Tobi Lütke is the CEO and Co-Founder of Shopify, the powerhouse company allowing anyone to start and grow their e-commerce business. Over an incredible 18 years, Tobi has scaled Shopify to 10% of total US e-commerce, millions of merchants in over 170 countries, and a market cap today of over $60BN. Huge thanks to Harley Finkelstein for making this happen.

In Today's Episode with Tobi Lütke We Discuss:

1. From a Small German Town to One of the World's Most Powerful CEOs:

• What did Tobi want to be when he was growing up?
• Who did Tobi learn most from in his younger years? How does Tobi think about the importance of mentorship in learning?
• What does Tobi know now that he wishes he had known when he started Shopify?

2. You Can Learn More from World of Warcraft Than You Can Companies:

• Why does Tobi believe you can learn more from World of Warcraft than you can from studying companies?
• Why does Tobi believe that humans are terrible at company building? What are the most obvious ways we can improve the quality of the companies we build?
• Why does Tobi believe that in-person is far superior to remote working? What are the nuances?

3. The Best Companies Operate with Many Constraints:

• Why does Tobi believe in all cases, constraints produce creativity?
• What is the difference between an enforced constraint and an artificial constraint?
• How can leaders create and enforce artificial constraints when they are not real?
• How do the best leaders use constraints to ensure their companies move faster and faster?

4. Inside the Mind of Tobi Lütke: Decision-Making & Prioritisation:

• How does Tobi reflect on his own decision-making process? How has it changed?
• Why does Tobi believe that sunk cost fallacy is BS and only leads to your outsourcing approval to someone else?
• Why does Tobi hate "black boxes"? How does he remove them from the org entirely?
• How does Tobi decide what to learn? What is his learning process once he has made this decision?
• How does Tobi decide what to prioritise in terms of strategic initiatives for Shopify?

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

In Today's Episode with Jackie Reses We Discuss:

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

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

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

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

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

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

4. The Next Wave of Fintech:

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

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

In Today's Episode with Jag Duggal We Discuss:

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

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

2. Product: The Playbook, Art vs Science:

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

3. Building the Bench: Hiring the Best Team:

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

4. Go Time: Build, Manage and Execute:

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

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

In Today's Episode with Dara Khosrowshahi We Discuss:

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

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

2. Dara Khosrowshahi: The Foundations of Great Leadership:

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

3. Investments and Acquisitions: The Scorecard:

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

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

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

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

In Today's Episode with Mike Maples We Discuss

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

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

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

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

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

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

4.) Lessons from SVB: The Wider World:

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

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

In Today's Episode with Frank Fillman We Discuss:

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

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

2.) Build and Execute the Sales Playbook:

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

3.) Enterprise Deal Dynamics 101:

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

4.) Building the Bench:

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

5.) Setting Quota and Deal Reviews:

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

Items Mentioned in Today's Episode:

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

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

In Today's Episode with Bill Ackman We Discuss:

1.) From HBS to Starting Your First Fund:

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

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

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

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

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

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

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

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

In Today's Episode with Ophelia Brown We Discuss:

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

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

2.) Venture Capital: The Market:

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

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

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

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

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

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

In Today's Episode with Adam Grenier We Discuss:

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

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

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

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

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

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

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

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

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

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

In Today's Episode on SVB We Discuss:

What Happened?

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

What Now?

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

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

In Today's Episode with Amjad Masad We Discuss:

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

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

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

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

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

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

4.) Building the Replit Army:

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

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

In Today's Episode with Glen Coates We Discuss:

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

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

2. The Art of Product and Product Management:

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

3. The Art of Product Marketing:

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

4. Shopify and The Future of Shopify:

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

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

In Today's Episode with Alex Schultz We Discuss:

1. From Paper Planes to CMO of Facebook:

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

2. The Secret to Scaling to 1 Billion Users:

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

3. Crucible Moments in Facebook History:

Facebook Messenger Split:

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

Rebrand to Meta:

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

Reels vs TikTok vs SNAP:

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

4. Alex Schultz: The Person and Leader:

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

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

In Todays Episode with Hunter Somerville We Discuss:

