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?

Keith Rabois is a General Partner @ Founders Fund, one of the world's best venture funds with a portfolio including the likes of Facebook, SpaceX, Anduril, Tesla and many more. For the last 23 years straight, Keith has either invested in or founded a $BN company. Keith is also the Co-Founder and CEO @ Openstore, the company that will buy or run your Shopify business.

Mike Shebat is the Founder and CEO @ Traba, the company providing industrial staffing when and where you need it. To date, Mike has raised $49M with Traba from some of the best including Founders Fund, General Catalyst and Khosla Ventures.

In Today's Episode We Discuss:

1. What it Takes to Build a Great:

• Why does Mike expect everyone to work in office 12 hours per day, 4 days per week?
• At what point does an extra hour of work not lead to more output?
• What are the expectations in terms of emails, out of office, the weekends?
• Keith, from the 23 BN companies you have worked with, is this insane work ethic aligned to all of them? Which had it? What did not?
• What core components of PayPal's work ethic made it so strong? What does Keith mean when he says Linkedin could and should have been 5x bigger?

2. The Hiring Process for the Swat Team:

• What does the hiring process look like for this type of work environment?
• What are the signs that someone is really aligned to it vs faking it for the interview process?
• What have been Keith's biggest lessons on both compensation and title in the hiring process?
• Why does Keith believe that culture is like concrete? What are the biggest mistakes he has made on culture and what would he have done differently?

3. First-Time Founders, Innate Entrepreneurs & Europe's Failing:

• Does Keith agree the best founders always show signs of early entrepreneurship in their teens?
• Why does Keith prefer first-time founders to serial entrepreneurs? Why are they better?
• Why does Keith believe that Europe has not created a $100BN company since 1990?

4. Remote Work, Network Effects and Baseball:

• Why does Keith believe being great in venture is like baseball?
• Why does Keith and Founders Fund not invest in remote teams? How does he explain Gitlab?
• Why does Keith believe Airbnb has the best network effect he has ever seen?

Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support.

Yann LeCun is VP & Chief AI Scientist at Meta and Silver Professor at NYU affiliated with the Courant Institute of Mathematical Sciences & the Center for Data Science. He was the founding Director of FAIR and of the NYU Center for Data Science. 

Emad Mostaque is the Co-Founder and CEO @ StabilityAI, the parent company of Stable Diffusion. Stability are building the foundation to activate humanity’s potential.

Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC.

Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, just announced last week, Theory is a $230M fund that invests $1-25m in early-stage companies that leverage technology discontinuities into go-to-market advantages.

Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses.

Cris Valenzuela is the CEO and co-founder of Runway, the company that trains and builds generative AI models for content creation. 

Richard Socher is the founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of AI startup MetaMind, acquired by Salesforce in 2016.

In Today's Episode We Discuss:

1. Foundational Models: Analysis

• Will foundational models become commoditized?
• Who are the major players? What are their different strengths?
• Who will win? Who will lose?
• How important is the size of the model vs the quality of the data?

2. Open vs Closed:

• What are the biggest pros and cons of an open ecosystem for LLMs?
• Why is it naive to think that open-source LLMs will prevail?
• What will determine which method wins?

3. An Analysis of the Incumbents:

• Why is Google the most vulnerable? What can they do to regain ground?
• Why is Apple the sleeping giant? How could they win the next wave of AI?
• What should Amazon do today to compete with Microsoft?

4. The Future: Doom and Gloom?

• Why is it ridiculous to assume AI systems want to dominate?
• Why will AI create a renaissance of creativity and human freedom?
• What role should regulation play in the advancement and progression of AI?

Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC. Jeff previously served as Twitter's Head of Consumer Product, a position he came to following the acquisition of his prior company, Crashlytics. Today, Crashlytics is the de-facto mobile crash reporting solution for iOS and Android and runs on over 6 Billion monthly active smartphones worldwide.

In Today's Episode with Jeff Seibert We Discuss:

1. The Art of the Pivot:

• What are Jeff's biggest pieces of advice to founders pivoting?
• How do you know when you have enough data to make the decision to pivot?
• What are the single biggest mistakes founders make when pivoting?

2. AI: Who Wins and Who Loses:

• Why does Jeff believe that OpenAI will transition into an infrastructure play?
• What are the most significant challenges OpenAI will face moving forward?
• Why does Jeff believe that Apple are best positioned to win in an AI world?
• Why does Jeff believe that Google are the most vulnerable incumbent?
• What would Jeff do if he was CEO of Google?

