David Tisch is the Managing Partner of BoxGroup, one of the leading seed-stage investment firms of the last decade having invested in over 500 seed-stage startups, including Plaid, Ro, Ramp, PillPack, Amplitude, Stripe, Warby Parker, Harry’s, Flexport, Classpass, Airtable and more.

Terrence Rohan is the Managing Director @ Otherwise Fund, a fund that discretely empowers a network of today's top founders to make multi-stage venture investments. Terrence has invested in the likes of Figma, Hugging Face, Vanta, Notion and Robinhood to name a few.

In Today's Seed Investing Special We Discuss:

1. Is Seed Investing Now a Commoditised Asset Class:

• Why does Dave Tisch believe seed investing will remain the most inefficient market? What does that mean for the future of returns at seed?
• Why should you always pay up and be price-insensitive at seed rounds?
• Why does David believe that no one is great at seed investing?
• Why does David believe that you cannot index the seed market?

2. The Biggest BS Elements of Venture Capital:

• Signaling: Why does David believe that the theory of signaling is total BS? Why does Terrence disagree and think it is valid and common?
• Group Decision-Making: Why does Terrence believe that investing decisions should be made solo and groups merely encourage consensus decision-making?
• Reserves: Why does Terrence believe reserves hurt DPI and are not good? How does David respond given his growth fund?
• Venture Value Add: Why do David and Terrence think venture value add services platforms are BS and not worth it?

3. The World of LPs:

• What is the single biggest misalignment between VCs and LPs?
• What are David and Terrence's biggest pieces of advice for emerging managers today?
• Should LPs expect depressed returns from venture as the asset class commoditises?

Will Wu is the CTO @ Match Group, the owner and operator of the largest global portfolio of popular online dating services including Tinder, Match.com, OkCupid, and Hinge to name a few. Prior to Match, Will was VP of Product at Snap Inc. As the 35th employee, Will spearheaded the creation of Snapchat’s “Discover” content platform. He also led the creation and growth of the “Chat” messaging feature, which today is a primary Snapchat engagement driver that connects hundreds of millions of people each day.

In Today's Episode with Will Wu We Discuss:

1. The Journey to Snap CPO:

• How did Evan make his way into the world of product and come to meet Evan Spiegel?
• What are 1-2 of his biggest takeaways from his time at Snap?
• What does Will know now that he wishes he had known when he started in product?

2. How to Hire Product Teams:

• How does Will structure the interview process for new product hires?
• What are the most telling questions of a candidate's product skills in hiring?
• What case studies and tests does Will do to assess a candidate?
• What are 1-2 of Will's biggest hiring mistakes in product?

3. How to Do Product Reviews Effectively:

• What are Will's biggest lessons on what it takes to do product reviews well?
• What are the biggest mistakes product leaders make in product reviews?
• How can teams drive focus in product reviews? What works? What does not?

4. Product: Art or Science?

• How does Will balance between gut/intuition and data in product decisions?
• Is simple always better in product design?
• What is human-centered design? How does it impact how Will approaches product?

Dave Kellogg is one of the OGs of Saas. Among his many accomplishments, Dave was the CMO of Business Objects where he helped scale the business from $30M to $1BN in revenue. Dave has also been a CEO twice, once scaling the business from $0 to $80M and the other business from $8M to $50M before selling it. Dave is also an advisor to some of the best including GainSight, Logickull, MongoDB, Pigment, Recorded Future, and Tableau.

In Today's Episode with Dave Kellogg We Discuss:

1. What are the Metrics That Matter:

• Why is CAC payback period such a flawed metric?
• What is CAC ratio? Why is it more effective than understanding payback?
• Why is gross revenue retention more important than net revenue retention?
• What are the single biggest mistakes that founders make when using metrics today?

2. How to Build and Scale the Best Sales Teams:

• Why should founders hire three sales reps at one time? What is the benefit?
• What are the three different types of sales calls all teams must have?
• What should all CEOs and Heads of Sales ask of their sales team in forecasting?
• What is the single biggest mistake most companies make in forecasting?
• How should a CEO/board member respond to a sales team that lets a deal slip to next quarter?

3. Are CFOs Buying New Tech and How to Win Renewals:

• Are CFOs open for business? How has the top down sales process changed in the last year?
• Why is the way that startups think about renewals completely broken?
• What are the three different types of customer success teams we have today?
• What is the core role of customer success? How can we incentivise them to sell more?

4. Mastering Product Marketing, Customer Profiles and Crossing the Chasm:

• How can we use product marketing to increase sales velocity?
• What is the single biggest risk in product marketing today?
• What does Dave mean when he says "an ICP starts as an aspiration and becomes a regression?"

Ryan Akkina is a member of the Global Investment Team at the MIT Investment Management Company (MITIMCo), which is responsible for managing MIT's endowment and pension plans. Ryan has invested in the likes of Sequoia, Kleiner Perkins, a16z, Greenoaks and Initialized to name a few. Ryan also leads many of MITIMCo's direct co-investments including most notably into Coupang and Rippling. Prior to joining MITIMCo, Ryan was a consultant at McKinsey & Company.

