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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 www.20vc.com for more information on the podcast, show notes, resources and more.
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Now displaying: 2023
Aug 25, 2023

Howie Liu is the Founder and CEO @ Airtable, the fastest way to build apps for your business. To date, Howie has raised over $1BN with Airtable with the last round valuing the company at $11BN and an investor base including Benchmark, Thrive, Caffeinated, Greenoaks and Coatue to name a few.

In Todays Episode with Howie Liu We Discuss:

1. Scaling into Enterprise:

  • What are the single biggest challenges when moving from PLG to enterprise?
  • Why does Howie believe you have only truly hit enterprise when you sign $1M contracts?
  • How long did it take for Airtable to sign their first $1M ARR contract?
  • How can founders know when is the right time to scale into enterprise?
  • How does the product need to change with the scaling?

2. Enterprises: Do They Really Love AI:

  • Why does Howie believe that enterprises are not jumping on AI yet?
  • When does enterprise interest turn into enterprise buying and purchasing?
  • What are the single biggest barriers to enterprises buying AI solutions today?
  • Post-purchase, what are the biggest implementation challenges for enterprises with AI?

3. The Changing Sales Process:

  • Are we seeing the bundling of tools within large enterprises today?
  • Which categories and vendors are most vulnerable? Which will survive the cuts?
  • What do vendors need to do to prove to CFOs that they need to remain in their budget?
  • How has the customer success process changed over the last year with tightening budgets?

4. Howie Liu: AMA:

  • Airtable famously got Benchmark to lead their Series C, how did this come to be when they famously always only do Series A?
  • Why does Howie believe that it is total BS to suggest post-PMF, everything is good?
  • What does Howie know now that he wishes he had known when he started Airtable?

Aug 23, 2023

Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product.

Rick Zullo is the Co-Founder and General Partner at Equal Ventures. Prior to co-founding Equal Ventures, Rick was an investor at Lightbank, Prior to Lightbank, Rick worked with investment firms Foundation Capital, Bowery Capital, and Lightview Capital.

In Today's Episode We Discuss:

1. Why Venture Capital Needs It's Jerry Maguire Moment:

  • Why does Rick believe that VC needs it's "Jerry Maguire" moment?
  • What needs to change? What needs to stay the same?
  • Why does Jason believe we will see even more mega funds in 2024 and 2025?

2. Unicorns are So 2019:

  • Why does Jason believe that "unicorn investing is mostly dead for bigger funds and none of them are looking for a $1BN outcome anymore?"
  • Why does Rick believe that multi-stage fund investing at seed simply does not make sense?
  • What does Rick believe many founders need to know when they take multi-stage money at seed?
  • Of the over 1,000 unicorns created over the last few years, how many of them do Rick and Jason feel are actually unicorns today?

3. Efficiency and Growth: We Need it All:

  • Why does Jason believe, as a founder you should be embarrassed if you ever had a RIF (reduction in force)?
  • Last year many founders got a pass on growth as they were more efficient. Is that pass over? Do they need to get back to growth?
  • What is the single biggest reason that companies do not scale from seed to Series A?
  • What happens to the many companies with years of runway but no product-market-fit?
  • Are we entering a new age of efficient company building or will we go back to high burn environments and excessive spending?

4. Entering the World of LPs:

  • If Jason and Rick were to advise LPs today on how much to discount the value of their venture books, what advice would they give?
  • How have markups completely corrupted the venture ecosystem?
  • How does LPs being incentivized by paper-marks make the industry even more screwed?
  • What are the single biggest misalignments between GP and LP?

Aug 21, 2023

Nick Huber is a serial entrepreneur, investor, and content creator focused on real estate and small business. In the last 9 months, Nick has co-founded 6 companies including RE Cost Set, RecruitJet, Titan Risk, Blue Key Capital, Tax Credit Hunter, and WebRun Labs. His primary business, Bolt Storage, owns 1.8M sqft of self-storage facilities across 62 locations in 11 states. 

In Todays Episode with Nick Huber We Discuss:

Wealth:

  1. What the richest families in the world all understand and what the majority of people forget?
  2. What are the two best ways to make money as an employee? What do most forget/not do?
  3. Why money does make you happy and why society drastically undervalues wealth today?
  4. Why we should not be concerned by the levels of income inequality?

Marriage and Parenting:

5. Why it is BS to not pass your wealth down to your children?
6. Why you have to let your kids suffer in order for them to grow?
7. How do you stop kids from becoming assholes if they are brought up with money?
8. Why the majority of the time, people choose the wrong partner? What should we look for?
9. What is the number one thing you can do to set your child up for success?

Silicon Valley and Entrepreneurship:

10. Why entrepreneurship is not for everyone? Who is it for?

11. Why VCs are out of touch and naive?

12. What is the single biggest lie of Silicon Valley?

13. Why will so many would-be great entrepreneurs burn themselves out when they should not have to?

Management and Brand Building:

14. How to build a brand today? Why you have to be controversial to be interesting?

15. How to deal with hate and criticism? Why you cannot please everybody?

16. Why woke culture can give you an advantage if you do not have it?

17. How to build a strategic network the right way? How to become a card in someone's rolodex?

18. What is the single worst thing you can do when hiring?

19. What do you do when you lose trust in an employee?

 

Aug 18, 2023

Richard Socher is the founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of AI startup MetaMind, acquired by Salesforce in 2016. He is widely recognized as having brought neural networks into the field of natural language processing, inventing the most widely used word vectors, contextual vectors and prompt engineering. He has over 150,000 citations and served as an adjunct professor in the computer science department at Stanford.

In Today's Episode with Richard Socher We Discuss:

1. The Decade-Long Journey to Becoming an AI OG:

  • How did Richard first make his way into the world of AI over a decade ago?
  • What are 1-2 of his biggest lessons from working with Marc Benioff?
  • How did 5 years at Salesforce impact how he both thinks and operates?

2. Models: Does Size Matter:

  • How important is model size? Is data size more important?
  • What are the biggest misconceptions people have around models today?
  • How does Richard respond to the suggestion that "many startups are wrappers around LLMs"?
  • Are hallucinations a feature or a bug?