3. LLMs: What Happens Now:

• Will we see the commoditization of LLMs?
• What are the biggest misconceptions people have on training and fine-tuning LLMs?
• Will we see LLMs increasingly specialise to vertical-specific models or will they remain horizontal?
• What is the difference between a thick and a thin wrapper when building on top of LLMs?

4. Angel Portfolio in Review:

• How many angel checks has Jeff written? How many failed? How many home runs?
• Does Jeff believe that company valuations are being kept artificially high?
• How did Jeff make 200x selling through the secondary market for a now failing company?
• What are Jeff's three biggest pieces of advice for angels today?

Matteo Franceschetti is the Co-Founder and CEO @ Eight Sleep, a company dedicated to fueling human potential through optimal sleep. To date, Matteo has raised over $160M for the business from the likes of Founders Fund, Ryan Petersen, Naval Ravikant, Kevin Hart, AROD and many more.

In Todays Episode with Matteo Franceschetti We Discuss:

1. Why Did Sleep Need "Solving":

• Why did Matteo decide he wanted to spend decades of his life-solving sleep?
• If Matteo has known how hard it was going to be, would he do it again?
• What does Matteo know now that he wishes he had known at the start of the journey?

2. Hiring the Best Team:

• What is Matteo's playbook for hiring?
• What are the five questions that Matteo asks in every interview?
• What are big red flags? What are strong signals of great talent?
• If people have been let go in a RIFF, is that a concern?
• How does Matteo construct hiring panels? What vote count is enough for an approved hire?
• What are Matteo's biggest lessons on title and pay a new hire receives?
• What are some of Matteo's biggest lessons when it comes to firing people?

3. Funding the Business:

• What was the hardest round to raise? Why?
• Are investors justified in their skepticism of hardware?
• What are the single biggest pieces of advice Matteo would give to founders on raising?
• How impactful has it been having Keith Rabois and Founders Fund as an investor?
• Do VCs really add value?

4. Mastering Health, Sleep and Nutrition:

• How does your diet impact the quality of sleep you have?
• How does exercise and the time of exercise impact your sleep?
• What are some common rules on sleep that are BS and myths?
• What are some of the most non-obvious truths about getting great sleep?

Rebecca Kaden is a Managing Partner @ Union Square Ventures, one of the leading early-stage firms of the last decade with investments in Twitter, Twilio, Coinbase and many more.

Nicole Quinn is a General Partner @ Lightspeed where she has led investments or sits on the board of Calm, Cameo and LunchClub to name a few.

Eurie Kim is a Managing Partner @ Forerunner Ventures, the leading early-stage consumer fund. Eurie has led investments and sits on the board of Oura, The Farmers Dog, Curology and more.

In Today's Roundtable We Discuss:

1. Seed Rounds:

• Is it even possible for traditional seed funds to play in a world of multi-stage funds investing so aggressively at the seed stage?
• Is seed immune to the macro environment? Will seed pricing remain as high as ever?
• What advice does the team have for seed founders approaching a Series A? What do they need?

2. Series A:

• How is the Series A market looking today? Is there a crunch at the Series A?
• To what extent are valuations compressed at the Series A?
• What 3 core elements do companies at the A stage, looking for a Series B next, need to focus on?

3. Series B and Beyond:

• Is the real crunch at the Series B?
• Why are down rounds so much better than structured rounds for companies raising?
• Will we see a wave of M&A in the next 12 months?

4. Crypto, AI and Hot Takes:

• Why is now the best time to be investing in crypto?
• Why is investing in AI a lottery right now?
• What is the most controversial thing that each believes today?

Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support. Today Des leads all Intercom’s R&D efforts, and parts of Intercom’s marketing.

In Today's Episode with Des We Discuss:

1. From Consultancy to Founding a Unicorn:

• What was the founding a-ha moment for Des and the team with Intercom?
• Why does Des believe that most startup advice is BS and outdated in 5 years?
• What does Des know now that he wishes he had known when he started?

2. LLMs: The World is Not Equal:

• What does Des mean when he says the world of LLMs is not equal?
• How do the different LLMs very in quality, price and speciality?
• Does Des agree with Alex @ Nabla, "the best companies in the future will work with many LLMs at the same time and switch between them for different things"?
• To what extent does Des believe LLMs will be commoditised and it will be a race to the bottom?
• Would Des be a buyer of OpenAI at a $90BN price? Why not?