1. Three Types of Secondaries:

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

2. LPs Today and Moving Forward Investing in Funds:

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

3. Liquidity: When Does the Cash Hit:

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

4. AMA with One of the Largest Secondary Buyers:

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

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

In Today's Episode with Jamie Siminoff We Discuss:

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

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

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

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

3.) Jamie Siminoff: The Leader:

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

4.) Selling for $1BN to Amazon:

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

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, Flatiron Health, Stripe, Warby Parker, Harry’s, Oscar, Flexport, Classpass, Vine, GroupMe, Airtable and more. David is also the Chairman of GoodDog, a marketplace to find pets online.

In Today's Episode with David Tisch We Discuss:

1.) From Techstars To Founding BoxGroup:

• How did David start his own firm in the form of Box having started at Techstars?
• What advice from Brad Feld does David always remember and hold close?
• What does David know now that he wishes he had known when started investing?

2.) The Debate: The Math Does Not Work: Portfolio Construction:

• Ownership Does not Matter: How does David justify writing $100K checks from a $127.5M early-stage fund? Even if it is a home run, it does not make a difference to the fund?
• Level of Diversification: If David is writing small checks like this, with his fund size he will have hundreds of companies, what does David believe is the right level of diversification?
• Reserves management: How does David think about the ratio of initial to reserves when deploying the funds today? How does reserves management change in a recession?
• How does David prevent other VCs from using this to try and push him down to always writing a $100K check?
• Why does David believe that the size of check he is able to invest is the VC's problem and not the founders?
• Price Sensitivity: How does David assess his own relationship to price today? Why does he believe that company valuation is not something that the investor controls?

3.) Advice to Founders Raising Rounds:

• What does David believe is the #1 role of the CEO?
• What are the three most important variables for founders to focus on when raising their round?
• How should founders analyze the tradeoff between the brand of the VC and the size of the round?
• Does signaling really make a difference when a large fund invests at seed?
• How did multi-stage funds change the seed landscape forever with a new product?
• Who does David believe are the tourists in early-stage venture? Will they leave in the recession?

4.) David Tisch: AMA:

• Why does David believe that consumer social is not fun anymore?
• Who when they send him a deal does David take it most seriously?
• How does David want to ensure that bad VC behaviour is exposed?
• What would David most like to change about the venture landscape today?

Joey Levin is the CEO of IAC where he has overseen the constant evolution of the company, including the initial IPO and subsequent spin-off of Match Group, the spin-off of Vimeo, and the acquisitions of Angie’s List and Care.com. If that was not enough, in October 2022, Joey was also appointed as CEO of Angi Inc. In addition to this, Joey also serves on the boards of IAC, Turo, and MGM Resorts International.

In Today's Discussion with Joey Levin We Discuss:

1.) The Makings of a Great Leader:

• When Joey was younger, what did he want to be when he grew up?
• What is Joey's biggest advice to people coming out of college/university at this time?
• What 1-2 things does Joey credit his internal and fast rise in IAC to?

2) Value Investing is BS & The Markets Today:

• Why does Joey believe the idea of "value investing" is BS?
• What 1-2 behavior traits of investors in the last few years were most dangerous?
• Why does Joey believe that the current market is reasonable and now is the new normal?
• How does Joey keep internal morale high when people have become accustomed to high stock prices?
• Does Joey believe in the statement, "be greedy when others are fearful and fearful when others are greedy"?

3.) Simplification is the Secret to Margin & Messaging 101:

• Why does Joey believe simplification is the core of high margins?
• How can startups and scale-ups identify where to simplify first? What are the subsequent steps?
• Why does Joey believe that the best values should make you feel uncomfortable?
• What is a lesson from Joey's father on what makes truly great messaging?

4.) Parenting, Money and Marriage:

• How does Joey reflect on his own relationship to money today?
• What are 1-2 lessons taught by his mother on how to approach money and wealth?
• What does Joey believe is the secret to truly happy marriages?
• What are Joey's biggest lessons on what it takes to be an effective and good father?