3. Where Does Value Accrue:

  • Where does Richard believe most of the value will accrue; startup or incumbent?
  • Which incumbents are best positioned to win? Which are the laggards and behind?
  • What do many not see about the startup vs incumbent race in the AI war?

4. Open vs Closed: Which Wins:

  • Does Richard favour Yann LeCun's open approach? Or is the world of AI more closed?
  • What are the biggest challenges of an open ecosystem?
  • What are the nuances that make both challenging?

5. Richard Socher: AMA:

  • Why will carpenters be paid more than software engineers in 10 years?
  • Why is AGI still way off? Are people too unrealistic?
  • How much money does Google make off search every day? Why does that leave them vulnerable?

Aug 16, 2023

Brian Balfour is the Founder and CEO of Reforge. Previously, he was the VP of Growth @ HubSpot. Prior to HubSpot, he was an EIR @ Trinity Ventures and founder of Boundless Learning and Viximo. He advises companies including Blue Bottle Coffee, Gametime, Lumoid, GrabCAD, and Help Scout on growth and customer acquisition.

In Today's Episode with Brian Balfour We Discuss:

1. Entry into Growth and Lessons from Hubspot:

  • How did Brian make his entry into the world of growth?
  • What does Brian know now about growth that he wishes he had known when he started in growth?
  • What are 1-2 of his single biggest takeaways from his time at Hubspot that impacted his mindset?

2. The Foundations:

  • What is growth? What is it not?
  • What does Brian mean when he says "all growth can be boiled down to 4 things"?
  • When is the right time to bring in your first growth person?
  • Should the first growth person be senior or junior?
  • Should the growth team be standalone or sit within an existing function?

3. The Importance of Product Channel Fit:

  • What is product channel fit? How should founders approach it?
  • How do you know when you have it?
  • What are the single biggest mistakes founders make with regards to PCF?

4. Next Comes Channel Model Fit:

  • What is channel model fit? How should founders approach it?
  • What are clear indicators that you have or do not have channel model fit?
  • What are the biggest mistakes founders make with CMF?

5. Finally, Model Market Fit:

  • What is model market fit? How should founders approach it?
  • What are clear indicators that you have or do not have model market fit?
  • What are the biggest mistakes founders make with MMF?

6. Brian Balfour: AMA:

  • Why is product market fit not enough?
  • What does Brian mean when he says "revenue does not create usage"?
  • What are the biggest dangers of mixing customers and users?
  • What do Hubspot do better than anyone else to know when an existing product/strategy is dying?
  • Is it always better to diversify marketing channels?

Aug 14, 2023

Tim Urban is the writer/illustrator and co-founder of Wait But Why, a long-form, stick-figure-illustrated website with over 600,000 subscribers and a monthly average of half a million visitors. He has produced dozens of viral articles on a wide range of topics, from artificial intelligence to social anxiety to humans becoming a multi-planetary species. Tim’s 2016 TED main stage talk is the third most-watched TED talk in history with 66 million views. In 2023, Tim published his bestselling book What’s Our Problem? A Self Help Book for Societies.

In Today's Episode with Tim Urban We Discuss:

1. The Founding of Wait by Why:

  • What was the a-ha moment for Tim that Wait but Why should be his life's work and sole focus?
  • What does Tim know now that he wishes he had known when he started?
  • What does Tim believe he is running away from? Why is he so fearful of constraints?

2. Wait But Why: The Scaling Journey to 600,000 Subs:

  • What was the first piece to really go viral? How did that change the trajectory?
  • What single piece is Tim most proud of? What piece is he least proud of?
  • What has been the hardest element of scaling Wait But Why?
  • What was the most surprising and unexpected elements of Wait But Why's scaling?

3. Topic Selection: Choosing What To Write:

  • What does the process look like for Tim when deciding what topic to write about?
  • How does Tim know what his audience will want to hear about vs what they will not?
  • What topics has Tim thought would be interesting but post initial research, are not?

4. The Writing Process:

  • How does Tim approach the writing process? How has his changed over time?
  • What mechanisms does Tim put in place to avoid writers block?
  • What are some of Tim's biggest tips to aspiring writers and authors?

5. The Distribution Process:

  • How does Tim approach distributing the content once produced? What works? What does not?
  • Why did Tim choose newsletter, Twitter and Instagram as his channels of choice?
  • How important has the newsletter been to the growth of the business?

6. AI: Super-Intelligence and The Future:

  • On reviewing his pieces on AI back in 2015, what does he believe he got right? What would he change with the benefit of hindsight?
  • Is Tim more or less positive looking forward at AI proliferating through all of society?
  • What is Tim most concerned about in the world right now?

Aug 11, 2023

Sam Lessin is a Co-Founder and Partner @ Slow Ventures with a portfolio including the likes of Airtable, Robinhood, Slack, Solana, PillPack and many more unicorn companies. Prior to Slow, Sam was a VP Product at Facebook having sold his company to Meta.

Frank Rotman is a founding partner of QED Investors, one of the leading fintech-focused venture firms investing today with a portfolio including the likes of Klarna, Kavak, Quinto Andar, Credit Karma and more. As for Frank, prior to QED, Frank was one of the earliest analysts hired into Capital One and spent almost 13 years there helping build many of the company’s business units and operational areas. 

Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product.

In Today's Discussion on Why Seed is Broken We Discuss:

1. The Seed Model Was Broken and What Comes Now:

  • Why does Sam Lessin believe the model for seed of a "factory line" was broken?
  • What does he believe will replace it?
  • Why does Jason Lemkin argue that this might not be the case for SaaS and enterprise?

2. Round Construction: YC, Multi-Stage Funds and Party Rounds:

  • Why does Sam Lessin believe we have seen the end of party rounds? Why does Jason Lemkin disagree and we will see more than ever?
  • Why does Sam Lessin believe the factory model of YC churning out companies is over? Where does Jason Lemkin believe the value lies in the YC model?
  • Will the multi-stage funds remain in seed? How has their entrance and deployment changed the seed market?