3. How to Survive in a World of OpenAI:

• What two simple questions will determine if Open AI will kill your existing business?
• What 3 criteria will determine if there is a new business to be built on top of OpenAI?
• What is the different between a thin layer on top of an LLM and a thick wrapper with real value?
• Which traditional incumbents are most vulnerable? What should they do in this new world?
• How long does it take for incumbents to really be impacted?

4. The Titans of Tech: Who Wins:

• Why does Des believe that Apple could be a massive winner in the next wave of AI?
• Why does Des believe that Google have not been impressive and failed to keep pace?
• Why does Des think OpenAI should be wary of Amazon? What could they do to threaten them?
• What opportunity does Facebook have here? How could Instagram and Whatsapp win?

5. Startup and Investing 101:

• Why does Des believe that every founder should write a blog post per week?
• Why does Des believe that most B2B marketing sucks? What makes great B2B marketing?
• What are Des' biggest lessons from the Hopin journey?
• How has Des' angel investing changed in the last year with the rise of AI?

Ryan Petersen is Founder & CEO @ Flexport, a leader in global supply chain technology. In 2022, Flexport moved more than $26 billion of merchandise. Over the last 10 years, Ryan has raised close to $2.5BN for the business with the latest valuation pegging the business at $8BN. Prior to starting Flexport, Ryan was the founder and CEO of ImportGenius, a premier provider of transaction data for the global trade industry.

In Today's Episode with Ryan Petersen We Discuss:

1. The Origins of a Generational Defining Leader:

• What did Ryan want to be when he was growing up?
• How did scooters and motorbikes in China lead to the idea for Flexport?
• What does Ryan know now that he wishes he had known when he started Flexport?

2. Speed and Money: The Secrets To Execution:

• Does Ryan believe speed is key to execution? What is the difference between speed and velocity?
• What advice does Ryan have to founders who raise a lot of money? How should it impact hiring?
• What are the most common ways founders become inefficient post-fundraising?
• Why does Ryan look to invest in founders with jaded pasts and a chip on their shoulder?

3. The Art of Resource Allocation:

• Are the best CEOs the best resource allocators?
• What is the single best resource allocation Ryan has made? What did he learn?
• What is the worst? What did he learn?
• What have been Ryan's biggest hiring mistakes? How did that change his approach?

4. The Wider World:

• Is Ryan long or short on China? Why?
• Will we see global trade become nationalized? Why?
• Will we see interest rates raised further? What impact does that have on trade?
• What has been the impact of war on trade and the shipping industry?

5. Ryan Petersen: The Father and Husband:

• How has having kids changed how Ryan approaches leadership and management?
• How does Ryan juggle 2 young kids and leading a 2,500 person company?
• How does Ryan retain romance with his wife while also being a full-on CEO of a large co?
• Does money make you happy? What does it help with? What does it not help with?

Chris Degnan serves as Snowflake’s Chief Revenue Officer and has been with the company since 2013. Starting as employee #13 and Sales employee #1, Chris built a go-to-market strategy from the ground up, driving sustained high growth and global reach. Under his sales leadership, Snowflake has grown its annual product revenue from $0 to over $1 billion. Prior to Snowflake, Chris served in Sales leadership roles at EMC and Aveksa, and worked in enterprise sales at Informatica and Covalent Technologies (acquired by VMware).

In Today's Episode with Chris Degnen We Discuss:

1. From SDR To World Leading CRO:

• How did Chris first make his way into the world of sales?
• What does he know now that he wishes he had known when he started in sales?
• What are the single biggest mistakes young sales people make today scaling their careers?

2. The Secret to Hitting Quota in Sales:

• Why does Chris believe all reps need to do 8 customer calls per week?
• How do the best sales reps approach sales prospecting today?
• Is cold outbound dead? How does Chris advise his teams on cold calls and emails?
• What are the best reasons reps should say no to customers?
• Should reps be discounting today? What is an acceptable level?

3. Sales and Product: The Most Important Relationship:

• Why does Chris believe sales and product is the most important relationship?
• What can leaders do to ensure sales and product communicate effectively?
• How does Chris use sales calls today both with his sales team and with product?
• What are the single biggest reasons comms between sales and product breaks?

4. Mastering Sales Leadership:

• How does Chris approach sales forecasting? What works? What does not work?
• Does Chris celebrate when quota is hit? How do you find the balance between pushing further and harder but also celebrating the wins?
• How do the best sales leaders train and develop their talent? What do the worst do?

