Peter Wagner is a Founding Partner of Wing. Peter has led investments in dozens of early-stage companies including Snowflake, Gong, Pinecone, and many others which have gone on to complete IPO's or successful acquisitions. Prior to founding Wing, Peter spent an incredible 14 years at Accel, starting as an associate in 1996 and scaling to Managing Partner, before leaving to start Wing.

In Today's Episode with Peter Wagner We Discuss:

1. From Associate to Managing Partner to Founding Partner:

• How did Peter first make his way into the world of venture as an associate at Accel?
• How important does Peter believe it is to have early hits in your career as an investor?
• What is the biggest mistake Peter sees young VCs make today?

2. The Venture Market: What Happens Now:

• Does Peter agree with Roger Ehrenberg that venture returns will worsen moving forward?
• How does Peter answer the question of how large asset management venture firms co-exist in a world of boutique seed players also?
• Does Peter agree with Doug Leone that "venture has transitioned from a high-margin boutique business to a low-margin, commoditized industry?

3. Investing Lessons from 27 Years and Countless IPOs:

• What have been some of Peter's single biggest investing lessons from 27 years in venture?
• Why is Peter so skeptical of capital-intensive businesses? Will defense and climate startups suffer the same fate as clean tech did in the 2000s?
• How does Peter reflect on his own relationship to price? When does it matter? When does it not?
• What have been Peter's biggest lessons on when to sell positions vs when to hold?
• What has been Peter's biggest miss? How did it impact his mindset?

4. Building a Firm from Nothing:

• How was the fundraise process when leaving the Accel machine and raising with Wing?
• What have been the single hardest elements of building Wing? What did he not expect?
• What advice does Peter have for someone wanting to start their firm today?

Nicolai Tangen is the CEO of Norges Bank Investment Management, the largest sovereign wealth fund in the world with $1.55 Trn in assets, owning on average, 1.5% of every listed company. Tangen was previously Chief Executive Officer and Chief Investment Officer in AKO Capital, which he founded in 2005. Prior to this, Tangen was a partner and senior analyst at Egerton Capital and an equity analyst at Cazenove & Co.

In Today's Episode with Nicolai Tangen We Discuss:

From Religious Town in Norway to Leading the Largest Sovereign Wealth Fund:

• What was Nicolai like as a child? How would his parents have described him?
• Why does Nicolai think that loners have a greater chance/ability to make money?
• What does Nicolai know now that he wishes he could tell a 20-year-old Nicolai?

The Top 10 Questions:

1. US Tech Firm Concentration: Is Nicolai concerned by the concentration of enterprise value in US tech firms? Have incumbents ever been as strong as they are today?

2. Impact of AI: What does Nicolai believe the impact of AI will be on society and productivity? What is his approach to investing in it moving forward?

3. Bitcoin: Why does Nicolai not want to hold Bitcoin? Why does he not understand it?

4. China: What would need to happen for China to be investable? How will the China situation play out?

5. Europe: Does Nicolai believe Europe is so far behind the US? Why? What can we do to improve?

6. Climate Change: How does Nicolai approach investing in climate? What works? What does not?

7. Sam Altman: Would Nicolai invest in Sam's new $7Trn project? What are some of Nicolai's biggest lessons from the time he has spent with Sam?

8. Investment Psychology: How does Nicolai retain a neutral investor psychology? How does he not get too up when doing well and too low when not doing well?

9. Investing Lessons: What are Nicolai's biggest investment hits and misses? What did he learn from them?

10. The Future: Why is Nicolai so optimistic about the future? What is he concerned about? How will we overcome our greatest challenges?

Frank Quattrone is the Founder and Executive Chairman of Qatalyst and served as its CEO from the Firm’s founding until January 2016. Over more than four decades, Frank and the teams he has led have advised on more than 600 mergers and acquisitions with an aggregate transaction value over $1 trillion and on more than 350 financings that raised over $65 billion for technology companies worldwide. Frank led the IPOs of Amazon.com, Cisco, Intuit, Netscape, among many others. He advised Apple on its $400 MM acquisition of NeXT (which led to Steve Jobs’ return to Apple); Concur on its $8.3B sale to SAP; LinkedIn on its $28.1B sale to Microsoft; Qualtrics on its $8B sale to SAP and Twitch on its $1B sale to Amazon.com.