3. VC Value Add at Seed: Is it BS?

  • Why does Jason believe all talent arms in venture firms have failed?
  • Why does Sam believe that no VCs provide value?
  • Do the best founders really need help? Why do Jason and Sam disagree?

4. What Happens Now:

  • Why does Jason believe that every manager can write off their fund from 2021?
  • Who will be the winners in seed in the next 10 years?
  • Why does Sam believe if you want to bet on AI, just bet on Meta or Microsoft?
  • What will happen to the many companies with no PMF but 10 years of runway?

Aug 9, 2023

Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product.

In Today's Episode with Jason Lemkin We Discuss:

1. WTF is Happening At Seed Right Now:

  • Why does Jason believe seed is more active than ever?
  • Is the pricing of seed rounds impacted since the downturn?
  • Why does Jason believe it is not only not the end of party rounds but just the beginning of them?
  • Why does Jason believe you cannot fail if you have $1M in ARR and an amazing founder?
  • Why does Jason believe that seed investors cannot participate in "hot seed rounds" anymore?

2. Is Series A a Dead Zone:

  • How does Jason analyze the Series A and B environment today?
  • What has changed in what investors expect and want to see in potential Series A and B investments?
  • What happens to the many companies who raised pre-emptive Series As and have 10 years of runway but no product-market fit?
  • Why does Jason believe founders should offer to give the money back when it is not working?
  • What happens to the Series A and B market in the next 18 months? When does it come back?

3. Growth: People are Too Negative!

  • Why does Jason believe that growth is more active than many are giving credit for?
  • What are the ARR benchmarks required to get a good growth round term sheet today?
  • Why does Jason believe that VC DD is a load of BS?
  • Why does Jason believe that every VC has fraud in their portfolio? Will they come out?

4. Ring That Bell: IPOs and M&A:

  • Why does Jason believe 2024 will be an amazing year for IPOs?
  • Why does much of the IPO market rely on Stripe and Databricks?
  • What is needed for an amazing 2024 IPO market?
  • How does Jason evaluate the M&A market in 2024? Will regulation get in the way?

5. Jason Lemkin: AMA:

  • Why does Jason Lemkin believe this generation of workers will never work hard again?
  • What is the only way for seed funds to make money investing in serial entrepreneurs?
  • What does Jason know now that he wishes he had known when he started investing?

Aug 7, 2023

Vinod Khosla is the Founder of Khosla Ventures, one of the leading venture firms of the last decade with investments in OpenAI, Stripe, DoorDash, Commonwealth Fusion Systems and many more. Prior to founding Khosla, Vinod was a co-founder of Daisy Systems and founding CEO of Sun Microsystems.

In Today's Episode with Vinod Khosla We Discuss:

1. The State of AI Today:

  • Does Vinod believe we are in a bubble or is the excitement justified based on technological development?
  • What are the single biggest lessons that Vinod has from prior bubbles?
  • What is different about this time? What is Vinod concerned about with this AI bubble?

2. The Future of Healthcare and Music:

  • How does Vinod evaluate the impact AI will have on the future of healthcare?
  • How does Vinod analyse the impact AI will have on the future of music and content creation?
  • Does Vinod believe that humans will resist these advancements?
  • Who will be the laggards, slow to embrace it and who will be the early adopters?

3. Solving Income Inequality:

  • Does Vinod believe AI does more to harm or to hurt income inequality?
  • What mechanisms can be put in place to ensure that AI does not further concentrate wealth into the hands of the few?
  • Does Vinod believe in universal basic income? What does everyone get wrong with UBI?

4. The Future of Energy, Climate and Politics:

  • Why is forcing non-economic solutions the wrong approach to climate? What is the right approach?
  • Why is Vinod so bullish on fusion and geothermal? How does fusion bankrupt entire industries?
  • How does the advancements in energy and resource creation change global politics?
  • Does Vinod believe Larry Summers was right; "China is a prison, Japan is a nursing home and Europe is a museum"?

5. Vinod Khosla: AMA:

  • What is Vinod's single biggest investing miss?
  • What does Vinod know now that he wishes he had known when he started investing?
  • Why did the Taylor Swift concert have such a profound impact on him?
  • What was Marc Andreesen like when he backed him with Netscape in 1996?

Aug 4, 2023

Ilir Sela is the Founder and CEO of Slice, the all-in-one ordering and marketing tech platform for local pizzerias. Through its partnerships, Slice has driven over $1B in earnings for over 18,000 independent pizzerias nationwide. Fun fact, Slice is also one of the largest employers in Macedonia and at one point, employed so many people there, they had to start their own school to train more people. Before Slice, Ilir started Nerd Force and sold it in 2008. Huge thanks to Jeff Richards (GGV) and Ben Sun (Primary) for some amazing questions today.

In Today's Discussion with Ilir Sela We Discuss:

1. From Macedonia to the Bright Lights of NYC and Bentley Buying:

  • How Ilir made his way into the world of startups having grown up in Macedonia?
  • How did his less affluent upbringing impact his approach to company building?
  • How does Ilir think about the importance of money? How did he come to buy a Bentley?
  • What does Ilir know now that he wishes he had known when he started?

2. Why Bootstrapped Was Best & The Decision to Fundraise:

  • Why did Ilir scale the business to $4M in revenue without ever fundraising?
  • What does Ilir believe are the benefits of scaling businesses with less money?
  • What would Ilir have done differently had he raised money earlier?
  • What advice does Ilir have for founders who see competitors raising more money than them?

3. Why Delegation is BS and Your Upbringing F***** You Up:

  • Why does Ilir believe that much of our upbringing can instill principles which make us a worse leader?
  • Why does Ilir believe it is BS to hire great people and get out of the way?
  • What are the single biggest mistakes Ilir sees founders make in company scaling?
  • What have been some of Ilir's biggest lessons in talent acquisition?