In Today's Episode with Ryan Akkina We Discuss:

1. From Engineer to LP with MIT:

• How did Ryan make his way into the world of fund investing as an LP with MIT?
• Why did he turn down the chance to be a VC early in his career?
• What does Ryan know now that he wishes he had known when he started at MIT?

2. The Manager Evaluation Process for MIT:

• What does Ryan look for most when investing in new managers?
• How important is track record when evaluating a new manager?
• What is the biggest mistake Ryan has made in picking a manager? What did he not see that he wish he had seen? How did that change his process?

3. How MIT Builds Their Portfolio:

• How does MIT construct their portfolio from private to public to everything in between?
• What are the three different types of check sizes that MIT writes when investing in new managers?
• What are the most common reasons why MIT will not re-up with a manager?
• What are the single biggest reasons why great managers turn bad?

4. MIT: The Direct Investor:

• Why does MIT see so much opportunity in direct investing?
• How does MIT approach the direct investing process? How do they approach underwriting themselves vs working with their managers in the process?
• How do MIT think about the right number of direct deals to make up their portfolio?
• How do they approach check sizing on a per-company direct investment?
• What has been Ryan's biggest direct investing mistake? How did that change his approach and mindset?

5. LP Markets Today and Where We Go From Here:

• Are LPs open for business today? What type of firms will not struggle? Which will?
• How does Ryan view liquidity windows today? When will M&A and IPO markets open?
• What would Ryan most like to change about the world of LPs?
• Why does Ryan believe the LP incentive structure in terms of compensation is broken?

Dave Ripley is the CEO @ Kraken, one of the world's largest cryptocurrency exchanges, valued in 2022 at a whopping $10.8BN. Prior to Kraken, Dave was the Co-Founder of Glidera, a market-leading Blockchain technology company that Kraken acquired in 2016.

In Today's Episode with Dave Ripley:

1. From Boston Consulting Group to CEO of Kraken:

• How did Dave first make his way into the world of crypto?
• What are the single hardest elements of a CEO transition?
• What does Dave know now that he wishes he had known about CEOship?

2. What is the Usage for Crypto:

• Other than as a store of value, what application usage does crypto serve?
• Global payments are fine as is and are improving, why do they need crypto?
• Global remittance is served by Remote and Deel, why do they need crypto?
• No applications have been provided well, what really is the use case that makes sense?

3. Should Gensler Be Let Go and The SEC is Wrong:

• Why is the approach of the SEC completely flawed?
• Should Gensler be fired for his ineffectiveness?
• What is the right policy stance and approach to take from here?

Sean Murray is the CRO @ Greenhouse which is the fourth company Sean has scaled successfully into the enterprise. Sean's prior roles include revenue leadership positions at Saleloft (CRO), Xactly (VP Sales), and CEB, now Gartner (Head of MID Global Sales).

In Today's Episode with Sean Murray

1. The Origin Story: Is a Love of Sales Born:

• How did Sean first fall in love with Sales?
• What does Sean know now that he wishes he had known when he started his career in sales?
• What is Sean's biggest advice to a young person entering the sales world today?

2. Sales has Changed; You Need to Change with It:

• Why do CMOs need to be good sellers and CROs need to be good marketers today?
• Have we seen the total blending of sales and marketing today?
• Should we get rid of all sales teams and just have content marketing teams?

3. How to Move into the Enterprise Successfully:

• What are the three biggest mistakes startups make when scaling into the enterprise?
• What easy wins can they do early in the sales process to enterprises to get a good start?
• How important are logos? Does social validity really work in enterprise?
• How should sales teams use discounting in enterprise sales most effectively?
• What is the right way for sales leaders and CROs to budget for enterprise?
• Is there a way to test enterprise without committing the company and a lot of resources?

4. How to Build the Best Sales Team Today:

• What is the right hiring process for all new sales hires?
• What are the questions you have to ask in the interviews?
• What do the case studies entail? What are signals of the best reps?
• What are the biggest mistakes teams make when hiring new sales reps?
• What have been Sean's biggest lessons on comp and negotiation with new reps?

Adam Fisher is a Partner @ Bessemer Venture Partners and one of the most successful investors in Israel over the last two decades with seed investments in Fiverr, Wix, Melio, HiBob and more. Adam has now made over 60 investments and has had an incredible 23 successful exits. Adam has now been in venture for over 27 years having started his career at Jerusalem Venture Partners in 1996.

In Today's Episode with Adam Fisher We Discuss:

1. Lessons from 27 Years in Venture Capital:

• How did Adam first make his way into the world of venture straight out of college?
• Does Adam agree with Doug Leone that VC has changed from a "boutique, high margin business to a commoditized, low margin industry"?
• What does Adam know now that he wishes he had known when he started in venture?

2. How to Pick Winners: 23 Exits in 60 Investments:

• To what extent does Adam think pattern recognition is a good thing? When is it bad?
• Does Adam prefer to invest in outsider founders approaching a problem with fresh eyes or insider founders who know the problem back to front?
• Why does Adam believe that "category creation is BS"?
• Why does Adam not like to invest in big, hugely ambitious markets? Why are smaller markets best?