In Today's Episode with Frank Quattrone:

1. Has Regulation Killed M&A:

• Why does Frank disagree that regulation has killed M&A?
• What is the real reason why M&A is so down at present?
• What would impact would a Trump administration have on the M&A environment?
• What are some of Frank's biggest lessons from 600 prior transactions over dour decades of what happens when an M&A market shuts down?

2. When Will the IPO Window Re-Open:

• Does Frank agree that the IPO window is currently closed for tech companies?
• How does this IPO window compare to the dot com bust and 2007?
• What is needed for the IPO window to re-open?
• What is the timeline that Frank puts on the IPO window opening again?

3. M&A: How Do Companies Get Bought:

• What is the process for a company to be bought?
• What are the single biggest mistakes the seller makes in the process?
• What do the best buyers and sellers do to get the best price?
• Does Frank agree with the notion that "companies are bought and not sold"?

4. IPOing Amazing, Selling Linkedin and Qualtrics:

• What is the story behind, Frank, Bill Gurley, Jeff Bezos and John Doerr pricing the Amazon IPO?
• How did Linkedin come to be bought by Microsoft? What did that process look like?
• How did Frank structure an event to ensure that Ryan @ Qualtrics and Bill McDermot @ SAP would meet and lead to the acquisiiton?

Sami Inkinen is the Co-Founder and CEO of Virta Health, the company reversing type 2 diabetes. Before Virta, Sami was the Co-Founder of Trulia, steering the company to a successful IPO and its eventual sale to Zillow Group. Outside of the boardroom, he launched Fat Chance Row, a daring venture to row 2,750 miles across the Pacific, unsupported with his wife, rowing 18 hours straight per day.

In Today's Episode with Sami Inkinen:

1. From Farm in Finland to IPO Founder: Relationship to Money

• How did Sami's humble upbringing on a farm in Finland impact his early mindset and ambition?
• How does Sami analyze his relationship to money today? How has it changed over time?
• Why was the two weeks following Trulia's IPO the worst two weeks of his life?

2. The Secret to Marriage: Rowing 2,750 Miles Together:

• What are some of the biggest lessons on marriage Sami has from spending 45 days rowing the Pacific with only his wife for company?
• What was their single biggest argument over the 45 days? What did Sami learn from it?
• Sami worked with his wife, what are the biggest pros and cons of working with your spouse? Would Sami recommend it?
• What does Sami believe are the core fundamentals that underpin the best marriages?

3. The Secret to Parenting: The Regret of Delegation:

• What is Sami's biggest regret when it comes to parenting?
• How does Sami think about what it means to be a great father today? How has that changed?
• How did Sami's relationship with his wife change when they had kids?

4. Relationship to Identity:

• Why does Sami believe tieing your identity to the company, as a founder, is so dangerous?
• How does Sami advise on creating multiple personas to prevent this?
• Why does Sami believe that all the best founders are addicts to some extent?

Justin is the Founder and Managing Partner of one of the nation’s best-performing private equity firms, Shore Capital Partners (“Shore”). Since the firm’s inception in 2009, Shore has grown from 4 to over 140 team members managing over $6 billion in AUM, representing 900+ acquired companies and more than 33,000 employees. Shore is also one of the most active private equity firm in the world by deal volume according to PitchBook while continuing to achieve return profiles that rank Shore among the top 1% of private equity firms. Justin is an avid sports fan/investor and is the Alternate Governor for the Phoenix Suns (NBA), Phoenix Mercury (WNBA) and Nashville SC (MLS). 

In Today's Episode with Justin Ishbia:

1. From Law Student to Founding Shore Capital:

• How did seeing Justin's father operate impact how he thinks about building Shore today?
• What does he know now that he wishes he had known when he started Shore?
• How important a role does luck play in success? How has his mindset changed on this?

2. How to Make Top 1% PE Returns:

• Why does Justin see private equity done well like "using a flashlight in a dark room"?
• What are the top 3 elements that Justin looks for in all acquisitions they make at Shore?
• When did Justin think there was an advantage of scale/network effect but was proved wrong?
• How does Justin think about downside protection and risk mitigation?
• Why does Justin like to back and invest in first time founders more than any other type?