4. Decision-Making 101:

  • How does Ilir analyze his decision-making framework today?
  • Where does he need to improve as a leader today? What does he need to do to get there?
  • What has been the single best decision he made with Slice? What did he learn from it?
  • What has been the worst decision he has made in the scaling process? How did that change his mindset?

Aug 2, 2023

Lori Jimenez is the Chief Revenue Officer at WorkRamp where she is responsible for sales, customer success, solutions engineering, sales development, and revenue operations. Over her 25-year career, Lori has a track record of scaling high-growth GTM teams at companies including Google, TripActions/Navan, Facebook, and Box.

In Today's Episode with Lori Jimenez We Discuss:

1. From a First Sales Job at 15 Years Old to Leading Sales Teams at Google and Facebook:

  • How Lori made her foray into the world of sales at the age of 15?
  • What are 1-2 of Lori's biggest takeaways from her time at Google, Facebook and Box?
  • What does Lori know now that she wishes she had known at the start of her career in sales?

2. The Sales Playbook: What, When and How:

  • How does Lori define the "sales playbook"? What is it not?
  • Should the founder be the one to create the sales playbook?
  • When is the right time for founders to make their first sales hires?
  • What is the right profile for the first sales hires?
  • Should founders hire 2 sales reps at a time? What are the pros and cons?

3. The Hiring Process: Building the Sales Team:

  • How does Lori structure the hiring process for all new sales hires?
  • What are the must-ask questions to ask in every sales hiring meeting?
  • What are the biggest red flags founders should look for when hiring for sales?
  • What are Lori's biggest lessons on how to navigate compensation discussions with potential sales hires?
  • What are Lori's biggest lessons on what title negotiation says about a candidate?
  • What are the single biggest mistakes founders make when hiring for sales teams?

4. Scaling the Machine: Bringing the Dollars In:

  • How does Lori approach discounting? When is the right time to do it?
  • Is old-school enterprise sales and entertaining dead? How has it changed?
  • How does Lori structure deal reviews? What is a good vs a bad reason to lose a deal?
  • How does Lori approach multi-year deals? What is good? What is bad?

Jul 31, 2023

Marcelo Claure is the Founder & CEO of Claure Group, a multi-billion-dollar global investment firm. He is the Executive Chairman and Managing Partner of Bicycle Capital, a $500M Latin America-focused growth equity fund, and was appointed Chairman in Latin America of SHEIN, the global #1 on-demand fashion company in the world. Claure was also the CEO of SoftBank Group International where he launched SoftBank’s $8B Latin America Funds, and had direct oversight for SoftBank's operating companies. As an entrepreneur, Marcelo built Brightstar from a small local distributor to the world’s largest global wireless distribution and services company. In addition, Claure led the turnaround of US wireless telecommunications company Sprint and helped orchestrate its US$195 billion merger with T-Mobile.

Shu Nyatta is the founder of Bicycle Capital. Before Bicycle, Shu was most recently a Managing Partner at SoftBank Group International, where he launched and managed two separate funds - the SoftBank Latin America Fund and the Opportunity Fund for early-stage investments in US-based founders-of-color. In the first part of his SoftBank career, Shu was a founding Partner of SoftBank's Vision Fund. Several companies have retained him on their boards as an independent board member following his departure from SoftBank, including Lemonade (NYSE: LMND), Kavak and Tribal Credit. Shu also serves on the board of Endeavor Global - the leading global community of, by and for high-impact entrepreneurs.

In Today's Episode Featuring Bicycle Capital We Discuss:

1. From Deploying $10BN at Softbank to Founding Bicycle Capital:

  • What was the founding moment for Marcelo and Shu in the founding of Bicycle?
  • What does Shu believe is Marcelo's superpower? How has working with Marcelo changed the way he thinks?
  • Why does Marcelo believe that he is not a good investor? How does Shu make him better, specifically?

2. Lessons from Investing $10BN at Softbank:

  • What are 1-2 of the biggest lessons from investing $10BN over the last few years at Softbank?
  • How did missing OpenAI and Nubank impact how Shu and Marcelo think and invest today?
  • Why was losing $150M on Softbank's FTX investment, the biggest lesson of Marcelo's career?
  • What are Marcelo and Shu doing differently at Bicycle, having seen how it went at Softbank?

3. The Venture World is Changing:

  • Why do Marcelo and Shu believe the world of venture is changing? How is it changing most?
  • Why are founders going directly to LPs to raise rounds today, over going to VCs?
  • Do Marcelo and Shu believe that many VCs provide value?
  • Who will win in the next 10 years of venture? Who will lose?
  • Why do Marcelo and Shu believe you should not invest in founders that do not take your advice?
  • Do Marcelo and Shu agree with the statement that "the best founders do not need your help"?

4. LATAM is Under Construction: It is Time to Build:

  • What are the two reasons that the next decade will be the best ever for LATAM?
  • What are the biggest misconceptions about the LATAM tech market?
  • How do Marcelo and Shu answer the question of the lack of liquidity available with few M&A deals taking place and very few LATAM companies listing on the NASDAQ?
  • How do Marcelo and Shu evaluate the withdrawal of foreign capital from LATAM tech markets? Is it good or bad? Have a load of US funds lost money on early-stage LATAM deals?

Jul 28, 2023

Stephane Kurgan is widely considered one of the best operators in Europe. During his tenure as COO @ King, King went from $65m to $2.4B in bookings, from 100 to 2,400 employees, and did a $7B IPO before being acquired by Activision Blizzard. Prior to joining King, Stephane served as CFO of Tideway Ltd. (acquired by BMC Software) and was the co-founder and CEO of Digital Reserve. Today, Stephane serves as a Venture Partner at Index Ventures, one of the leading venture firms of the last decade and more recently as an executive advisor at Technology Crossover Ventures.

In Today's Episode with Stephane Kurgan We Discuss:

1. From Belgium Boy to Europe's Leading Operator:

  • How a CD Rom company was the starting place for one of Europe's best executives?
  • What does Steph believe he is running away from?
  • What does Steph know now that he wishes he had known when he started?

