Steven Galanis is the Founder & CEO @ Cameo, the startup that allows you to book personalised shoutouts from your favourite people. To date, Steven has raised over $65m in VC funding for Cameo from some of the very best in the business including Bedrock, Nicole Quinn @ Lightspeed, Kleiner Perkins and Spark Capital, just to name a few. Prior to founding cameo, Steven was a Senior AE @ LinkedIn and before that was an options trader in Chicago. With their immense success, they have been featured in all major publications including The Ellen DeGeneres Show. Cameo has also been voted as "The Best Place To Work In Chicago" by GlassDoor.
In Today’s Episode You Will Learn:
1.) How Steven made his way from AE @ LinkedIn to revolutionising what an autograph means today with his founding of Cameo?
2.) What does Steven believe is the No 1 reason that startup founders fail with their startup today? Why does Steven believe that you have to give up your job to pursue your startup, even in the earliest of days? What advice does Steven give to founders and young graduates who approach him for advice in the earliest of days?
3.) As the company scales, how does Steven think about and approach role allocation internally? How does he prioritise hiring for them? How does he think about internal upscaling? How has he dealt with letting go of responsibilities and delegating to the team? What are the core challenges here? What does he advise founders facing this?
4.) Steven has said before, "don't let good get in the way of great", what did he mean by this? How does he determine between good enough and a stretch too far? How does Steven think about the statement of hiring for 6 months ahead of where you are? What have been his biggest lessons from scaling internationally so fast?
5.) How does Steven think about and approach investor selection? What can founders really do to leverage their investor base and get the most value from them? How does Steven think about the incredibly high CACs of the core channels today? What must founders in the world of consumer do to acquire customers more efficiently?
Items Mentioned In Today’s Show:
Steven’s Fave Book: Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies
As always you can follow Harry, Steven and The Twenty Minute VC on Twitter here!
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Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston where his research coverage included such companies as Dell, Compaq, and Microsoft, and he was the lead analyst on the Amazon IPO.
In Today’s Episode You Will Learn:
1.) How did Bill make his way into the world of VC from Credit Suisse and come to be GP at one of the world's leading funds in the form of Benchmark? What were Bill's biggest takeaways from seeing the boom and bust of the dot com? How did that impact Bill's investment mentality today?
2.) Why does Bill believe that one of the biggest challenges today is the abundance of capital? Subsequently, does Bill agree with Peter Fenton statement, "never turn down a deal based on the valuation it is a mental trap"? How does Bill assess his own price sensitivity? What was his learning here in meeting Larry and Serge early on with Google?
3.) How does Bill think about and approach market sizing today? How important is it to him when analysing an investment? Where does Bill believe a lot of managers make mistakes when assessing market sizing today? What was his big lesson here with Uber? How does Bill think about and evaluate market creation and market expansion plays?
4.) Bill has spent over 3,000 hours on some of the most famed boards of the last decade, how has Bill seen his style of board membership change over the last 10 years? What advice would you give to someone who has just joined their first board? How does Bill think about time allocation across the portfolio? What is the right ratio?
5.) How does Bill and Benchmark approach the element of partner selection today? What are the 5 core things that Bill looks for when adding to the partnership? What have Benchmark done that have allowed them to be so successful in generational transition? Why is an equal partnership so transformative when it comes to generational transition?
Items Mentioned In Today’s Show:
Bill’s Fave Book: Complexity: The Emerging Science at the Edge of Order and Chaos
Bill’s Most Recent Investment: Good Eggs
As always you can follow Harry, The Twenty Minute VC and Bill on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Justin Kan is the Founder and CEO @ Atrium, the startup providing a full-service corporate law firm that uses modern technology to give startups a legal experience that is fast, transparent, and price-predictable. To date, Justin has raised over $75m in funding from some of the best in the business including Founders Fund, a16z, First Round, General Catalyst, Thrive, Initialized and more. Prior to founding Atrium, Justin was a Partner @ Y Combinator, the globally renowned accelerator and the birthplace of some of today's largest startups. Before that Justin was the Co-Founder @ Twitch, the world’s leading video platform and community for gamers which was acquired by Amazon for $970m. If that was not enough, Justin is also a prolific angel investor with investments in the likes of Cruise Automation, Rippling, Zenefits, Triplebyte and more.