Kevin Systrom and Mike Krieger are the co-founders of Instagram. Since its release in 2010, Instagram has become of the most significant products in modern society shaping the way millions of people engage with the world around them. In January this year, Kevin and Mike announced their return to the founding arena with the launch of Artifact, a personalized news feed driven by artificial intelligence.

In Today's Show with Kevin Systrom and Mike Krieger We Discuss:

1.) The Perfect Partnership:

• Question from Josh Kushner @ Thrive: What makes Kevin and Mike such a great partnership?
• What was the last disagreement they had? How was it resolved?
• They built Instagram in person, in an office. They are building Artifact remotely, what has changed in the way they operate when comparing remote to in-person?

2.) Why Social Networks are Broken & The Next Frontier:

• Why does Kevin believe social networks today are broken and should be less social?
• What fundamental premise are social networks built on that Kevin believes is wrong?
• How will AI and machine learning be central in the next wave of social?
• How do Kevin and Mike evaluate TikTok and the next wave of content discovery?

3.) Welcome Artifact: The Comeback:

• Why does Kevin believe they chose the worst idea for their new company? Why is it?
• Were they nervous about founding Artifact and expectations being so high given Instagram?
• Why does Kevin argue that Artifact is not actually a "news app"?
• What does Kevin believe is the biggest lesson Apple taught us about messaging?

4.) Family, Money, San Francisco:

• Why does Kevin believe that SF will return as the centre of tech once again?
• Why does Kevin believe that many millennials in the workforce today are entitled and soft?
• How has becoming a father changed the way Kevin and Mike operate and execute?
• How do Kevin and Mike assess their relationship with money today? How has it changed?

5.) Hiring, Investing, Managing:

• What are some of Kevin and Mike's biggest lessons when it comes to hiring?
• What are the single biggest hiring mistakes they have made?
• Is it wrong to not hire someone because they are really really boring?
• What are the biggest lessons for Kevin and Mike from their angel investing?

Zach Lawryk is Head of Solutions Consulting @ Rippling, what is solutions consulting? They are the product expert in the solution that ties a business value to help support the sales rep in the execution of their quota. And there is no one better than Zach, prior to leading the solutions consulting team at Rippling, Zach was VP of Solutions Consulting at Slack where he scaled the SE team from 10 to 200. Before Slack, Zach was Head of Solutions Engineering @ Optimizely and before that was Director of Sales Engineering at Box.

In Today's Episode with Zach Lawryk We Discuss:

1. ) WTF is Solutions Engineering:

• What is Solutions engineering and why is it important?
• How does a software developer turned lawyer become one of the OGs of Solutions Engineering?
• What is the single biggest piece of advice Zach gives to graduates entering the workforce today?

2.) When and Who: Building the Foundations:

• When is the right time to hire your first solutions engineer?
• Should this be a senior hire or a more junior hire? What experience is ideal?
• Would Zach rather have someone who has sold to the same customer segment or sold to the same deal size? What are the challenges with each?

3.) Making the First Hire: The Process:

• What is the right hiring process for solutions engineers?
• Which members of your existing team should be involved in the process?
• What are some of Zach's favourite questions on the candidates past to determine quality?
• What are the best case studies and tests to give potential hires to test their aptitude?
• What are the biggest red flags in the hiring process for solutions engineers?

4.) Integrating into the Team: Making it Work:

• What is the optimal onboarding process for solutions engineers?
• Why does Zach think it is important they spend time with customer success in their first month?
• What is the right way to measure the effectiveness of SE's?
• How should the entrance of SE's impact the close rate and comp structure for AE's?
• How can sales leaders prevent division and friction between AEs and SEs?

Aloe Blacc is a GRAMMY nominee and the voice behind such hits as Wake Me Up, The Man, SOS, I Need A Dollar, and many more. Aloe has toured the world, won countless awards but his latest album, All Love Everything, is the singer-songwriter’s first collection of material written as a father. “Becoming a father made me want to share those experiences in music,” he says, admitting it’s a challenge to translate such a powerful thing into lyrics and melody. If that was not enough, Aloe is also an entrepreneur with the founding of his new company, something we discuss in the show today.