2. Four Criteria of Truly Great Leaders:

  • What four traits do all truly special leaders have?
  • What are the 1-2 that are the hardest to find in great leaders today?
  • Why does Steph believe that even the best leaders are wrong 40% of the time?
  • How does Steph approach decision-making? How has it changed over time?
  • What is the most toxic element of decisions within companies today?
  • When does Steph change plan because a decision is wrong vs stick to it?

3. Speed of Execution and Mission Statements:

  • How important does Steph believe speed of execution is today?
  • What are the elements that one can go fast on vs go slow and be very deliberate on?
  • What elements has Steph gone fast on in the past that led to a mistake? How would he have changed his approach with the benefit of hindsight?
  • Why does Steph believe that mission statements have different value at different company stages?
  • What is Steph's biggest advice to founders on creating mission statements?

4. Delivering Feedback and Maintaining Trust:

  • What are 1-2 of Steph's biggest lessons when it comes to delivering feedback well?
  • What are the biggest mistakes founders make when delivering feedback today?
  • Can trust be regained once lost? How?
  • Does Steph start from a position of full trust or is it gained gradually over time?

Jul 26, 2023

Sri Batchu currently leads Growth at Ramp. He previously led Growth Strategy and Operations at Instacart where he also helped grow their Ads business. Prior to that, he was one of the first 50 employees at Opendoor where he built, scaled, and managed a variety of business teams including Analytics, Sales, and Pricing.  During his time, the company grew from $100M to $5B+ revenue and to 1500+ people.  He started his career in management consulting at McKinsey and also held various investing roles including in private equity at Bain Capital. 

In Today's Episode with Sri Batchu We Discuss:

1. From Harvard to Private Equity to Leading the Best Growth Teams:

  • How did Sri make his way into the world of growth with Instacart and Opendoor?
  • What are 1-2 of his biggest takeaways from his time at Instacart? How did it change his approach and mindset towards growth?
  • How did Zilllow burn themselves by buying homes? What did that teach Sri about hitting metrics and goal setting in growth teams?

2. Growth Teams Should Fail and Fail Fast:

  • What is the right ratio of success to failure within growth teams?
  • What are specific ways that growth teams can increase the speed with which they fail?
  • How are the best post-mortems run? Who joins them? Who leads the agenda?
  • What are Sri's biggest lessons on how to set the right goals?
  • Where do so many growth teams go wrong with the North Star that they set for themselves?

3. Building the Bench: Hiring a Growth Team:

  • When is the right time to make your first growth hires?
  • What profile should your first growth hires be?
  • How should one structure the interview process when hiring growth teams?
  • What is the first question Sri asks all new hires?
  • Why does Sri believe you have to hire slowly?
  • Should candidates do case studies as part of the process, if so, on a new company or on the company they are interviewing for?

4. When Operators Become Investors:

  • Why does Sri believe the best investors of the next 10 years will be operators?
  • Why does Sri believe that operators can do due diligence to a higher level than traditional VCs?
  • Why does Sri believe that investors should not take cold emails?
  • Why does Sri believe that it is not wrong for an investor to hire from their portfolio companies?
  • What does Sri believe the future of venture holds over the next 10 years?

Jul 24, 2023

Adam Mosseri is the Head of Instagram, where he is responsible for overseeing the engineering, product, and business teams and leading Meta’s efforts on creators and Reels. Adam has been at Meta for more than fifteen years. He started at Meta as a designer for Facebook's mobile app before moving to product management, where he led the Facebook News Feed product and engineering teams, and served as the Head of Facebook News Feed. Adam began his career founding a design consultancy focused on graphic, interaction, and exhibition design before joining TokBox as the company’s first designer.

In Today's Discussion with Adam Mosseri We Discuss:

1. From Designer to Product Leader to Instagram CEO:

  • What did Adam learn from his first job bartending? How did it impact his approach to customer support and research?
  • What are the top 1-2 pieces of advice Adam would give to someone wanting to make the move from individual contributor to leader?
  • If Adam was "not amazing at anything", what did he do that enabled him to rise above the rest and become CEO of Instagram?
  • What have been 1-2 of the biggest lessons from working with Mark Zuckerberg for 15 years?

2. A Deep Dive on the Wild Times as Instagram CEO:

  • What has been Adam's single biggest mistake as CEO of Instagram?
  • What does Adam believe is the least known feature within Instagram that has made them successful?
  • What does Adam believe has been the biggest product decision he has made as CEO?
  • Why does Adam believe that Instagram is too complicated as a product?
  • Who does Adam believe is the most formidable competitor to Instagram?
  • Was Instagram Reels a simple copy of TikTok? What have Instagram learned from TikTok?
  • How does Adam respond to the statement that Instagram is a "copy-cat machine" and lacks innovaton?

3. Threads: The Journey from 0-100M Users in Three Days:

  • Did Adam and the team expect the response they got to Threads?
  • Why did they decide to break Threads out into a separate app?
  • What went into bootstrapping the Threads friendship and interest graph?
  • What was the Threads influencer activation strategy? What worked? What did not? Did they pay influencers? How did they choose which verticals to focus on?
  • What is Adam's core focus with Threads today?
  • How is the team analysing and measuring retention? What are their goals?
  • What are the 1-2 core reasons why Threads would not work? How do they aim to prevent them?
  • In 12 months, where will Threads be?

4. The Future of Consumer Social: What Happens Now?

  • Does Adam believe we have seen the transition from the social graph to the interest graph? Is it that binary?
  • Is it possible to have both the interest and the friendship graph all in one app?
  • How does the monetization potential differ when comparing Threads (text) to Instagram (visual)?
  • How important is it for the next consumer social platforms to have stars that are native to their platform (Mr Beast on Youtube, D'Amelio on TikTok etc.)

Jul 21, 2023

Jean-Denis Greze is Chief Technology Officer at Plaid where oversees global product business units across North America and Europe. Prior to joining Plaid, Jean-Denis was Director of Engineering at Dropbox. Jean-Denis is also a prolific angel investor with a portfolio including the likes of Nex Health, Merge.dev and Rupa Health to name a few.

