20VC: Floodgate's Mike Maples on What Makes Category Kings, What Most Venture Funds Do Wrong When Hiring & 'The Dance Of Product Market Fit'

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?

13 Helmi 202345min

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?

10 Helmi 202344min

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?

8 Helmi 202344min

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

6 Helmi 202354min

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70-person product and design org. Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe's first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter. David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos. Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay. Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products. Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and one of the most popular newsletters on Substack. For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015. Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe's Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012. In Today's Episode on How to Hire a Product Manager, We Discuss: 1.) When to Hire Your First PM: What are the core signs that the founder must delegate and hire their first PM? What are the first things that are breaking when you do not have one but need one? How does the timing of the first PM differ when comparing B2B vs B2C? 2.) What is the Right Profile: What should founders look for in this first PM hire? What traits make the best? What are the biggest red flags in the personalities and styles of potential candidates? Should they have experience in the product domain they are entering? What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume? 3.) The Hiring Process: How To Hire a Product Manager How do we structure and run the hiring process for this person? What tests can we do to understand if they have the skill set we need for the role? How do we structure a hiring panel to make this process more effective? What are the biggest mistakes founders make in the hiring process for PMs?

3 Helmi 202354min

Alex Bouaziz is the Co-Founder and CEO @ Deel, the all-in-one platform made to simplify all things HR, built for global teams near and far. In the last year alone, Alex has scaled Deel from $57M in ARR to $295M, EBITDA positive since Sept 2022, 85%+ gross margins, and over $5BN paid out to 250,000 people. Alex has raised over $679M with Deel, pricing the company at the last round at $12.1BN. Investors in the company include a16z, Spark Capital, Coatue, and many more. In Today's Episode with Alex Bouaziz We Discuss: 1.) From Student in London to Decacorn Founder: How Alex made his way into the world of startups and how he came up with the idea for Deel? Did Alex always know he would be successful when he was growing up? What does Alex know now that he wishes he had known when he was starting? 2.) The Importance of Execution: How important does Alex think speed of execution is for startups? What can startups do to deliberately increase their speed of execution? How does Alex think about the dilemma of losing quality with speed? What does Alex think you do need to go slow on to ensure it is perfect? How does Alex think about focus and prioritisation today with Deel? 3.) Scaling to $295M in ARR in 3 Years: When did Alex know he had true product-market fit with Deel? How did Alex use a 50-person Whatsapp group to both determine product market fit and to navigate product direction for the company? What was the key to Deel's blitz scaling strategy? What worked? What did not work? How did Alex hire 2,000 people in such a short space of time? What broke first in the organisation? How could they have prevented it? 4.) Secondaries, Angel Investing and Wealth Management: How much did Alex take out in secondaries in the last round of funding? How did Alex determine how much cash to allocate to angel investing? Why does Alex believe most founders make poor angel investments when they have cash? What have been Alex's biggest lessons from investing? How has it changed how he operates? Why should all founders be super transparent in investor updates?

1 Helmi 202344min

Hunter Walk and Satya Patel are Co-Founders and Partners @ Homebrew, one of the leading seed funds of the last decade. Following 10 years of stellar returns with investments in the likes of Chime, Plaid, Gusto and many others, they decided to not accept any further LP capital and to only invest their own money moving forward through Homebrew Forever. In Today's Discussion on Homebrew We Breakdown: 1. ) The Foundings of a Great Partnership: What was the moment when Hunter and Satya decided they were going to go out and raise their first fund with Homebrew I? What are the core principles that all founding partners need to align on before they start a firm together? What questions should they ask of each other? Why does being independently wealthy coming into a partnership make the partnership easier and more efficient to operate? What changes when the partners have money already? 2.) What Changes When Moving From LP Dollars to Personal Capital: Why did Hunter and Satya decide to not raise any further capital from external LPs? Asset allocation-wise, how did they determine how much is the right amount to set aside for the first 2 years of investing? How many investments do they want to make with that cash? How does investing their personal capital change their deployment pace and cadence? How does it change their approach to reserves management and follow-on financing? How does it change their approach to pricing? How price sensitive are they today? 3.) Analyzing the Seed Landscape Today: Why do Hunter and Satya not think that a $100M seed fund is enough to properly execute a world-class seed strategy today? Who is their competition with the new strategy? How does it change their relationship with large multi-stage funds? How does it change their relationship with seed funds? Do they agree that the last generation of sub $20M micro-funds will not raise another fund in this cycle? How did their entrance impact the seed landscape over the last few years? Why are LPs also to blame for many of the original seed managers raising larger and larger funds? 4.) Companies: Money and People are The Problem: Why has too much money been such a problem for many Homebrew portfolio companies over the last few years? How has too much money changed their execution plans? What happens to the "living dead" companies with many years of runway but no product market fit? Who does this market cater to well? Who will thrive in this market? What have people forgotten about both startups and venture in the last 2 years that we have to remember? Why is this generation so entitled and expectant? Why are startups not a get-rich-quick scheme?

30 Tammi 20231h 1min

Cliff Obrecht is the Co-Founder & COO @ Canva, the free-to-use online graphic design tool that makes it easy for anyone to design anything from presentations to videos and social media. Cliff and Mel have scaled Canva to over 60 million monthly users, 2,000 employees, and 500,000 teams from companies like Intel and Zoom using Canva. During this incredible growth journey, they have raised over $580M with their last round valuing the company at over $40BN. In Today's Episode with Cliff Obrecht 1.) From Teacher to Billionaire Tech Founder: How did Keith make his way into the world of tech with his founding of FusionBooks? What did the process with FusionBooks teach him about how to run Canva? How did the early fundraising days for Canva go? Why does Cliff think they got over 100 no's? What are Cliff's biggest pieces of advice for founders today, not in Silicon Valley, looking to raise from Silicon Valley VCs? 2.) Scaling to $40BN: The Biggest Lessons: What does Cliff mean when he says the secret to successful hiring is looking for "distance traveled"? How does he determine this in the interview process? What have been some of the single biggest lessons in what it takes to acquire the best talent? What are some of the biggest mistakes Cliff has made in talent acquisition? How has his process changed as a result? What do Canva do to get the best operators as advisors in the company? How do they compensate these advisors? What does Cliff advise founders on how to do the same? 3.) The Art of Deal-Making: How does Cliff think through what makes a "good deal"? How does he approach negotiation? What are the biggest mistakes founders make when negotiating and doing deals? What have been Cliff's biggest lessons on successful investor relations over the years? How does Cliff and Canva approach acquisitions? What do they look for? What is their process? Why do most tech companies approach acquisitions the wrong way? 4.) Cliff Obrecht: Money, Fatherhood and Marriage: How does Cliff analyze his relationship to money today? How much money is enough? How has his relationship to money changed over time? Why have Cliff and Mel given away over $10BN to their foundation? Why is philanthropy so hard to do effectively? Why would Cliff hate for his children to be brought up in excess wealth? What does "great fatherhood" mean to Cliff? What are the most challenging aspects of parenting? What are the secrets to a happy marriage? How does co-founding a company with your other half work well? How does it work poorly?

27 Tammi 202350min