In Today's Discussion with Aloe Blacc:

1.) Entry into Music and Running From Fame:

• How Aloe first fell in love with music and made his foray into the world of music from Ernst & Young?
• Why does Aloe believe he is running from fame? What does it bring that he does not like?
• What does Aloe believe he is running towards? How has this changed?

2.) The Art of Storytelling:

• How does Aloe think about what it takes to be truly great at storytelling?
• What is the difference between a great vs an average story?
• How has his style of storytelling changed over time?
• What are the biggest mistakes that people make in storytelling?

3.) The Songwriting Process 101:

• What is Aloe's process for writing new songs?
• How does he take an idea and expand it, test it and execute against it?
• How did "Wake Me Up" with Avicci come about? What was the creation process there?
• What was it like working with Avicci? What did Aloe learn from him about being liked?

4.) Marriage, Fatherhood, and Global Stardom:

• What does Aloe believe is the key to truly successful marriages?
• How does Aloe retain a sense of romance with intense work pressures?
• How has becoming a father changed the way in which Aloe thinks and operates?
• What is Aloe's love language? How has doing this with his wife changed their relationship?

Mike Duboe is a Partner @ Greylock where he sits on the board of Builder, Inventa, Novi, Pepper, Postscript. Prior to entering the world of venture, Mike was the first in-house growth hire at Stitch Fix, where he built and led the Growth organization helping take the company through to their IPO. Before Stitchfix, Mike was the first growth hire at Tilt, where he built and oversaw multiple teams, including analytics, marketing, community, and growth product. He also served on YC’s growth advisory council and was a growth lecturer at Reforge.

In Today's Episode with Mike Duboe We Discuss:

1.) Entry into the World of Growth:

• How Mike made his way from consulting at Bain to leading the growth team for Stitchfix?
• What did Mike believe about growth 5 years ago that he no longer believes?
• What does Mike know now that he wishes he had known when he entered the world of growth?

2.) When and Who To Hire:

• How does Mike define the term "growth team"? What is their core role and responsibility?
• Should the first growth hire be a senior growth lead or a more junior analytical lead?
• What data foundations should founders have in place prior to their growth hire joining?
• What are the most common ways founders fail to prepare for their first growth hires joining?
• When does Mike believe is the right and crucial time for growth hires to be made?
• Should these growth hires join existing teams or be put in standalone "growth teams"?

3.) The Hiring Process: How to Detect and Win the Best:

• How should founders structure the interview process for their first growth hires?
• What are the best questions to ask to reveal the quality of a potential growth hire?
• What are the right case studies and tests to do to assertain their quality?
• What are the different levels of comp package for different growth execs?
• What are the single biggest mistakes founders make in the hiring process?

4.) Mastering Paid Marketing: Lessons from Stitchfix:

• Why is CAC/LTV a BS metric? What should be used instead?
• When is the right time to start really engaging with paid marketing?
• How should marketing and growth teams determine budget on a per channel basis?
• How much is the right mix between paid vs organic?
• What are Mike's biggest lessons from making paid work so well at Stitchfix?
• What are the single biggest mistakes Mike sees founders make today with paid marketing?

Tom Loverro is a Partner @ IVP where he has led or was actively involved in investments in Amplitude, Coinbase, Hashicorp and Datadog to name a few. As a result of his investing success, Tom was named to Forbes Midas List in 2021. Prior to joining IVP, Tom was a Principal at RRE Ventures.

In Today's Episode with Tom Loverro We Discuss:

1.) The Entry into Venture:

• How did Tom make his way into venture first with RRE? How did the role with IVP come about?
• Does Tom believe we will see many venture investors move firms with much of their existing expected carry cut in half with the changing landscape?
• What is Tom's biggest advice to someone looking to make their way into the venture world?

2.) The Calm Before the Storm:

• Why does Tom believe now is the calm before the storm?
• Why does Tom urge founders to go out and raise now before the storm hits?
• Is Tom already seeing pricing coming down for both early and late-stage companies?