In Today's Episode with Jean-Denis Greze We Discuss:

1. The Journey to One of the Most Powerful CTOs:

  • How JD made his way into the world of tech with his first role at Dropbox?
  • How does JD analyse a Linkedin CV today? What are the signals of outperformers?
  • What does JD know now that he wishes he had known when he started in tech?

2. Hiring the Best: 101:

  • What are JD's single biggest lessons on hiring the best talent?
  • What have been some of JD's biggest hiring mistakes?
  • Why does JD believe founders need to be as good at firing as they are hiring?
  • Does JD believe people can scale with the scaling of a company? If they do not scale, do you layer them or do you let them go?
  • How does JD determine whether to bring in an external candidate vs promote someone from within?

3. Product Differentiation is not Sustainable:

  • Why does JD believe that product differentiation is not sustainable? Why is UX as a moat BS?
  • How does this lead JD to suggest Salesforce is a short in the public markets?
  • Why does JD believe that Snowflake is also a short?
  • What does Snowflake teach us about the different stages of product market fit?
  • What are the biggest mistakes founders make when analyzing product market fit?

4. Remote Work, Titles and Entitlement:

  • Why does JD believe most tech employees treat their employer in the same way French citizens treat the French government?
  • How does JD analyse the impact of remote work on both productivity and culture?
  • Why does JD believe titles are BS in the beginning but matter with scale?
  • Why does JD believe that you should not hire for the long term?

Jul 19, 2023

Lauryn Isford is the Head of Product Growth at Notion, managing Notion's product-led growth engine and self-serve business. Before Notion, she led growth at Airtable, and previously worked on growth teams including Meta, Dropbox, and Blue Bottle Coffee. Lauryn is an active angel investor and advisor supporting companies building product-led go-to-market motions. 

In Today's Episode with Lauryn Isford:

1. From Blue Bottle to Airtable and Notion:

  • How did Lauryn first make her way into the world of product and growth?
  • What are 1-2 of her biggest takeaways from Dropbox, Facebook and Blue Bottle?
  • What does Lauryn know now that she wishes she had known when she started?

2. What is Growth: 101:

  • How does Lauryn define growth? What is it not?
  • When is the right time to make your first growth hire?
  • What profile should your first hire in growth be?
  • What are the single biggest mistakes founders make when hiring growth teams?

3. Mastering the Onboarding Experience:

  • What are the core elements of a successful onboarding experience?
  • How important is time to value in onboarding today?
  • What are the biggest mistakes product teams make in company onboarding?
  • What is the most effective onboarding technique and workflow in PLG today?
  • Why are 90% of current onboarding's done badly?

4. Making Growth work with the Rest of the Org:

  • What are the single biggest barriers to growth and product working together well?
  • What can leaders do to make their growth teams work well with product teams?
  • How can growth teams experiment and test with product without messing up codebases?

Jul 17, 2023

Dave Clark is the CEO of Flexport, the global freight forwarder and logistics platform that has now raised over $2.5BN to build the category leader. Prior to Flexport, Dave began his career at Amazon in 1999 as an Operations Manager, working his way up to become the CEO of Amazon’s worldwide consumer business in 2021. By the time Dave left, he was responsible for over 1 million employees. Dave spearheaded the launch of Amazon Robotics and grew the company’s logistics divisions to include Amazon’s own planes, trailers, and last-mile delivery vehicles through Amazon’s own delivery network (which today ships more packages than FedEx and UPS). Huge thanks to Ryan Peterson for some amazing question suggestions today.

In Today's Episode with Dave Clark We Discuss:

1. From Operations Manager to CEO @ Amazon:

  • How did Dave Clark make his way into the world of startups with Amazon in 1999?
  • What are 1-2 of his biggest lessons from spending 23 years at Amazon?
  • What are 1-2 of his biggest takeaways from working alongside Jeff Bezos for 23 years?

2. How Big Leaders Make Big Decisions:

  • What is Dave's decision-making framework when it comes to big decisions?
  • What is the biggest decision Dave made that went wrong? How did it impact his mindset?
  • How does Dave think through prioritisation as a leader today?
  • What are the biggest mistakes founders make when it comes to focus?

3. How Big Leaders Hire Big Talent:

  • What are 1-2 of Dave's biggest lessons on what it takes to acquire the best talent?
  • Does Dave believe that people can scale with the scaling of the company?
  • How does Dave think through the challenge of promoting internally vs bringing in external talent?
  • Why does Dave like to hire people straight out of college? What are the benefits?

4. How Big People Deal with Big Problems: Kids, Money and Ego

  • What are 1-2 of Dave's biggest lessons when it comes to parenting?
  • How does Dave think about giving his kids the same hunger and ambition, when they are brought up in such affluent environments?
  • How does Dave assess his own relationship to money? How has it changed over time?
  • What does a truly great marriage mean to Dave? Where do so many go wrong in trying to find work-life balance?

Jul 14, 2023

Sheel Mohnot is a Co-Founder and General Partner @ Better Tomorrow Ventures, a $225M fund that leads rounds in pre-seed and seed-stage fintech companies globally. Sheel and Jake (his co-founder) invested for many years together before founding BTV and wrote checks into Mercury, Flexport, Ramp, and Hippo Insurance to name a few. As for Sheel, before BTV he ran 500 Fintech for close to 7 years, and before that was a founder, founding two companies, both of which were acquired.

In Today's Episode with Sheel Mohnot We Discuss:

1. VC Needs to Change:

  • Why does Sheel believe that VCs should have smaller funds?
  • What are the biggest misalignments between founders and VCs today?
  • What are the biggest points of friction between VCs and their LPs today?

2. VC in 10 Years Time:

  • Who are going to be the winners in venture in 10 years time?
  • Who are going to be the losers?
  • Will micro-funds be bigger or smaller as a segment of the ecosystem?
  • Will solo-GPs be bigger or smaller? Were they a zero-interest rate phenomenon?

