amjad show early signs of exceptionalism? Why does he always look for this in people he is hiring for Replit?
  • What does Amjad know now that he wishes he had known when he started Replit?

2.) The Future: A New World with AI at the Centre:

  • Why does Amjad believe we will see thousands of billionaires created from the innovation in AI?
  • Why does Amjad believe AI will lead to 100 more Elon Musks?
  • If Amjad were CEO of Facebook, what would he do? Why and how do they have to invest in AI?
  • Will TikTok be banned in the US? How will this be resolved?
  • Why does Amjad believe that 300 people control the future of AI? Is that not concerning?

3.) The Future of Society, Employment and Wages:

  • Why does Amjad believe in 10 years, 1 engineer will be able to do what 100 do today?
  • What will happen to the real wages of engineers?
  • How does Amjad see the inclusion of universal basic income in the future?
  • Is Amjad concerned about societal and civil unrest with wealth disparity widening further?

4.) Building the Replit Army:

  • Why does Amjad believe that so many in tech have gotten too soft in the last few years?
  • Why does Amjad release a "Why You Should Not Join Replit" page and share it with all candidates?
  • How can a founder know if they have good company values or not?
  • Why does Amjad feel we need a spiritual reform in company building? Why are startups and religion the same?

Mar 8, 2023

Glen Coates is the VP of Product @ Shopify, leading the development of Shopify’s core commerce platform. He also oversees the core developer platform and Shopify’s partner ecosystem, which includes over 10,000 publicly available apps in the Shopify App Store. Originally a CompSci grad, Glen moved from Sydney to San Diego in 2008 to run US distribution and e-commerce for an Australian eco-products company. In 2010, he attended Columbia Business School for one whole day before quitting to start Handshake, a SaaS B2B e-commerce platform. Glen joined Shopify in May 2019 when the company acquired Handshake. Glen has been in the Vice President role since October 2020.

In Today's Episode with Glen Coates We Discuss:

1. From Game Developer in Sydney to Running E-Commerce Warehouse in NYC:

  • How Glen made his way into the world of product and e-commerce having started life as a game developer?
  • Why does Glen believe that the best founders and product people often have their roots in gaming?
  • What does Glen know now that he wishes he had known when he joined Shopify?

2. The Art of Product and Product Management:

  • Is product more an art or a science? If you had to put a number on it, what would it be?
  • What is "product management"? Why can it not be reduced to frameworks?
  • What are "product principles"? How do Shopify use them? How should product teams set them?
  • What makes the very best PMs today? What are the commonalities in them?
  • What is the sign of a poor PM? What would Glen most like to change about the world of PMs?

3. The Art of Product Marketing:

  • What does Glen believe is the true art of product marketing?
  • How did a CEO group teach Glen how to tell truly great stories?
  • How can one tell great stories when you have to cater to multiple different customers/personas?
  • How does Glen evaluate the current state of Shopify's product marketing?

4. Shopify and The Future of Shopify:

  • Why does Glen think it is important for Shopify to have a tops down decision-making process for product strategy?
  • What does Glen believe is the #1 reason why Shopify is such a large and successful company?
  • What is the single hardest element of Glen's role today?
  • How does Glen believe that Shopify will be larger than Amazon in 5-10 years time?

Mar 6, 2023

Alex Schultz is the Chief Marketing Officer and VP of Analytics for Meta (formerly Facebook), leading Marketing, Analytics, and Internationalization. Previously, Mark Zuckerberg stood up and said, "Facebook would not be a BN user company without Alex". At Meta, Alex has pioneered the integration of product and direct response marketing at Meta and helped launch many of the company’s most impactful products and initiatives. Alex is gay and is the executive sponsor of Facebook’s LGBTQ+ Employee Resource Group.

In Today's Episode with Alex Schultz We Discuss:

1. From Paper Planes to CMO of Facebook:

  • How Alex started his career in the world of paper planes and how that led to his getting a role at an early eBay? What are 1-2 of his biggest lessons from eBay?
  • How did the role at Facebook come about in 2008? Why did he decide to join the early Facebook?
  • What does Alex know now that he wishes he had known when he started his time at Facebook?

2. The Secret to Scaling to 1 Billion Users:

  • Mark Zuckerberg has said that "Facebook would not be a billion-user company without Alex". So what does Alex believe are the 1-2 biggest needle movers in FB scaling to 1 billion users?
  • Why does Alex believe that the best leaders are patiently right?
  • How can management be direct and effective but also show they care and be kind?
  • What have been some of Alex's biggest lessons on people management across different phases of the company?

3. Crucible Moments in Facebook History:

Facebook Messenger Split:

  • What was the decision-making process behind splitting Messenger from the core Facebook App?
  • What did they do right and well in the split? What mistakes were made?

Rebrand to Meta:

  • Why did Facebook decide it was right to rebrand to Meta?
  • Has the rebrand gone well? How does Alex define success with the rebrand?

Reels vs TikTok vs SNAP:

  • Does Alex believe we are moving away from the social graph and moving to content discovery only?
  • How does Alex feel Reels is doing in the race against TikTok? What have they done well?
  • Why does Alex believe SNAP hasn't innovated in the way people think and copied Kakao in cases?
  • What is the key to turning Reels into a monetization machine for Facebook?