3. The Deal: Mastering the Art of Negotiation and the Deal:

• How does Adam reflect on his own relationship to price?
• When doing an investment, does Adam think about who would do the next round?
• How important is ownership to Adam? Does he want it all on first check?
• Why does Adam not like to invest in hot AI rounds?
• What have been Adam's single biggest investing mistakes? How did it change his approach?

4. Mastering the Art of Portfolio Management:

• Why does Adam believe that it is impossible to know which of your portfolio will be the breakout winners early on?
• How does Adam approach reserve allocations with this in mind?
• How does Adam know when is the right time to sell a position?
• What does Adam believe was the biggest sin of the zero interest rate environment period?

Zaria Parvez is Duolingo’s Senior Global Social Media Manager where she is famed for scaling Duolingo's TikTok from 50K followers in September 2021 to 8M followers today. The Duolingo TikTok has 143 viral videos (view counts of 1M or higher) due to Zaria’s creativity. What started as a test-and-learn initiative has become Duolingo's most successful social buzz and word-of-mouth initiative to date – all because of Zaria's insights, instincts, and expertise.

In Today's Episode with Zaria Parvez:

1. From College Student to TikTok Star:

• How did Zaria make her way into the world of social media and Duolingo?
• When did Zaria realize the power of TikTok? What did she do as a first step?
• What does Zaria know now about growing on TikTok that she wishes she'd known when she started?

2. How to Create a Viral Video:

• What have been Zaria's biggest lessons in what it takes to create a viral video?
• What does Zaria mean when she says the best content is "medicine to candy"?
• What does the ideation process look like for new content ideas?
• How much budget should be set aside for new content?
• What does Zaria mean when she says Duolingo's TikTok needs to view like a "sitcom"?

3. How to Tie Success in Content Back to Hard Dollars:

• How is "success" in content measured at Duolingo?
• How fast does Zaria know if a video is a hit or not? What is the right cadence to post?
• How should companies determine whether content is ultimately successful or not?
• What is the single metric that Zaria is focused on today?

4. How to Build the Best Content Team:

• Why should companies not work with content agencies if they want the best results?
• Why does Zaria believe you have to hire troublemakers if you want success in content?
• What are the single biggest mistakes companies make w

Shyam Sankar is Chief Technology Officer and Executive Vice President of Palantir Technologies in addition to the Chairman of Ginkgo Bioworks. Shyam holds a B.S. in Electrical and Computer Engineering from Cornell University and a M.S. in Management Science and Engineering from Stanford University.

In Today's Episode with Shyam Sankar:

1. Journey to the Top of Defence:

• How did Shyam make his way into the world of startups and get a role with Kevin Hartz at Xoom?
• How did seeing Shyam's parents lose everything impact his mindset and drive?
• What does Shyam know now that he wishes he had known when he started his career?

2. How the World's Governments Buy Defence:

• What is the playbook for selling defence to different governments?
• Why is the way that governments purchase and procure so broken?
• If Shyam were head of the DOD, what would he change?
• Why does the DOD "need to pick winners"?
• Which governments are the best to work with? Which are the worst?

3. A World In Conflict: What Changes:

• How does conflict change the buying process and urgency for governments?
• How do elections change the buying cadence and process for different governments?
• Looking forward to 2024, how does Shyam predict the state of different global conflicts?

4. Hiring 101: You Have To Hire Artists:

• What have been Shyam's single biggest lessons on what it takes to hire the best of the best?
• Why does Shyam believe that hiring great people is like talent management in Hollywood?
• Why does Shyam believe talent should be "shielded from budgets"?
• What have been some of Shyam's biggest hiring mistakes? How did he learn from them?

Brian Halligan is the Co-Founder and Executive Chairperson of HubSpot. Brian led the business as CEO for 15 years from Day 1 to a $30BN public company with 7,000 employees. Among Brian numerous achievements, Brian is famed for coining the term "inbound marketing", he is a globally recognised author, he is also an incredible teacher having developed MIT’s popular Scaling Entrepreneurial Ventures class. In addition to all of this, he is also the Co-Founder of Propeller Ventures, a $100 million climate tech venture fund, specializing in ocean innovation investments.

In Today's Episode with Brian Halligan We Discuss:

1. The Makings of a Generational Defining Entrepreneur:

• How did the first job as a paperboy lead to the founding of a $30BN company?
• How does Brian analyse the importance of luck vs skill in success?
• What is Brian running from? What is he running towards?

2. How to Be the Best Leader from 15 Years as CEO:

• What are Brian's biggest lessons in leadership from Elon Musk and Jensen Huang?
• How has Brian's leadership style changed over time?
• Why is the way leaders prioritise what they do today completely broken?
• How can leaders use quarterly goals to prioritise most effectively?
• Does Brian believe people are born CEOs? Are MBAs worth it for CEOs?

3. How to Build the Best Team:

• What is the #1 failure condition of teams today?
• Why does Brian believe most of your employees are mercenaries and not missionaries? Is that ok?
• Why do recovery plans never work? Once lost, can trust in teams be regained?
• Are people destined for certain stages of company growth?
• Why does culture always break when teams hit 100 people?