3.) When The Storm Hits:

• When does Tom believe the storm will hit?
• Why does Tom believe when it does hit, it will be worse than The Great Financial Crisis?
• How will VCs respond when the storm hits? How will it impact their investing cadence?
• How will LPs respond when the storm hits? Will they cut back their manager commitments?
• Does Tom have hope that their will be a new class of LPs in this new economic cycle?

4.) The Rounds That Happen When The Storm Hits:

• Does Tom believe we will see a wave of down rounds when the storm hits? Why are they less common than people think?
• In the eye of the storm, will we see further layoffs? Will we see firesales? Will we see a tidal wave of shutdowns?
• Will large multi-stage funds with huge amounts of dry powder change their deployment pace?

The Survival Guide for the Storm:

1.) Raise Now:

• Why does Tom believe that startups should raise now, not later? What amount of runway should they raise for in this environment?

2.) Cut, Cut and Cut Some More:

• What amount of runway should startups be cutting to get to?
• How will this impact marketing spend? Why are your marketing dollars more powerful now than ever before?

3.) Focus on Survival Not Valuation:

• What does Tom mean by this? How can founders gain leverage with VCs when raising today?
• How can founders instil a sense of urgency in their raise with investors?

4.) Bring on Operators with Experience:

• Why would operators with experience join a struggling startup?
• Will operators with experience not have a flight to safety and stay at their well-paid FANNG role?
• Does this potential operator not shorten runway even further as they are often expensive?

5.) Unit Economics over Growth:

• How can founders show investors a superior profile of unit economics moving forward?
• Do investors not want both unit econ and growth today?

6.) Play Your Cards Right and Then Go on Offense:

• How does Tom advise founders on the right time to go on offense?

7.) Be Decisive, Half Measures Rarely Succeed:

• How does Tom define a half-measure? What is so wrong with half-measures?

Steve Pagliuca is a Senior Advisor at Bain Capital, the firm he joined in 1982 and as a Managing Director of Bain Capital, he has helped build the firm into one of the world’s leading investment companies with over $160 billion in assets under management. Steve is also a Managing Partner and Co-Owner of the World Championship Boston Celtics Basketball franchise. Steve is also co-owner and co-chairman of the Serie A professional football club, Atalanta Bergamasca Calcio. If that was not enough, Steve currently, serves on the Board of Directors of Burger King, Gartner Group, HCA, Warner Chilcott, and FCI. Huge thanks to Moshe @ Shrug Capital for making the intro.

In Today's Episode with Steve Pagliuca We Discuss:

1.) From Duffel Bags at Duke to Buying Sports Teams:

• How Steve went from having a single duffel bag arriving at Duke University to entering the world of private equity with the founding of Bain's PE funds?
• Did Steve always know he would be successful? What does Steve think about the importance between luck and timing?
• How did Steve's mother impact how he approaches parenting and self-belief with his children?

2.) Buying Sports Teams: Not So Different to Companies:

• When buying and running a sports team, what is the same, and what is different from buying and running a company?
• What is Steve's biggest advice to new owners of sports teams?
• What are the single biggest mistakes sports team owners make when they buy a team?
• What happened with the Chelsea bid? Why did Steve lose? How did debt change the deal?

3.) The Future of Sports Ownership:

• Why does Steve believe we have seen a massive rise in American and private equity buyers of both global sports teams but also European sports teams?
• How has "new media" changed the inherent value that can be placed on a team? Why does it change the value? Which forms of "new media" are most important?
• How much further can the value of these sports teams increase?
• Does this massive increase in the price and assets of certain clubs not lead to a massive inequality in sports? What can be done to prevent this imbalance?

4.) Steve Pagliuca: The Person and Capital Allocator:

• What is the single best investment advice Steve has ever received?
• How does Steve think about his relationship to wealth today? How has it changed over time?
• What does it take to have an amazing marriage and be at the top of your profession?
• What were 1-2 elements that made Bain able to scale to the proportions of AUM that they have done? What would he have done differently?