3. Building World-Class Investing Teams:

• Why does Justin believe the best companies are talent systems?
• How does Justin structure the talent system at Shore to ensure consistent incredible talent?
• What does Justin believe are the three traits required to win in private equity?
• What question does Justin ask all potential CEOs he hires for acquired companies?
• What has Justin learned is the single clearest sign of the top .1% talent?

4. Justin Ishbia: The Family Man and Husband:

• What metric does Justin use to track whether he is being a good and present father?
• Is it possible to be top 1% and have balance with a wife and family?
• What does "great fatherhood" mean to Justin? How has his thoughts on this changed?
• How does Justin think about bringing kids up in a world of immense privilege and ensuring they remain ground and ambitious?

Scott Williamson was most recently Chief Product Officer for GitLab, where he led a team of 65 in Product Management, Product Operations, Growth, Pricing, and Corporate Development functions.  Before GitLab, Scott was VP of Product for SendGrid for over six years, where helped lead the company to a successful IPO and $3B acquisition by Twilio. 

In Today's Episode with Scott Williamson We Discuss: 

1. From Sales to Product Leader:

• Why does Scott believe sales is a great starting point for product people?
• To what extent does an MBA help someone wanting to pursue a career in product management?
• What does Scott know now that he wishes he had known when he started his career in product?

2. What, Who, When: How to Build a Product Team:

• Is product management art or science? What is the ratio?
• What are the four core roles of a product manager today?
• When is the right time to hire your first PM?
• What is the ideal profile for this first PM hire?
• What are the single biggest mistakes founders make when hiring PMs?

3. Hiring the Best Product People:

• What does Scott's hiring process look like for all new product hires?
• How does Scott test for systematic thinking and problem-solving ability?
• What questions does Scott always ask in interviews?
• What are the best case studies to use to test a candidate's skill set?
• How important is it for the candidate to have domain expertise in your product category?

4. The Best Product Teams are the Best Writers:

• What are the two different types of documents that product teams must use?
• How do you know when to use a one-pager vs a six-pager?
• How does the discussion and planning cycle for the different documents differ?
• How important is it for PMs to be great writers also?

Roger Ehrenberg is a legend of the venture industry as the Founder of IA Ventures, among the most successful seed-stage venture firms of this generation, having seeded companies including Datadog (NASDAQ: DDOG), Digital Ocean (NYSE: DOCN), The Trade Desk (NASDAQ: TTD) and Wise (LSE: WISE.L). Today Roger is the Founder and Managing Partner of Eberg Capital, a pioneer in bridging the gap among sports franchises, sports betting, media and entertainment. Roger’s current sports investments include stakes in the Miami Marlins, Real Salt Lake, Alpine Racing, Betr, Commonwealth, Kero Sports, Simplebet, SlamBall, Smarkets and WagerWire.

In Today's Episode with Roger Ehrenberg We Discuss:

1. The Commoditisation of Venture and Worsening Returns:

• Why does Roger disagree with Doug Leone that "we have moved from a boutique high margin business to a commoditised low margin industry"?
• Why does Roger believe we will see consistently worsening returns in venture?
• Is this influx of LP capital cyclical or is it here to stay?

2. The New LPs and The Broken Existing LP World:

• Why does Roger think the existing incentive structure for LPs is totally broken?
• Who are the most important new LPs entering the venture market?
• How do sovereigns and pension funds entering venture change the industry?
• Which players have capitalised on this new LP class best?

3. Where Does the Liquidity Come From:

• With the closed IPO window and lack of M&A, where will liquidity come from in the next 24 months?
• Would a Trump administration open M&A markets? Does Roger agree M&A markets are shut down?
• When does Roger believe IPO markets will open again? Will Databricks and Stripe go out in 2024?
• If Roger were to run a continuity fund strategy, how would he structure it? What would he do?

4. When to Sell and When to Hold:

• How does Roger advise managers on when to sell vs when to hold?
• How important is it for a new firm to have a company go public in the first five years?
• What are Roger's biggest lessons from selling The Trade Desk at a $2.5BN valuation?
• How does Roger think about managers thinking they should manage the public book of their portfolio for their LPs? What are the pros and cons?

5. Relationship to Money:

• Do rich investors make better investors? How does investing when you have a lot of cash already change your mindset around investing and exiting?
• How does Roger analyse his relationship to money today?
• What have been the single biggest needle movers in his wealth journey? How did it feel when he made a $6M bonus?