4. The Best Deal in VC History:

• Why did Hubspot sell 47% of the company to General Catalyst in their Series A?
• How did Sequoia come to lead their Series D?
• How much of a needle mover is it for companies and founders to have Sequoia invest?
• Why did Brian sell secondary to Sequoia in the Series D? Is it the most costly mistake he has made?

Keith Rabois is a Managing Director @ Khosla Ventures and one of the most respected venture investors of the last decade. Keith has led investments in Stripe, Faire, Ramp, Affirm and many more. Just last week, Keith announced he would be rejoining Khosla from Founders Fund, where he spent an immensely successful 5 years as a General Partner. Prior to Founders Fund, Keith started his career at Khosla where he spent 6 years and led investments in DoorDash, Opendoor, Webflow and more.

In Today's Episode with Keith Rabois We Discuss:

1. The Decision to Rejoin Khosla Ventures:

• Why did Keith decide to rejoin Khosla Ventures from Founders Fund?
• What did Keith miss most that Khosla did, that Founders Fund did not?
• How did Delian take the news?

2. Comparing Two Great Firms: Founders Fund vs Khosla Ventures:

• Investing Style: How does Keith compare the investing styles when analyzing FF and KV?
• Price Discipline: Which firm is more price-disciplined? Does price discipline even matter?
• What are the single biggest mistakes Keith has made on price? How did it change how he invests?
• Founder Type: What sort of founder would choose KV? What founder would choose FF?
• How did the depth & quality of investment decision-making compare between KV and FF?

3. What It Takes To Win in Venture in 2024:

• Liquidity: What have been Keith's biggest lessons on when is the right time to sell positions?
• Capital Planning: What have been Keith's biggest lessons on the most effective use of reserves?
• Why does Keith believe if you do not lose some deals as an investor, you are not competing for the right companies?
• Khosla Ventures recently raised $3BN. How important is the ability to support companies across their lifetime in 2024 vs stage specific?

4. Where is The Best Place to Invest:

• Why does Keith think seed is the best place to be investing today?
• Why despite the better risk/reward profile, does Keith think Series A is not the best place to invest?
• Does Keith believe we will see the return of growth investing in 2024?
• What does Keith predict for the M&A market in 2024? Did Figma kill all activity?
• When will the IPO windows open again? Why would Stripe go out this year?

5. Keith Rabois: AMA:

• Why did Keith not want to start his own fund? Will he ever?
• What have been Keith's biggest lessons from working with Vinod Khosla and Peter Thiel?
• What were Keith's biggest lessons from Roelof Botha on what it takes to be an effective board member?
• How does Keith think about bitcoin in 2024?

Jamin Ball is a Partner @ Altimeter Capital where he sits on the board of Airbyte, Clickhouse, dbt Labs, Prisma, Tabular. Jamin has also led investments in Deel, MotherDuck, Personio and Starburst. Prior to Altimeter, Jamin spent 5 years at Redpoint where he led investments in Workato, Monte Carlo, Cityblock Health, Root Insurance.

Ed Sim is one of the best seed round investors in venture as the Founder and Managing Partner @ Boldstart, Ed focuses specifically on developer, infra and SaaS at pre-seed and seed round. Over the last decade, Ed has backed some of the best including Snyk, BigID, Kustomer, Front and Superhuman.

In Today's Episode We Discuss:

1. How to Invest Successfully in 2024:

• What are the three biggest mistakes growth investors can make in 2024?
• Why should founders not start a platform company?
• What were Jamin and Ed's biggest mistakes from the ZIRP era?
• How does Jamin justify paying an $8BN price for Hopin? What were his lessons?

2. The M&A Markets in 2024:

• Did Figma kill the M&A markets for 2024? What should we expect in M&A?
• Why will private companies buying private companies be a massive segment in 2024?
• What are Ed and Jamin's biggest tips to founders considering selling their company in 2024?

3. When Will IPOs Come Back:

• What will be the catalyst to the opening of the IPO markets?
• Will Stripe and Databricks go public in 2024? What others should we expect?
• What are the three requirements for a company to go public in 2024?

4. Firesales: Investors Need Cashback:

• Why does Ed believe now is the time in the cycle where late-stage investors want cash back to distribute back to their LPs or to recycle?
• What should we expect to see in terms of acqui-hires and firesales?
• What are the different incentives when comparing founders vs early stage VCs vs late stage VCs when it comes to acquisitions?

Nick Tomaino is the Founder and General Partner @ 1confirmation, one of the leading seed firms fueling the decentralization of the web and society. The fund started with $26M and the firm now has over $1B in assets under management. Nick is famed for being one of the first investors in OpenSea.

Kyle Samani is the Co-Founder and Managing Partner @ Multicoin Capital, one of the leading crypto native funds of the last decade with positions in Solana, FTX, Fractal, and Helium to name a few.

In Today's Episode We Discuss:

1. Moving Away from a Shitcoin Casino:

• What will it take for crypto to move away from being shitcoin casino?
• Why does Nick believe that "crypto has been a free for all and greed got the better of people"?
• Why does Nick believe that crypto shilling will reduce the amount of violence in the world?