4. Alex Schultz: The Person and Leader:

  • How was the coming out process for Alex in the tech community?
  • How did his parents respond to the news? What does Alex mean when he says, "everyone has to mourn their own version of your future self"?
  • Why when he moved to the states was Alex advised to go back in the closet?
  • Does Alex feel we have a long way to go in equalizing the playing field both for homosexuality and trans-gender participation?

Mar 3, 2023

Hunter Somerville is a Partner @ Stepstone, one of the largest secondary buyers, fund investors and players in our ecosystem with over $600BN in capital responsibility and over $100BN AUM. Additionally, Hunter serves on the LP Advisory Boards for Felix Capital, Foundry Group, Imaginary Ventures, Scale Venture Partners, Boldstart Ventures, Ludlow Ventures, and more. Prior to StepStone, Hunter was a general partner with Greenspring Associates, a venture capital and growth equity investment firm that merged with StepStone in 2021. Before that, he worked as an associate for Camden Private Capital.

In Todays Episode with Hunter Somerville We Discuss:

1. Three Types of Secondaries:

  • What are the three different types of secondaries?
  • What is the current situation with company secondary opportunities today?
  • What is the current landscape for fund secondary opportunities today?
  • What are GP-led restructuring or strip sales? How do they work?

2. LPs Today and Moving Forward Investing in Funds:

  • Will we see a wave of LPs not commit to their existing managers?
  • What is the denominator effect and how does that impact LP deployment into funds?
  • What are the top 3 reasons why LPs will not re-commit to existing managers?
  • Do LPs feel VCs have fairly marked down their venture books in the last 6 months?
  • Does Hunter agree that if you have not returned cash to your LPs when you could have done ijn the last 5 years, then you are most in trouble?
  • Why does Hunter believe we will see more international LPs entering venture than ever before?

3. Liquidity: When Does the Cash Hit:

  • Why was liquidity so bad in 2022? How did that compare to 2021?
  • How does Hunter forecast liquidity environments in 2023? What could drive them?
  • How active were Stepstone in secondary buying over the last few years?
  • Is now the time to be greedy when others are fearful in secondaries?
  • What discount was Hunter seeing both on fund and company side secondaries in 20-22?
  • What is the current level of discount being applied to both company and fund secondaries?

4. AMA with One of the Largest Secondary Buyers:

  • Which LP class will be hurt the most from the last fund cycle?
  • What would Hunter most like to change about the world of venture?
  • What was Hunter's biggest mistake on a company investment?
  • What are the biggest mistakes LPs make when they do direct investing?
  • Why are big-name people entering firms as GPs not always a good sign?

Mar 1, 2023

Jamie Siminoff is the Founder and Chief Inventor @ Ring, with Ring Jamie, created the world’s first Wi-Fi video doorbell while working in his garage in 2011. Since Ring’s launch in 2013, Ring has helped make thousands of neighborhoods safer all around the world. As part of the journey, Jamie raised over $385M from the likes of True Ventures, Felicis, First Round, CRV, Upfront and more. In 2018, Amazon acquired Ring for a reported $1BN. Prior to Ring, Jamie founded several successful ventures including PhoneTag, the world’s first voicemail-to-text company, and, a service that helped email users clean commercial email from their inboxes. He successfully sold both companies in 2009 and 2011 respectively.

In Today's Episode with Jamie Siminoff We Discuss:

1.) From Creating the First Wi-Fi Doorbell to $BN Acquisition:

  • When was the moment Jamie realized he had to create the world's first Wi-Fi-enabled doorbell?
  • How di Richard Branson come to be an investor in Ring? What was the process?
  • How does Jamie advise other founders when it comes to the question of whether it is valuable having business moguls as investors in their business?

2.) Crucible Moments: From Lawsuits and Near-Death to $22M in Sales in a Day:

  • When Jamie hears the words "near-death experience" what is the moment in the Ring journey that comes to mind?
  • How did Jamie get through a crippling lawsuit and come out selling $22M in 24 hours on QVC?
  • How did Jamie feel when he placed a $500M order with manufacturers when he only had $100M?
  • What does Jamie believe was the hardest phase of the business?

3.) Jamie Siminoff: The Leader:

  • Why does Jamie want to hire marathon runners? Why does the analogy make for good hires?
  • Does Jamie start from a position of trust with new hires and it is there to be built or start with no trust and it is there to be gained?
  • Does Jamie believe he is a tolerant leader? What does he mean when he says, "I want to see the dirt under your fingernails"?
  • Why does Jamie believe that building a brand is like making great wine?
  • Why does Jamie really hate customer surveys? What should be done instead?

4.) Selling for $1BN to Amazon:

  • How did the Amazon acquisition come to be? How did the discussion go?
  • Why did Jamie decide then was the right time?
  • When you sell for a $1BN, does the cash hit your account soon? When did Jamie actually receive the money? How did he feel when he saw it is in his account?
  • What does Jamie believe Ring did so well to make the acquisition a success?
  • What did Amazon do well to ensure Ring was integrated most effectively?
  • What are 1-2 of the biggest lessons Jamie has learned from being within Amazon?