6. The Secrets to Parenthood and Marriage:

• What does it mean to be a great father for Roger?
• How does Roger think about bringing his children up with the same level of hunger and ambition, despite being brought up with such wealth?
• What are Roger's two biggest lessons on the secret to a great marriage?

Christian Hecker is the Founder and CEO of Trade Republic, the company making it easy and inexpensive for everyone with a smartphone to invest. To date, Christian has raised over $1.3BN for the company from the likes of Sequoia, Founders Fund, Accel and Creandum to name a few. Previously, Christian worked in Bank of America Merrill Lynch’s Investment Banking department.

Johan Brenner is a General Partner at Creandum. Johan has led Creandum’s investments in iZettle (acquired by PayPal for $2.2bn in 2018), Trade Republic, Klarna, Pleo, Neo4J, Vivino and more. Johan was previously a repeat entrepreneur, founding one of the first online brokers in Europe in 1997 (sold to E*TRADE in the US), then JobLine (sold to Monster), Bookatable (Michelin) and Tradera (Ebay).

In Today's Episode with Christian Hecker and Johan Brenner We Discuss:

1. Selling 75% of Trade Republic for €600,000:

• How did Christian come to sell 75% of Trade Republic for €600K?
• How did Johan and Creandum solve this challenge when they invested?
• What are some of Christian's biggest pieces of advice on cap table construction?

2. Raising $1.3BN From the Best Investors in the World:

• What are Christian's biggest fundraising lessons from raising $1.3BN from the best in the world?
• How did Doug Leone and Sequoia come to lead Trade Republic's round? What was the meeting with Doug like? What questions did he ask? How did it go?
• How important of a skill does Johan believe being a great fundraiser is for founders?

3. Scaling into Europe's Next Decacorn:

• What are the single biggest issues that arise when scaling so fast? What breaks first?
• Does CAC increase with time or decrease?
• Why did Christian decide to stop paid marketing on Google and Facebook and stop spending $100M+ there overnight?
• Why is Christian so bullish on influencer marketing? What works? What does not work?

4. Europe: A Hub for Innovation or a Retirement Home:

• Does Christian believe that young people in Europe work hard enough?
• What are the biggest challenges to scaling teams in Europe?
• Why does Johan believe the biggest challenge in Europe is the lack of exit markets?
• What can Europe do to improve and increase our chances of being successful?

Martin Gontovnikas, a.k.a Gonto, is a software engineer at heart who moved to the “dark side” to focus on Marketing. With this career transition, he found a way to combine his 2 passions by applying his “engineering thinking” model to Marketing. He is now a B2B SaaS Advisor to Vercel and Airbyte among others and Co-Founder & GP of Hypergrowth Partners. Previously, he was SVP of Marketing and Growth at Auth0.

In Today's Episode with Martin Gontovnikas (Gonto) We Discuss:

1. From No Idea to Growth Leader:

• How Gonto made his way into the world of growth when it was not a thing?
• What does Gonto know now that he wishes he had known when he entered the world of growth?
• Why does Gonto believe product and marketing is more important than sales and marketing?

2. Growth: What, When and Who:

• What is growth? What is it not? What do people misunderstand most with growth?
• When is the right time to hire your first growth person?
• What is the right profile for the right first growth hire? Junior? Senior?

3. Mastering PLG and Enterprise:

• What are the single biggest mistakes startups make when scaling into enterprise?
• Why does Gonto believe that all PLG companies should start with 6-8 design partners?
• Is it possible to do enterprise and PLG at the same time?
• How does one provide enough value in a PLG motion to convert enterprise buyers?

4. Data vs Intuition: Art vs Science:

• Is growth more art or science?
• Why does Gonto believe qualitative data is more important than quantitative?
• How does Gonto think about psychology when selling and marketing? What do so few startups? understand about the psychology of their customers?
• How does Gonto approach messaging and what is truly great product marketing?

Thomas Plantenga is the CEO @ Vinted, one of the fastest-growing marketplaces in the world with a valuation of $4.5BN. Prior to becoming CEO, Thomas worked with a range of organisations including Bookaboat, OLX, Sellit/Wallapop and FJLabs.

Alex Taussig is a General Partner @ Lightspeed and co-leads the fund's Consumer investment team. Alex's portfolio includes the likes of All Day Kitchens, Archive Resale, Daily Harvest, Faire, Found, Frubana, Keychain, Kikoff, Vinted, YaySay, and Zola.