2. FTX: The Biggest Ponzi Scheme in Plain sight:

• How does Kyle reflect on SBF and FTX today? Should he have known it was a fraud?
• How did Nick see so far ahead of time that SBF was not genuine?
• What are the most striking lessons when comparing Coinbase's Superbowl advert to FTX's?

3. Where Politics and Crypto Collide:

• SBF was one of the largest donors to Biden, what does this say about the rise of "crony capitalism"?
• What candidates running in the election will be best for crypto?
• Why will Trump win the election and be the first President to rule from a prison cell?
• Why is the strategy pursued by Gensler and the SEC so flawed?

4. The Great NFT Comeback, The Crypto IPO Season:

• What will be the next crypto company to IPO? When?
• When will NFTs come back? What will cause this?
• Will Opensea ever be worth $13BN again? What is their future?

Joining Harry in the hot seat today is Jason Lemkin, Founder @ SaaStr and one of the OG SaaS investors of the last decade. The discussion today is broken into two segments:

2023: A Year in Review:

• Breakout company
• Best early-stage fund
• Best late-stage fund
• Most surprising event
• Founder of the Year

2024: Predictions: What is to Come:

• Does the IPO window open?
• Do Stripe, Databricks, and more go public?
• What happens to early-stage venture markets?
• Does the growth stage come roaring back?
• What happens to the M&A market?
• How does Trump change the startup ecosystem?
• Will a generation of young VCs be washed out the system?
• Will a ton of venture firms shut down?

Dave Powers serves as President and CEO of Deckers Brands, a global footwear and apparel company where he focuses on the company’s five high-performing brands: UGG®, Teva®, Sanuk®, HOKA One One® and Koolaburra®. Prior to Deckers, he held executive leadership roles at Converse and Timberland, where he led worldwide retail merchandising, marketing, visual and store design as well as the creation of a sustainable line of footwear and apparel.

In Today's Episode with Dave Powers:

1. The Unlikely CEO of a Global Footwear Company:

• How did Dave make his way into the world of consumer and fashion from the ground up?
• Why did Dave never think he was the type of person to be a CEO?
• What does Dave know now that he wishes he had known when he started his career?

2. From $1.1M Acquisition to $1.4BN Revenues: The Hoka Story:

• Why did Deckers acquire Hoka for $1.1M? What did they see in this, at the time, futuristic running shoe that no one else saw?
• Was the growth of Hoka linear or were there needle-moving moments that propelled the brand?
• What did they do so right that led to their success?
• What would Dave have done differently in the Hoka journey if he had his time again?

3. From $14.7BN Acquisition to Oprah's Favourite: The UGG Journey:

• How much of a needle mover was it for UGG when Oprah added it to her list of favourite items?
• Why did UGG go through a tough period? What did they do wrong?
• What does it take to resurrect a brand? How can they bring UGG back to life and make it cool?

4. From Abercrombie to LVMH: An Analysis of the Industry:

• How does Dave analyse the rise and fall of Abercrombie and Hollister? Where did it go wrong?
• What does Dave believe LVMH are the best in the world at? What does he learn from them?
• How important is it for consumer companies to have a hero product?
• How can consumer companies scale to mass markets without losing their core audience?

Gustav Söderström is the Co-President, CPO & CTO at Spotify. Gustav has been instrumental in taking Spotify from a 30-person operation in Sweden when he joined to being the global leader of the space.

Scott Belsky is Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. 

Tomer Cohen is the Chief Product Officer @ Linkedin where he is responsible for setting and executing the global product strategy at LinkedIn.

In Today's Episode on How AI Changes The Future of Product and Design We Discuss:

1. Why AI Is Now the Product that UI Serves:

• Why does Gustav believe that AI is now the product?
• How has the importance of UI changed with the rise of AI?
• How did TikTok change the product paradigm over the last few years?

2. What Matters More Models or Data:

• What is more important the size of the model or the amount of data a company has?
• Will companies use many models at the same time?
• Why will companies using many models at once create a huge opportunity for startups?
• Will every company have their own model? What will be the decision-making framework of whether to have your own model or leverage another?
• How does the rise of AI change how companies approach data acquisition, collection and cleaning?

3. The Workforce Needs to Change with AI:

• How do product leaders and teams need to change in an AI-first world?
• What do designers need to do to stay up to date in an AI-first world?
• What does it mean to be good at prompting? How can people get good at prompting?
• Why will AI kill companies that charge by the hour?
• Why will seat pricing die in a world of AI? What will be the business model for AI?

4. Incumbents vs Startups: Who Wins:

• Do incumbents win in a world of AI or do startups?
• Why is AI primed for incumbents to win and move fast in a way they could not in prior technology cycles?
• What are the biggest hurdles and challenges incumbents have to face that startups do not?
• What are the biggest barriers that startups have to win in a world of AI that incumbents do not have?

Peter Lacaillade is a Managing Director @ SCS Financial Services where he leads its private investment program where he oversees the firm’s activities in private equity, opportunistic credit and private real assets. Peter has been an early backer of Thrive, Founders Fund, a16z, Greenoaks and 20VC. Before SCS, Peter was an Associate at HarbourVest Partners in its Secondary Group where he analyzed venture capital, growth equity and buyout investments.