5. Customer Success is BS: Professional Services for the Win:

• Why does Chris believe that customer succeed is BS and you should get rid of it?
• Why are professional services so much better?
• How should the org be structured then when removing CS and adding professional services?
• Who is then responsible for upsell?

Danny Cohen is the President of Access Entertainment, a division of Len Blavatnik's Access Industries. Access Entertainment’s corporate investments include film and television studio A24; Europe’s fastest-growing company Tripledot Studios; creator economy leader Spotter; and a new immersive arts’ experience launched in collaboration with David Hockney and Lightroom. Before joining Access, Danny was the Director of BBC Television where he had responsibility for all of the BBC's network channels and the greenlighting and production of the BBC's drama, entertainment, comedy, arts, history, science, educational content and documentary. 

In Today's Episode with Danny Cohen We Discuss:

1. From Leading the BBC to Investing for Len Blavatnik:

• How did Danny make his way from leading the BBC to investing for Len @ Access?
• What was he most nervous about when making the transition to investing?
• What has been the hardest investing skill to learn?

2. Great Founders are Like Great Actors:

• What are the biggest similarities in what makes the best founders and the best actors?
• How are the best founders different from the best actors?
• Why does Danny believe the risk that an actor takes is so different to the risk founders take?
• How does Danny feel both founders and actors can and should be managed?

3. The Future of Media:

• What does Danny mean when he says he looks for "eyeballs and attention" when investing?
• How does legacy media respond to the threat created by social media today?
• How does AI change the future of content creation and distribution today?
• How do the strikes in Hollywood impact the future of content supply?

4. Marriage, Children and Loneliness:

• Why does Danny believe that loneliness will continue to be the biggest problem we face?
• What are Danny's biggest pieces of advice from 17 years of happy marriage?
• Why did Danny decide to not have children? What did that decision-making process look like?

Joey Zwillinger is the Co-Founder & CEO @ Allbirds, the company behind the world's most comfortable shoe. In Nov 2021, Joey took the company public and the stock soared to an all-time high of $4BN, today the company has a market cap of $137M. Prior to Allbirds, Joey spent six years at biotechnology firm, Terravia, leading its renewable chemical business, developing and selling high-performance algae-based chemicals into various industries such as CPG, personal care, and industrials.

In Today's Episode with Joey Zwillinger We Discuss:

1. The Founding Moment:

• How did Joey's wife's friendship lead to the co-founding of Allbirds?
• What does Joey know now that he wishes he had known at the founding moment?
• What does Joey believe he is running away from? What is he running towards?

2. Public Market Performance Review:

• Why has Allbirds lost 97% of it's value since going public? What mistakes were made?
• Why has revenue declined for the first time this year?
• What strategic investments have Allbirds pulled back on or paused entirely?
• When will Allbirds be profitable?

3. The Competition:

• How do Allbirds compete and catch up with On and Hoka?
• What strategic mistakes did Allbirds make in COVID that allowed others to take the crown?
• Was the movement into running and athletics a mistake for Allbirds?

4. Joey Zwillinger: The Leader and Person:

• Did Joey take secondaries out during the Allbirds journey?
• How does Joey reflect on his own relationship to money?
• How has Joey dealt with the last 12 months personally? How does he manage the stress effectively?

Jack Altman is the Founder and CEO @ Lattice, the #1 people management platform, last valued at $3BN. Jack is an investor through his founding of Jack Altman Capital where he has invested in WorkOS, NexHealth, Owner.com, Mercury and more.

Auren Hoffman is the Founder and CEO @ Safegraph, the most accurate database of global points of interest, last valued at $550M. Auren is an investor through his founding of Flex Capital where he has invested in Chime, Checkr, Coinbase, Flexport, Vercel and more.

Jason Lemkin is the Founder and CEO @ SaaStr, the world's largest SaaS community. Jason is an investor through his founding of The SaaStr Fund. In the past, Jason has invested in Pipedrive, Algolia, Salesloft, Front, GreenHouse, Owner.com, Gorgias and more.