In Today's Episode with Thomas Plantenga and Alex Taussig We Discuss:

1. The CEO Who Did Not Want to be CEO:

• How did Thomas come to be CEO @ Vinted? Why did he not want the job at first?
• What does Thomas know now that he wishes he had known when he started?

2. The Mechanics of the Fastest Growing Marketplace:

• What is the single most important metric for Vinted?
• How does Vinted determine what market to open next? What do they look for?
• How does Vinted think about depth vs breadth in each country?
• What is the AOV today? How does it vary by country?
• How long does it take for each country to be cash flow positive?

3. The Biggest BS in Startups: Rule of 40 and EBITDA:

• Why does Thomas think VC's obsession with "Rule of 40" is BS?
• Why does Thomas believe EBITDA optimization is BS and useless?
• What are the hardest elements of scaling a marketplace that no one knows?

4. The Bull, Bear and Investor Approach to Vinted:

• Alex, what was Lightspeed's pre and post-mortem when investing in Vinted?
• How does Lightspeed analyze TAM and market sizing when investing?
• What was Lightspeed's single biggest concern when investing in Vinted?

5. Europe: A Hub of Innovation or a Retirement Home:

• Does Thomas believe that European young people have a worse work ethic than those in the US?
• Is Thomas concerned by the state of regulation hampering innovation in Europe?
• What can be done to improve work ethic and the state of regulation today?
• Why is Alex and Lightspeed more bullish than ever on Europe today?

Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world’s most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more.

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. 

Geoff Lewis is a Founder and Managing Partner of Bedrock, one of the breakout and new venture firms of the last decade, famously in search of narrative violations. He serves or has served on the Board of Directors for companies including Lyft (NASDAQ: LYFT), Nubank (NYSE: NU), Epirus, and Vercel. 

Bill Ackman is the CEO of Pershing Square Capital Management, L.P., an SEC-registered investment adviser founded in 2003. Pershing Square is a concentrated research-intensive fundamental value investor in long and occasionally short investments in the public markets.

Martín Escobari is Co-President, Managing Director and Head of General Atlantic’s business in Latin America. Martín is Chairman of the firm’s Investment Committee and also serves on the Management and Portfolio Committees.

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo’s early entry into software buyouts and built the firm into one of the top private equity firms in the world. 

In Today's Episode on Price Sensitivity We Discuss:

1. Doug Leone: Why the attitude of "deploy, deploy, deploy will get so many in trouble"?
2. Marcelo Claure: How to know when price matters and when it does not?
3. Geoff Lewis: What is the right framework to assess price at an early stage?
4. David Tisch: How does the importance of price change vis a vis company vs portfolio?
5. Orlando Bravo: What have been Thoma Bravo's biggest lessons on price?
6. Cyan Banister: Why does Cyan believe there will be a reckoning?

Erik Allebest is the CEO @ Chess.com, the #1 online chess service on the planet with more than 150+ million members and 15+ million games played each day. Erik has scaled the company to over 700 people and $100M+ in revenue with no venture funding.

In Today's Episode with Erik Allebest:

1. From Unemployable to $100M+ Revenue Founder:

• How did Erik make his way into the world of tech and startups?
• Was his MBA worth it? How does he advise others on whether to get one or not?
• What does Erik know now that he wishes he had known when he started?

2. Scaling to $100M Revenue with No Venture Funding:

• Why did no one want to invest in Chess.com in the early days?
• What did Erik do differently as a result of not raising any venture funding?
• What would Erik have done if he had money from the start?
• What are Erik's biggest pieces of advice to founders with funding today?

3. Hard Lessons Scaling to 150M Members:

• What are 1-2 of Erik's biggest lessons on how to scale users with zero budget?
• What customer acquisition worked? What did not work?
• How important was COVID and The Queen's Gambit to memberships and sign-ups?
• What are the single biggest mistakes Erik sees founders make on customer acquisition today?

4. Parenting, Marriage, Metrics and Money:

• Why does Erik not care about money or capitalism today?
• How has Erik's style of parenting changed over the years? What works? What does not?
• What does Erik believe is the secret to marriage? What have been his biggest lessons?
• Why does Erik hate metrics? If so, how does he run the business towards goals and output?

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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?