In Today's Episode with Peter Lacaillade We Discuss:

1. Becoming One of the Great LPs in Venture:

• How did Peter make his way into the world of fund investing as an LP?
• What does Peter know now that he wishes he had known when he started as an LP?
• Why does Peter believe now is the best time to be investing in newer, emerging managers?

2. How to Pick the Best Venture Managers:

• What are the commonalities in the best VCs Peter has invested in?
• How important is track record for Peter when evaluating managers?
• What mistakes has Peter made when it comes to manager selection? What did he learn?
• How do the best managers build relationships with their LPs?

3. Building a Portfolio That Can 5x:

• In a venture fund portfolio, what is the distribution between those that outperform, perform as planned and then underperform?
• How does Peter invest in both large franchises and emerging managers with a barbell approach? How much in established franchises and how much in emerging managers?
• Are managers actively marking down their portfolios in the last 18 months? Who has been the best at this and who has been the worst? How much should portfolios be marked down?
• How does Peter evaluate the compression of deployment timelines we saw in the last 18 months?

4. A Breakdown of the LP Landscape:

• Family Offices: What are the biggest dangers of having family offices as LPs? Why do multi-family offices tend to be better?
• Endowments: Are they really as stable as people think they are? What separates a good vs great endowment? Who stands out?
• Fund of Funds: Why does Peter think fund of funds deserve more credit? How should managers think about working with FoFs most effectively?
• What is the right level of concentration managers should have between these different LP profiles?
• What are the biggest mistakes emerging managers make when approaching LPs?

Davis Smith is the Founder and Chairman of Cotopaxi, an outdoor brand with a humanitarian mission. The company has assisted over 4 million people living in poverty. The company has been profitable for the last 4 years and is expected to do $160M in revenue in 2023, up from $55M just two years before. In April 2023, Davis resigned after 10 years as CEO to lead a mission for his church in Brazil for three years. Davis is an EY Entrepreneur of the Year and was recognized as Utah’s Businessperson of the Year in 2022. He is an adventurer who has floated the Amazon on a self-made raft, kayaked from Cuba to Florida, and explored North Korea.

In Today's Episode with Davis Smith We Discuss:

1. From Selling $6M Worth of Pool Tables to the Amazon of Brazil to Founding Cotopaxi:

• How did Davis scale a pool table business to $6M in revenue?
• What were Davis' biggest takeaways from building the Amazon of Brazil, raising millions in VC funding and the business failing?
• How did depression and 36 hours on a sofa lead to the a-ha moment for Cotopaxi?

2. The Billion Dollar Company, Rejected by 100 Investors:

• How was the early fundraising journey for Davis with Cotopaxi? Why did so many investors say no?
• What was the best VC meeting he has ever had? Why do women understand Cotopaxi better?
• What does Davis believe are the biggest misalignments between VCs and Founders?
• Why does Davis believe we need a new type of financial product to fund long term projects?
• What are the biggest elements of fundraising that Davis believes founders do not understand?

3. Scaling Cotopaxi to $150M in Revenue:

• What are Davis' biggest lessons on what works and what does not from scaling Cotopaxi to $150M in revenue?
• Why did Davis not lay anyone off but decide everyone should take a pay cut instead? How did that go down?
• Why does letting people leave work earlier lead to better talent wanting to join your company?
• Why does Davis believe that you absolutely can build a huge business with balance in your life?

4. Life, Parenting, Marriage:

• Why does Davis believe that so many entrepreneurs chase the wrong thing? What do they chase? What should they be chasing instead?
• How does Davis analyze his relationship to money today? Does it make you happy?
• What does great parenting mean to Davis? How has that changed over time?
• How does marriage change when comparing pre-kids and post-kids?
• Was Davis nervous about becoming a father for the first time at the age of 24?

Steve Goldberg is the Chief Revenue Officer at Salesloft, the sales engagement platform that was acquired by Vista in 2022 for $2.3BN. Prior to Salesloft, Steve was Group Vice President of Enterprise at Yext and before that was a Senior VP @ InsideSales.com.

In Today's Episode with Steve Goldberg:

1. Becoming a Sales Leader:

• When did Steve first fall in love with sales?
• Why does Steve believe sales is more psychology than anything else? What can sales reps do to master the psychology of their prospects?
• What does Steve know now about sales that he wishes he had known in the beginning?

2. How to Close Prospects Faster Than Ever:

• How does Steve build relationships with prospects very fast? What questions does he ask?
• How does Steve know if he is really speaking to a buyer? What are the signals?
• How does Steve advise sales reps on getting multiple relationships within an account to prevent the potential of losing your champion?
• How does Steve feel about discounting? When is the right time to do it?

3. How To Do The Best Deal Reviews:

• What makes good vs great deal reviews? Who is invited? Who is not?
• Who sets the agenda? Who is responsible for what?
• How do deal reviews change throughout the quarter and throughout the year?
• Is a deal slipping into the next quarter an acceptable excuse for a sales rep to give?