In Today's Episode on Founder-Led Funds We Discuss:

1. Why have we seen the rise of "Founder-led Funds"?
2. Are founder-led funds more empathetic to the founders they invest in?
3. How do founder-led funds source and pick investments in a way that traditional VC does not?
4. Will we see founder-led Funds truly compete against the Sequoias of the world?
5. How does being an operator make you a better investor?
6. How does investing help you be a better founder and operator?
7. How do you communicate your investing practice and firm to your company and team?
8. What are the biggest excitements and concerns LPs have for Founder-led Funds?
9. Will we see the face of venture changing much more broadly and structurally?
10. How do founder-led funds manage both time and company conflicts?

David Meyer is the SVP Products at Databricks where he drives product strategy and execution. He previously ran Engineering and Product Management at OneLogin, where he grew the company to thousands of customers and market leadership. Before OneLogin, he cofounded UniversityNow, an accredited open university system, running Product and Engineering. Prior to that, David managed a $1 billion portfolio of business intelligence products at SAP and co-led cloud strategy. His first software journey was at Plumtree which went public before being acquired by BEA in 2005.

In Today's Episode with David Meyer We Discuss:

1. Entry into Product:

• How did David make his way into the world of product? Why did he not want to go into it?
• Why does David advise everyone "do not go into product management"?
• What does David know now that he wishes he had known when he entered product?

2. How to be a Great Product Leader:

• Why does David think most leaders suck at leading?
• Why is the most important thing to make your team feel seen? What can leaders do to ensure this?
• Why does David help his team members to find other roles outside of the company?

3. Building the Best Product Team:

• How does David hire for product today? What questions does he ask? What signals does he look for?
• What are David's biggest hiring mistakes? How did they change his approach?
• What are the biggest mistakes founders make when hiring for product?
• Why should you hire people who are not in product today?

4. David Meyer: The Art or Science of Product:

• Is product more art or science? If David were to put a number on it, what would it be?
• Is simple always better when it comes to product?
• Will AI remove the importance and focus on UI?
• Why are the most impressive companies business model innovations not product innovations?

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 in backing from individuals including Peter Thiel and Mark Cuban and it has been reported that the firm now has over $1B in assets under management. Nick has led seed investments in OpenSea, dYdX, SuperRare, Polkadot and Cosmos among others. Prior to 1confirmation, Nick was a Principal @ Runa Capital and before that led business development and marketing at Coinbase in the early days of the company.

In Today's Episode with Nick Tomaino We Discuss:

1. From Cryptokitties to founding the Leading Seed Crypto Firm:

• How did Nick first come into contact with crypto and bitcoin specifically?
• How did getting fired from Coinbase catalyse his move into venture?
• What does Nick know today that he wishes he had known when he started investing?

2. The Landscape Today: Funds and SBF

• Are the current generation of crypto funds too large? Should they give money back to their LPs?
• Will the next generation of crypto funds be smaller? Are any crypto funds able to raise right now?
• Why does crypto Twitter hate crypto VCs? Who are the worst VCs for pump and dump?

3. SBF & FTX: What Actually Happened, Who is to Blame, What Happens from here?

• What is the biggest misconception on SBF and FTX today?
• Who should be held accountable? What else would Nick like to see?
• How should FTX change the way that LPs invest into venture managers?

4. How to Build the Best Crypto Portfolio in Venture:

• How large are the funds? How does Nick determine the right size for a fund?
• How many investments does Nick make per fund? How do loss rates look in crypto?
• What have been Nick's biggest investment hits and losses? How did that impact his mindset?

5. The Future for NFTs and Opensea:

• Why does Nick remain bullish on the future of NFTs?
• How is Nick able to remain optimistic about the future of Opensea given their volumes?
• Where does Nick believe the fair price for Opensea should be today?
• Did Nick sell their Opensea at the $13Bn round?

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 on Seed Rounds We Discuss:

1. The Three Types of Seed Round:

• What are the three different types of seed round today?
• Has seed ever been this competitive?
• Will seed be unimpacted by the macro decline we are seeing?
• Why are growth and multi-stage funds being more active than ever in seed?

2. Too Much Cash Will Kill You!

• Why does Ed believe that too much capital can kill companies at the seed round?
• Why does Ed believe that the best founders are not always optimising for the highest price?
• What are the single biggest negatives of taking a high price at the seed round?
• What advice does Ed have for founders who have large offers from multi-stage funds at seed?

3. Is Growth Dead?

• Why does Ed disagree and suggest that growth is not dead?
• What do multi-stage and growth funds now what to see that they did not before?
• How will the growth market evolve over the next 12-18 months?