3. The Errors of a Bull Market:

  • What does Sheel believe are the single biggest mistakes made by VCs between 2020-2022?
  • Did Sheel take liquidity off the table in the last few years? What have been some of his biggest lessons on when to sell?
  • How does Sheel evaluate the flood of capital into emerging markets in the bull market? What happens now?
  • Fintech is also experiencing the same challenging time, how does Sheel assess what is happening in the fintech financing market today?

4. Building a Fund: Lessons, Mistakes and Advice Scaling to $225M:

  • What are the single biggest mistakes Sheel and Jake have made in the fun scaling? How has it impacted their mindset?
  • What does Sheel know now about fund management that he wishes he had known at the beginning?
  • What advice does Sheel give to emerging managers today, raising their first and second funds?

Jul 12, 2023

Kevin Egan is the Global Head of Enterprise Sales at Atlassian and brings more than 25 years of enterprise sales experience and leadership to the company. Prior to his current role, Kevin served as the Vice President of North America Sales at both Slack and Dropbox and has held various senior sales leadership positions at Salesforce.

In Todays Episode With Kevin Egan We Discuss:

1. The Makings of a Truly Great Enterprise Sales Leader:

  • How did Kevin first make his way into the world of enterprise sales?
  • What does Kevin know now that he wishes he had known when he entered sales?
  • What advice would Kevin give to a new sales leader today starting a new role?

2. The Sales Playbook:

  • How does Kevin define "the sales playbook"? Does the founder have to be the one to create the sales playbook
  • When is the right time to hire your first salespeople? Should they be senior or junior first?
  • What are the different types of reps to hire in the early days? Should you hire two at a time?

3. PLG vs Enterprise:

  • Does Kevin believe it is possible to run both PLG and enterprise playbook at the same time?
  • How does one know when they are ready to scale from PLG into enterprise? What are the signs?
  • What do companies need to change in the way their sales team, is structured to make the transition from PMG to enterprise sales?
  • What are the single biggest mistakes Kevin sees founders make in the scaling from PLG to enterprise?

4. Hiring the Sales Team:

  • What non-obvious characteristics and attitudes should we look for in sales reps?
  • How does Kevin structure the hiring process for all new additions to sales and revenue teams?
  • What makes good PLG sales leaders? How are they different from enterprise sales leaders?
  • What questions and case studies are most revealing for you in identifying them?
  • What have been some of Kevin's biggest lessons on comp structure for these early rep hires?

5. Making the Machine Work:

  • How does Kevin build trust with his early sales rep hires? What works? What does not?
  • How does Kevin balance hitting the quarterly revenue target with longer-term pipeline strategy?
  • How does Kevin manage when a quarter is missed? What is the right approach?
  • How does Kevin approach post-mortems and deal reviews? How often? What do the best entail?

 

Jul 10, 2023

Simon Sinek is an optimist and author, as we discuss in the show today. Simon is best known for his TED Talk on the concept of WHY (62M views), and his video on millennials in the workplace (80M views in 7 days). Simon is also a bestselling author including global bestseller Start with WHY, Leaders Eat Last and The Infinite Game. In addition, Simon is the founder of The Optimism Company, a leadership learning and development company, and he publishes other inspiring thinkers and doers through his publishing partnership with Penguin Random House called Optimism Press.

In Today's Discussion with Simon Sinek We Discuss:

1. The Makings of Simon Sinek:

  • In what ways does Simon believe that his parents and upbringing shaped who he is today?
  • What does Simon want to be when he grows up?
  • What was the catalytic moment to the "Simon Sinek brand"? When was that big break moment?

2. Identity:

  • Simon has said before, "I define myself by who I am and not what I do". Is it wrong to define yourself by what you do?
  • What do you do if you do not know who you are? What do you do if you do not like the answers to who you are?
  • Is it possible to change who you are? What does that process look like?
  • What is Simon's biggest advice to those looking to find a greater sense of self and identity?

3. Trust:

  • Does Simon start relationships with inherent trust and it is there to be lost or no trust and it is there to be gained over time?
  • When has someone broken Simon's trust? How did it impact how he approaches trust today?
  • In the case of cheating in a relationship, does Simon believe it is possible to regain trust over time?
  • Simon has said before, "trust is built on telling the truth". Does it ever make sense or is even right to tell a little white lie in a relationship?

4. Creating Safe Spaces:

  • How can we create safe spaces for our partners to be their full selves?
  • Does this differ professionally and personally?
  • What are the biggest mistakes people make in building safe spaces?

5. Listening:

  • What does great listening in a relationship mean? How can we do it better?
  • Often people jump from listening to solution mode, is that wrong?
  • Why does Simon have a rule of “no crying alone”. What does it do and how is it productive? When was the last time Simon cried?

6. Simon Sinek: AMA:

  • What is success to you?
  • Can one be “successful” and unhappy?
  • What is the difference between happiness and joy?

Jun 30, 2023

Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses. Last month Contextual closed a $20M funding round including Bain Capital, Sarah Guo, Elad Gil and 20VC. He is also an Adjunct Professor in Symbolic Systems at Stanford University. Previously, he was the Head of Research at Hugging Face, and before that a Research Scientist at Facebook AI Research.

In Today's Episode with Douwe Kiela We Discuss:

1. Founding a Foundational Model Company in 2023:

  • How did Douwe make his way into the world of AI and ML over a decade ago?
  • What are some of his biggest lessons from his time working with Yann LeCun and Meta?
  • How does Douwe's background in philosophy help him in AI today?

2. Foundational Model Providers: Challenges and Alternatives:

  • What are the biggest problems with the existing foundational data models?
  • Will there be one to rule them all? How does the landscape play out?
  • Why does Douwe believe OpenAI's data acquisition strategy has been the best?

3. Data Models: Size and Structure:

  • Why does Douwe believe it is naive to think the open approach will beat the closed approach?
  • What are the biggest downsides to the open approach?
  • Does the size of data model matter today? What matters more?
  • How important is access to proprietary data? Are VCs naive to turn down founders due to a lack of access to proprietary data?