4. How to Ensure Renewals in a World When They are Not Guaranteed:

• Have all budgets centralized back to the control of the CFO?
• Are people right to say that no CFOs are buying new technology today?
• What is the best way to show to customers the value you provide?
• Why does Steve believe revenue operations is the most valuable role within an org?

Sam Corcos is the Co-Founder & CEO @ Levels, the company helping you see how food affects your health with data from biosensors like continuous glucose monitors (CGMs). To date, Sam has raised over $89M for Levels from the likes of a16z (Jeff Jordan sits on his board), Founder Collective, Breyer Capital and Shrug Capital to name a few. Prior to Levels, Sam founded two prior companies, CarDash; a Y Combinator company that makes automotive repair and maintenance convenient. Before Cardash, Sam founded, Sightline Maps, an intuitive platform for 3D printing and visualizing topographical maps, marketed primarily towards the U.S. military.

In Today's Episode with Sam Corcos:

1. The Founding Moment:

• What was the a-ha moment for Sam with the founding Levels?
• What were the big mistakes Sam made with prior companies that he did not take with him to Levels?
• What does Sam know now that he wishes he had known when he started Levels?

2. How to Fundraise Like a Pro:

• Why does Sam believe that founders should take as many meetings with VCs as possible?
• What are the biggest mistakes founders make when meeting investors?
• Should founders meet with associates in the fundraising process?
• What does Sam mean when he says, "you have to create theater" when pitching?

3. How to Extract the Most Value from Your Investors:

• What have been Sam's biggest lessons on how to put your investors to work?
• What is the right and most strategic way to ask investors for specific help?
• How can founders create a competitive environment where VCs are competing to help?
• Which investors have been the most helpful?
• Why are post-IPO operators the best angels to have as investors?
• How has the a16z platform team been such a needle mover?

4. How to Find Your Partner and Master Parenting:

• What does Sam mean when he says he had a "one pager" in what he wanted in a partner?
• What was in the one-pager? How did dates respond?
• What are the biggest mistakes people make when dating?
• What is Sam most nervous about on becoming a parent?
• How does Sam think having a child will impact his marriage?

Sanjit Biswas is the Founder and CEO @ Samsara, allowing businesses that depend on physical operations to harness Internet of Things (IoT) data. Over the last 8 years, Sanjit has scaled Samsara to $1BN in ARR and a public company with tens of thousands of customers. Before Samsara, Sanjit was the CEO and co-founder of Meraki, one of the most successful networking companies of the past decade. Sanjit grew Meraki from his Ph.D. research into a complete enterprise networking portfolio. Meraki's sales doubled every year from inception and in 2012, Cisco acquired Meraki for $1.2 billion. Huge thanks to Doug Leone for some fantastic question suggestions pre this episode.

In Today's Episode With Sanjit Biswas We Discuss:

1. From Founding to $1BN in ARR in 8 Years:

• What was the founding a-ha moment for Sanjit with Samsara?
• Sanjit sold his prior company Meraki for $1.2BN, what worked with Meraki that Sanjit took with him to Samsara? What did not work that he left behind?
• What does Sanjit know now that he wishes he had known when he started Samsara?

2. The Man Who Found Product Market Fit Time and Time Again:

• What is the one single moment that Sanjit believes you know you have product market fit?
• What are the biggest mistakes founders make when chasing product market fit?
• How does being a bootstrapped company change how a company approaches chasing PMF?

3. Mastering a Multi-Product Company:

• How do you know when it is the right time to launch a second product?
• Does the second product have to make the first product better?
• What are the biggest mistakes companies make when going multi-product?

4. The Art of Great CEOship:

• Does Sanjit believe that the best CEOs are the best capital allocators?
• What has been the single best and single worst capital allocation decision in Samsara's journey?
• What are the biggest mistakes Sanjit has made in leadership? How did he learn and grow from them?

Geoff Charles is the VP of Product at Ramp, leading the product management, operations, and support teams. Prior to Ramp, Geoff helped spin off Mission Lane and scale credit products to millions of consumers. He started his career advising Fortune 100 financial services companies.

In Today's Episode with Geoff Charles We Discuss:

1. How to Become a Product Leader:

• How did Geoff make his way into the world of product?
• What are the single most important skills for product people to learn early?
• What are the biggest mistakes that product people make early in their career?

2. When and Who to Hire for the First Product Team:

• When is the right time to hire your first product people outside of founding team?
• Why are the best product teams in the early days professional services teams?
• What is more important; the person has stage or sector experience, when joining?
• Should you hire senior product people or junior product people as the first hires?

3. How to Increase Velocity Using Sprints:

• How does Geoff and Ramp use two-week sprints to have insane product velocity?
• How are they structured? How are goals set? Who is included?
• What makes a good vs a bad sprint? How is accountability tied to sprints?
• When do two-week sprints no longer become possible? What happens then?

4. Going Multi-Product, Will Incumbents Kill You and Product Re-Usability:

• When is the right time to add a second product?
• What are the biggest mistakes companies make when going multi-product?
• Why is it unlikely that an incumbent is the one to kill you? What competitor should worry you?
• What does Geoff mean when he speaks of "product re-usability"? Why is it crucial to velocity?