4. IPOs, AI and M&A:

• What will cause the IPO windows to crack open again?
• Why does Ed believe that many investing in AI are simply giving money to Nvidia?
• Does Ed agree that 95% of the cash going into AI from venture today will go to zero?
• Will we see more or less M&A in the next 12 months?
• How did Ed evaluate the Loom acquisition by Atlassian?

Ely Lerner is an EIR at Reforge and an advisor for startups transitioning from traction to hypergrowth. Previously he was Head of Consumer Product at Chime, and before that spent an incredible 8 years at Yelp in a number of different roles including Head of Product at Eat24, and Product Leader/GM at Yelp.

In Today's Episode with Ely Lerner We Discuss:

1. Entry into Growth:

• How did Ely make his way from engineering manager to growth leader?
• What are a couple of his single biggest takeaways from his time with Yelp and Chime?
• Why do employees in large companies have to have P&L ownership when innovating within the larger company they are in?

2. Advisors: What, When and How:

• What are the three different types of advisors founders can work with today?
• When is the right time to engage with each of them?
• Should the advisor have had direct experience with the problem you need help with?
• How should these advisors be compensated; what is normal?
• What are 1-2 of the biggest reasons startup advisory roles do not work out?

3. Offense vs Defence: The Tricky Balance:

• What is the difference between offense and defense in product strategy?
• What should the resource allocation be between the two?
• What is the right amount of offensive strategies to have on at the same time?
• How can leaders prevent their defensive teams from feeling like second-class citizens?

4. Ely Lerner: AMA:

• Why does Ely disagree with many and suggest that horizontal products do have a core ICP?
• Should growth teams sit on their own or within functions in the org?
• What are the core reasons teams fail to ship fast?
• What state should your data be in when you bring in your first growth hire?

Matthieu Rouif is the Co-Founder and CEO @ PhotoRoom, one of the fastest-growing YC companies having scaled to an astonishing $50M in ARR in just 3 years. Their capital efficiency is immense having scaled to $20M in ARR on just $2M of invested capital. Prior to founding PhotoRoom, Matthieu founded several start-ups, including an app for ski resorts, HeyCrowd, and Replay, a video editor which was ultimately acquired by GoPro. Whilst at GoPro, Mattheiu led all image editing products.

In Today's Episode with Matthieu Rouif We Discuss:

1. From GoPro to One of YC's Fastest Growing Companies:

• How did Matthieu make the move from GoPro to founding PhotoRoom?
• What are the big mistakes Matthieu made on prior companies that he did differently with PhotoRoom?
• What does Matthieu know now that he wishes he had known when he started PhotoRoom?

2. Scaling to $20M in ARR with $2M of Cash:

• What allowed Matthieu and PhotoRoom to be so capital-efficient in their scaling?
• What are the biggest mistakes founders make when it comes to resource allocation and capital efficiency?
• On reflection, what did Matthieu not spend money on that he wishes they had spent money on?

3. Consumer Subscription + Photo Editing: Is it a Good Business:

• What are the customer acquisition costs by channel for PhotoRoom?
• What are their payback periods on a per-customer basis?
• How can it be a good business when the churn rate annually is 30-40%?
• How does this space play out with Canva, Adobe, Veed, Kapwing? Who wins?

4. The Future of AI:

• Who wins; incumbents or startups?
• What matters more; data size or model size?
• Will UI be more or less important in an AI-first world?
• Why does Matthieu believe that everyone hates command line prompts?
• Will we see $BN revenue companies created with just 10 people?

Harry Stebbings is the Founder of 20VC, building the next great financial institution at the intersection of media and venture capital. 20VC has reached over 125M downloads in 100+ countries and has featured the likes of Doug Leone, Bill Gurley, Marc Benioff, Daniel Ek and more. On the investing side, Harry has raised over $400M and made investments in the likes of Pachama, Linear, TripleDot, Superhuman, AgentSync, Linktree, Sorare and more.

In Today's Episode We Cover:

1. Are LPs Open for Business:

• How has what LPs look for in new manager investments changed?
• What type of funds will be able to raise? Which will not be able to raise?
• What can managers do to significantly increase their chances of raising a new fund?

2. The Seed Investing Landscape: Harder Than Ever

• Why is seed pricing as high as ever?
• Why are multi-stage funds more active in seed than ever? How does this impact seed?
• How will seed change and evolve over the next 6-12 months?

3. Series A + B: The Best Place to be Investing

• Why is Series A the best risk/reward insertion point when investing today?
• How has the competition level at Series A and B changed?
• What do many people not see or know about this stage of the market today?