4. Regulation and the World Around Us:

  • How does Douwe expect the regulatory landscape to play out around AI?
  • Why is Europe the worst when it comes to regulation? Will this be different this time?
  • How does Douwe analyse Elon's petition to pause the development of AI for 6 months?
  • Do founders building AI companies have to be in the valley?

Jun 28, 2023

Jennifer Hyman is the Co-Founder and CEO of Rent the Runway, the world’s first and largest shared designer closet. Under Jennifer’s leadership, RTR has made history by being the first company to go public with a female founder/CEO, COO, and CFO. Jennifer serves on the Board of The Estée Lauder Companies and Zalando, and also is a Founding Member of the NYSE Board Advisory Council, a Member of the Women.nyc Advisory Board and a Member of the Launch with GS Advisory Council for Goldman Sachs.

In Today's Episode with Jennifer Hyman We Discuss:

1. The 14-Year Overnight Success: Scaling Rent The Runway To IPO:

  • What was the a-ha founding moment for Jennifer with RTR?
  • What does Jenn know now that she wishes she had known at the beginning?
  • Does Jenn believe that naivete is good or not when starting a business?

2. Building the Best Team:

  • What have been Jenn's single biggest lessons when it comes to acquiring the best talent?
  • What have been Jenn's biggest hiring mistakes over the years?
  • How does Jenn approach the interview process? Why does Jenn not focus on their professional career and achievements? What questions does she ask?
  • What does Jenn believe are the single biggest mistakes founders make when building their teams?

3. Building the Business for IPO and Beyond:

  • Why does Jenn wish she had run RTR as a private company in the same way she does now as a public company? How does the way you run the company differ?
  • What about the unit economics of RTR suggesting it is a fundamentally better business than apparel competitors? How have their margin profiles changed over time?
  • Why does Wall St not love RTR? What is required for that to change? Why does Jenn believe the street is wrong on how they analyse RTR?

4. Boards 101: Leading and Learning from Estee Lauder:

  • What are Jenn's biggest lessons to founders on how to manage boards successfully?
  • What have been 1-2 of Jenn's biggest lessons from being on the Estee Lauder board?
  • What do the best board members do? What do the worst board members do?

Jun 26, 2023

Akin Babayigit is a serial entrepreneur and an active angel investor. He is currently the Founder and COO of Tripledot Studios, one of the fastest-growing mobile gaming companies in the world, which was recently valued at over $1.4BN. In just 4 years, Tripledot grew to generate several hundred million dollars per year in revenue and currently entertains over 50 million people every month. Tripledot was recently named as the #1 fastest-growing European company by FT, as well as being named as the fastest-growing Tech business in the UK, in the annual “UK Tech Awards”.

In Today's Episode with Akin Babayigit We Discuss:

Entry into the World of Startups and Gaming:

  • How Akin made his way from Turkey to HBS and founding a unicorn in Tripledot?
  • How did the lack of a father figure impact Akin's approach to parenting?
  • What are 1-2 of Akin's biggest takeaways from his time at Facebook, Skype and King.com?
  • What advice would Akin give to all new joiners at a company today?

90% of Startup Advice is Total BS:

  1. BS Myth #1: "You have to be passionate about your domain". Why does Akin disagree with this? If you do not have passion for the domain, what do you have to have?
  2. BS Myth #2: "You have to be solving a real problem". Why does Akin disagree with this mantra? If you are not solving a real problem, what should you be solving?
  3. BS Myth #3: "When you do a startup, your life will suck for a long period of time". Why does Akin strongly disagree with this? Does it get easier over time? What does Akin advise founders to make the earlier days easier?
  4. BS Myth #4: "Focus is everything. You should focus on a single thing and only do that." Why does Akin believe that focus can be dangerous? How should founders know when to pivot vs when to keep going?
  5. BS Myth #5: "Mission and vision statements are so important." Why does Akin believe that the majority of mission statements are BS? Is it worth having them at all?
  6. BS Myth #6: "You should hire people with domain experience." Why does Akin believe you should hire people who do not have domain experience? What does Akin look for in these candidates? What have been his biggest hiring mistakes? How has his hiring changed over time?
  7. BS Myth #7: "Speed is the most important thing." Why does Akin believe that speed can be dangerous? When is it right to go fast vs go slow?
  8. BS Myth #8: "Valuations matter and you should optimize." Why does Akin believe that valuations do not matter in the long run? How should founders approach the valuation discussion with this in mind?

Jun 23, 2023

Rob Go is a co-founder and Partner at NextView, one of the leading seed firms of the last decade with a portfolio including Attentive, Devoted Health, Whoop, and Grove Collaborative. Prior to co-founding NextView, Rob was an investor at Spark Capital and held product and product marketing roles at Ebay. He began his career as a consultant at The Parthenon Group.

In Today's Episode with Rob Go We Discuss:

1. Entry into the World of Venture:

  • How a cold call from a VC firm led to Rob entering the world of venture?
  • Why does Rob believe venture is a young person's game?
  • What does Rob know now that he wishes he had known when started in venture?

2. Preparing Docs for a Fundraise:

  • What docs should fund managers have ready before they start the raise?
  • How should they structure their data room?
  • Where do the majority of LPs spend their time, document-wise?
  • What are the single biggest mistakes emerging managers make preparing docs for a raise?

3. Meeting Your First LPs:

  • What is the best way for emerging managers to meet LPs for the first time?
  • Should they send the deck before or after the meeting?
  • What questions should emerging managers ask to qualify LPs in or out of a meeting?
  • What are some clear early signs that a first meeting went well?

4. Closing LPs: The Tips and Tricks:

  • How important is it for a fund to have an anchor?
  • How much of a fund should the anchor be?
  • Are there different qualities of anchor LPs?
  • Should managers ever sell part of their GP or give an LP part of the carry?
  • What can managers do to enforce a sense of urgency to get LPs over the line?
  • What are signs that an LP will not invest in the fund without rejecting you yet?
  • Should emerging managers impose a minimum check size on new LPs?

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