Tooey Courtemanche, Jr. is the Founder, CEO, President, and Chairman of the Board of Procore. He founded Procore in 2002 with a mission to connect everyone in construction on a global platform. After 13 years of business, the company had just $9.6M in revenue, 8 years after that they have over $890M in revenue. Under his leadership, Procore has grown to become a leading global provider of construction management software, connecting over 2 million users across 150+ countries. Today Procore trades on the New York Stock Exchange under the ticker PCOR. Huge thanks to Brian @ Bessemer and Will @ Iconiq for some amazing question suggestions today.

In Today's Episode with Tooey Courtemanche:

1. The Founding of a $8.5BN Company:

• How did Tooey's wife, Hilary and their house-building lead to the idea for Procore?
• What does Tooey know now that he wishes he had known when he started?
• Did Tooey always know he would be a success? What was the moment of most doubt?

2. The 13-Year Journey to $9.6M in Revenue:

• Why did it take so long to hit the $10M revenue mark? What changed in 2015?
• What is Tooey's biggest advice to founders and investors who face market timing risk?
• Why was Tooey laughed out of VC offices in 2008? What are his biggest pieces of advice to founders raising from VCs today?
• How does Tooey advise founders on the balance between vision and sticking to a mission vs realising when it is not working and giving up?

3. The Art of Great CEOship:

• What advice did Tobi @ Shopify give Tooey on being a great CEO? How did it impact his approach?
• What are the biggest differences between the reality of being a CEO and the Instagram version?
• What have been Tooey's biggest lessons on hiring? Why does hiring smart, ambitious but not humble people never work?
• Why does Tooey believe the idea of "becoming an entrepreneur" to be BS?

4. Parenting, Money and Marriage:

• Why does Tooey believe great parenting is like great CEOship?
• How does one bring up children to be ambitious and humble in a very privileged upbringing?
• What are the secrets to being there as a husband while also being a rockstar CEO?
• How does Tooey reflect on his own relationship to money and wealth today?

Dominik Richter is the Founder & CEO @ HelloFresh, one of the largest direct-to-consumer businesses of the last decade and the #1 recipe box delivery service. Fun fact, two of the three biggest cooking facilities in North America are HelloFresh facilities with the third being Disney World Orlando. Dominik has made over 40 angel investments in the EU and the US.

In Today's Episode with Dominik Richter We Discuss:

1. The Founding of One of the Largest D2C Companies:

• How did Diminik's dreams of being a footballer translate to founding HelloFresh?
• What does he know now that he wishes he had known when he started?
• Why does Dominik respect the brands that large banks have built?

2. To Raise or Not to Raise:

• Why does Dominik believe when you raise VC, you either have to sell or go public?
• What are the single biggest differences between raising in the US vs Europe?
• What are Dominik's biggest pieces of advice to founders raising today?
• Why does Dominik believe so many of the D2C companies should not have raised venture funding?

3. The IPO: When, How and Why:

• Why did Dominik decide to IPO the business so early?
• Why does Dominik believe that the first-day trading price is irrelevant?
• Why does Dominik believe that timing is so important when going public?
• What are the biggest pros and cons of being public?

4. The Rise and Fall of D2C:

• D2C has been crushed lately, why? Is this the end of D2C as a category?
• Is D2C an investable category for VC? HelloFresh is one of the biggest and $2.5BN market cap?
• What have been the best and worst resource allocations Dominik has made?
• Do recessions help or hurt recipe box businesses?

Guillaume Cabane is a growth advisor to high-growth SaaS Startups, including Ramp, Spot, Airbyte, G2, Gorgias, Metadata, Madkudu, and others. Guillaume held VP of Growth roles at Drift, Segment, and other successful startups, where he helped them grow from ~50 to 300. Prior, Guillaume spent 6 years at Apple.

In Today's Episode with Guillaume Cabane We Discuss:

1. Entry into Growth:

• How did Guillaume make his way into the world of growth?
• What are 1-2 of his biggest lessons from him time at Segment where he 4x revenue?
• What does Guillaume know now that he wishes he had known when he entered growth?

2. Enterprise vs SMB & CAC/LTV:

• Why does Guillaume think it is harder to go enterprise down than SMB up?
• What are the biggest mistakes companies make when scaling into enterprise?
• What are the biggest mistakes startups make with product-led-growth motions?
• Why does Guillaume believe it is impossible to analyse CAC/LTV in early companies?

3. Activation, Engagement and KPI Setting:

• What are the biggest mistakes companies and teams make in activation?
• What can growth and marketing teams do to guarantee engagement in prospects?
• Why are all KPIs not tied to revenue BS?

4. Hiring the Growth Team:

• What are the core characteristics of great growth hires?
• How quickly does it become apparent when you have made a bad growth hire?
• Why do founders make the best profiles when hiring your first growth hire?
• What are the biggest mistakes Guillaume has made when hiring for growth?

5. Why Growth is Like Venture:

• What is the secret to building a great growth portfolio?
• Why is it impossible to scale to $50M ARR with only one good channel?
• What is the right way to spread resources across channels?
• When is the right time to add new channels and diversify?