4. Is Growth Dead: Are Growth Deals Getting Done:

• What two core elements are needed if you want to raise a growth round today?
• How have growth round valuations been impacted over the last 12 months?
• To what extent do founders need to change their expectations on the price of rounds they will be able to get done today?

5. M&A and IPOs: Tough Times Ahead

• Why will we see continued low levels of activity in M&A markets?
• What acquisitions are we seeing take place?
• When will the IPO window crack open?
• Why were Klaviyo, Instacart and Arm not enough to open the windows?

Beezer Clarkson leads Sapphire Partners‘ investments in venture funds domestically and internationally. Beezer has invested in some of the best firms of a generation including USV and Point Nine to name a few. Beezer began her career in financial services over 20 years ago at Morgan Stanley in its global infrastructure group. Prior to joining Sapphire in 2012, Beezer managed the day-to-day operations of the Draper Fisher Jurvetson Global Network, which then had $7 billion under management across 16 venture funds worldwide.

In Today's Episode with Beezer Clarkson We Discuss:

1. LP Landscape: WTF is Going On:

• Are LPs really all closed for business?
• What has changed in what LPs want to see from managers they are looking to invest in?
• What has changed about the size and pace of new commitments for LPs?
• Are all LPs moving away from growth?

2. 2020-2022: Years in Review:

• Are LPs frustrated by managers who reduced deployment timelines to 12-18 months?
• Are LPs frustrated with managers who did not take liquidity when they could have done?
• How does Beezer advise managers on when and how to take liquidity in their best positions?
• Are managers accurately marking their portfolios to their LPs today?
• Why does Beezer believe the incentive mechanism for LPs is broken today in many ways?

3. How To Build a Top Decile Firm:

• Why does Beezer believe if you want to have the best returns, you have to have one company that returns the fund? Can you not do it with multiple half-fund returners?
• Is ownership core to all the best firm's top performance? Is it the size of outcome or the size of ownership that drives the best performance across the board?
• What does data show on how the best funds take significant risk? What are their loss ratios?
• What are the core tradeoffs to Beezer between scaling AUM and providing top decile returns?

4. LP Markets: The Times They are a Changing:

• Does Beezer believe LPs will remain cold on large $1BN+ growth firms?
• Which segments of the market are hot? Which are cold?
• What are the most significant changes we will see in the LP markets moving forward?
• Is today the new normal or are we in a downturn that we will come out of?

Matthew Prince is the co-founder and CEO of Cloudflare, on a mission is to help build a better Internet. Matthew has scaled Cloudflare to over $1BN in revenue, $20BN in market cap, and over 3,200 employees. Today the company runs one of the world's largest networks, which spans more than 200 cities in over 100 countries. Matthew is a World Economic Forum Technology Pioneer, a member of the Council on Foreign Relations, winner of the 2011 Tech Fellow Award, and serves on the Board of Advisors for the Center for Information Technology and Privacy Law.

In Today's Episode with Matthew Prince We Discuss:

1. From Selling Fireworks to Public Company CEO:

• How did Matthew first make money selling fireworks as a kid?
• Does Mathew believe in the trope "you have to love what you do"?
• What does Matthew know now that he wishes he had known when he started Cloudflare?

2. Money, Identity and Happiness:

• Why does Matthew feel many of the most successful founders lose their way when they leave their companies? How does he assess Gates, Bezos and others?
• Does Matthew tie his own identity to Cloudflare and the success of the company?
• How does Matthew evaluate his own relationship to money today? How has it changed over time?
• How does Matthew keep score today on how he is doing? What is success to Matthew?

3. The Three Outcomes for Companies Today:

• What are the three outcomes available to companies today?
• What is the worst and why?
• What are the two biggest mistakes Matthew sees founders make today?
• Why does Matthew know that diverse teams are more successful? What is the proof?
• What is Matthew's single biggest advice to founders when it comes to selecting a co-founder?

4. Focus is BS: You Have to Have Mega Ambition:

• Why does Matthew believe it is BS to have a very specific target customer from the offset?
• What does Matthew believe are the benefits of not having an ICP in the early days?
• What are the biggest pieces of VC advice to founders that Matthew knows to be wrong?

Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade with a portfolio including Lemonade, Melio and HoneyBook, just to name a couple of Aleph’s unicorns.