Ariel Cohen is the Co-Founder and CEO @ Navan (formerly TripActions), the #1 travel management super-app used by over 8,000 companies. Ariel has raised over $2BN for Navan from some of the best including a16z, Zeev Ventures, Lightspeed, Greenoaks, and Elad Gil. Prior to TripActions, Ariel co-founded streamOnce, a business multimedia integration platform that was successfully acquired by Jive Software, where Ariel had previously served in a senior position following his time at Hewlett-Packard.

In Today's Episode with Ariel Cohen We Discuss:

1.) Why Education is Outdated and Wisdom to People Entering the Working World:

• Why did Ariel not really attend many classes when he was a student?
• What would be his biggest advice to young people leaving school today? Where would he focus?
• Why does Ariel believe that traditional education is more outdated now than ever before?

2.) Why SAP and Salesforce Will Die:

• Why does Ariel believe that SAP and Salesforce have not innovated for a decade?
• Why does Ariel believe that Slack is a disaster inside of Salesforce?
• What are the single biggest advantages that startups have over these large incumbents?
• What can startups do to retain innovation and speed as they scale into becoming an incumbent?
• Why are the best founders willing to kill their own projects?

3.) Growing a Business 3x and Raising at a $9.2BN Valuation in COVID:

• How did Ariel grow the business 3x with all travel being banned?
• What were the tactics to blitz scaling during COVID?
• How did Ariel approach his investors for a new round in the middle of COVID? How did he get such a high price in the midst of a global pandemic?
• What is the bull case for how Navan can be a $40BN company?

4.) Margins Matter: Gaining Leverage Through Additional Margin:

• With Navan's 80% margin, they have 30% higher margins than other competitors, how do they have such high margins?
• With the additional 30%, how does Ariel plan to scale Navan's reach and use the margin to do so?
• How does OpenAI play a role in helping Navan increase its margin even further?

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. Today, Orlando directs the firm’s strategy and investment decisions. Orlando has overseen over 420 software acquisitions conducted by the firm, representing more than $235 billion in transaction value. Forbes named him "Wall Street’s best dealmaker" in 2019, and he was dubbed "Private equity’s king of SaaS" by the Financial Times in 2021.

In Today's Episode with Orlando Bravo We Discuss:

1.) From Puerto Rico Roots to Wall Street's Best Dealmaker:

• How did Orlando come to co-found Thoma Bravo? What was that a-ha moment for him?
• Orlando mentioned 2 mentors that shaped how he thinks, who were they? What are his single biggest lessons from those mentors?
• What does Orlando know now that he wishes he had known when he started his career?
• Why does Orlando disagree with setting timelines in life? Why does it not help?

2.) The Secret to Success in Value Investing:

• What is good value investing today? What is it not?
• What three things does Orlando look for when doing a deal and acquiring a company?
• Why is every company in the world worth its future cash flows?
• How important is price today? How does Orlando reflect on his own price sensitivity?
• Many suggest Coupa and Anaplan were extremely expensive. How does Orlando respond and defend the prices he paid for companies in 2020-2022?

3.) WTF is Happening In Markets Today:

• How does Orlando reflect on where the market is today?
• Is this the new normal? How does Orlando expect the market to change over the next 12 months?
• Why does Orlando believe that the best companies win in the worst times?
• Is this the result of quantitative easing on behalf of central banks? Who is to blame?
• How does Orlando balance the mindset of his team between risk on and taking advantage of lower prices in market but also not catching a falling knife?

4.) Orlando Bravo: The Leader, Father and Husband:

• What is Orlando's biggest fear in investing? How has this changed over time?
• How does Orlando reflect on his own relationship to money today? How has that changed?
• What are Orlando's biggest parenting lessons from his mother?
• Why does Orlando believe that for most people, their late twenties are their toughest?
• How does Orlando instill the same drive and ambition in his children that he had, despite very different financial profiles growing up?
• How does Orlando maintain being at the top of his game in his profession but also being a great husband? What is the secret to a happy marriage?

Items Mentioned in Today's Episode:

Orlando's Fave Book: The Power of Now: A Guide to Spiritual Enlightenment