Adi Levanon is the Founder & Managing Partner @ Selah Ventures, a solo-GP-founded venture fund investing $500k checks into AI-based solutions that enhance financial services, healthcare organizations, fintechs, and SMBs, with a focus on founders in the US and Israelis globally.

In Today's Episode on Israeli Resilience We Discuss:

1. Where are we at today? What is it like on the ground, today?
2. Have the international community reacted as expected? What more can be done?
3. What does it mean to be called up for "reserve"?
4. How are companies dealing with 25% of their teams being called into the armed forces?
5. Are VCs investing still? Does work carry on?
6. Whose reactions are exemplary and we should look to follow?
7. Whose have been woeful and should be called out?
8. What are the single biggest misconceptions of the situation?
9. What can people do to help? What can be done?

Deven Parekh is a Managing Director at Insight Partners, one of the leading investing franchises of the last 25 years. Deven has made more than 90 investments since joining in 2000 including in the likes of Twitter, Alibaba, JD.com, Chargebee and Automattic (WordPress) to name a few.  

Woody Marshall is a General Partner @ TCV, one of the most successful growth funds of the last decade with a portfolio including the likes of Facebook, AirBnB, Spotify, LinkedIn and many more incredible companies.

Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. 

In Today's Episode We Discuss:

1. The Growth Landscape Overview:

• Is growth dead? Are any growth deals getting done?
• How has the price changed for growth deals that are getting done?
• Which type of growth companies will vs will not be able to raise?
• What happens to all of the growth companies with $300-$500M in cash but little revenue?

2. The Great Reset: Valuations Need to Change:

• Why should companies be actively resetting their valuations? What are the benefits?
• What will happen between VCs and LPs when there is no incentive for VCs to reset their portfolio valuations when they need to go out and raise from those same LPs?
• Structure is often part of these valuation resets, is structure to rounds always bad? When is it good? What type of structure is acceptable vs unacceptable?

3. Are the Public Markets Creeping Open:

• Should we take comfort from ARM, Instacart and Klaviyo and assume the public markets are going to open again? If not, what will cause them to open?
• How should we analyze the performance of the IPOs above? Many have been negative, are they right to suggest this is not the response we wanted?
• Why does Woody believe, like Instacart taking a 75% discount to their last round, we should have more and more companies go public at discounts to their last private round?

4. Late Stage Growth is Dead and Revenue Multiples:

• Why is late-stage growth dead? How long do we think this will last?
• How should we assess revenue multiples today? New normal? Same as always? How will revenue multiples look in 12 months from now?
• How should we analyse the large late stage growth rounds for hyped AI companies? What happens there?

Scott Farquhar is the Co-Founder & Co-CEO @ Atlassian. Scott co-founded the company with his university friend, Mike Cannon-Brookes, in 2002 from Australia. Over an incredible 20-year journey they have grown to a market cap of $50BN today, over 11,000 staff globally and serving over 260,000 customers. Scott is also a co-founder of Skip Capital, a private investment fund with a portfolio including Figma, Snyk, Canva and more.

In Today's Episode with Scott Farquhar We Discuss:

1. The 20-Year Journey to $50BN Market Cap:

• How did Scott first make his way into the world of tech and come to co-found Atlassian?
• What does Scott know now that he wishes he had known at the beginning?
• From 20 years with Mike, what is Scott's biggest advice on choosing your co-founder?

2. The Fundraising Masterclass with Atlassian:

• An emergency phone call, a honeymoon cut short; how did the first funding round for Atlassian come to be? Where was the business revenue-wise at the time?
• Why did Scott not like the traditional fundraising process? What did he do to add game theory and ensure that they got the best deal as a company?
• Why did Scott choose Accel with their offer? How did Peter Fenton lose a $3BN deal with Atlassian?

3. Lessons Scaling Atlassian to $4BN in Revenue:

• What does Scott believe are the 4 core roles of the CEO? Is resource allocation the most important?
• What are the single biggest acts of commission and omission that Scott regrets?
• What are the biggest lessons Scott has from shutting down Stride, their Slack competitor?

4. Scott: The Father, Husband and Philanthropist:

• What does great fatherhood mean to Scott today?
• What is the secret to a truly successful marriage?
• How does Scott assess his relationship to money today? How has it changed with time?
• How does Scott think about bringing children up in a world of affluence and abundance?

Fun Fact: Every single 20VC episode is recorded with Riverside.FM. It is the one product that I could not live without. Try it today here (https://creators.riverside.fm/20VC) and use the code 20VC for 15% off.