In Today’s Episode You Will Learn:
1.) How Justin made his way into the world of startups and YC? How that led to the founding of Justin.TV, later Twitch? What was that a-ha moment for Atrium?
2.) Why did Justin feel that being an investor full time was not for him? How does Justin think about and approach the learning process as a founder? What advice does Justin give to those who want to quit? What was it that made Justin embrace the series of self-improvement habits he now practices?
3.) What does Justin mean when he says, "attaching yourself to outcomes will only cause your own suffering”? How does Justin think about and advise founders when it comes to burnout? How does Justin feel about the "crushing it" culture in tech? What can we do to normalise vulnerability? What were Justin's biggest takeaways from "The Score takes Care of Itself"?
4.) What have been Justin's experiences with therapy? How does he advise founders thinking of engaging with therapists? What have been his biggest lessons that drive success in therapy? How does Justin look to show authenticity through positivity? What does that really mean?
5.) What have been Justin's biggest takeaways from "The 15 Commitments of Conscious Leadership"? What are the core principles? What is required to roll out these values and principles within an organisation? What are the fundamental challenges to successfully roll this out on a large scale within your company?
Items Mentioned In Today’s Show:
Justin’s Fave Book: The 15 Commitments of Conscious Leadership
As always you can follow Harry, Justin and The Twenty Minute VC on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Jonathan Hsu is Co-Founder & General Partner @ Tribe Capital, one of Silicon Valley's newest funds on the block being founded by Jonathan, Arjun Sethi and Ted Maidenberg. To date, Tribe has invested in the likes of Carta, Cover, Mode Analytics, Prodigy and SFOX. As for Jonathan, before founding Tribe he was a Partner @ Social Capital where he utilized data and technology to augment sourcing, evaluation of investment opportunities and the management and value add for portfolio companies. Before that he led the creation of the analytics and data science team at Facebook, including leading the hiring of 200 of the world's leading data scientists and analysts.
In Today’s Episode You Will Learn:
1.) How Jonathan made his way from leading 200 data scientists at Facebook to the world of venture and founding his own firm in the form of Tribe Capital today?
2.) If we structure VC simplistically, there are 4 core components:
3.) Given the data-driven nature of the approach, does Jonathan think that there is an optimal portfolio construction? Why does Jonathan strongly believe that historical loss ratios are too high? Does data allow firms to really intelligently price these assets at the Series A and B? What are the challenges in pricing these assets so early?
4.) How does Jonathan think about reserve allocation? Why is data more critical than ever in the decision to re-invest or not? What are the leading data signals that Jonathan looks for when determining reserve allocation? Why does Jonathan think that so many firms go wrong in how they approach reserve management and distribution?
5.) Question from Henry Ward @ Carta: What does N of 1 markets mean to you Jonathan? Why are they so inherently attractive? How do pricing dynamics play out in markets that are N of 1? How does Jonathan think about defensibility when analysing opportunities today? Is anything truly defensible anymore?
Items Mentioned In Today’s Show:
Jonathan’s Fave Book: The Origins of Political Order: From Prehuman Times to the French Revolution
Jonathan’s Most Recent Investment: Carta
As always you can follow Harry, The Twenty Minute VC and Jonathan on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Brad Bao is the Co-Founder & CEO @ Lime, the startup that provides distribution of shared scooters, bikes and transit vehicles, with the aim to reduce dependence on personal automobiles for short distance transportation. To date they have raised over $775m in funding from the likes of Andreessen Horowitz, GV, IVP, Uber, Fifth Wall, GGV, Atomico and Bain Capital Ventures just to name a few. As for Brad, prior to founding Lime he was Managing Partner @ Kinzon Capital for close to 6 years and before that spent an incredible 8 years at Tencent in numerous different roles including VP of Business Development for Tencent Games and General manager for Tencent's US branch where he was responsible for Tencent's US operations.
In Today’s Episode You Will Learn:
1.) How Brad made his way into the world of technology with Tencent, how that led to the world of investing and then what was that a-ha moment for the founding of Lime? How did Brad's time with Tencent impact his operating mentality today with Lime?
2.) With significant levels of competition, how does Brad assess the competitive landscape today for micro mobility? Does Brad believe customer loyalty comes into play in the segment? Is capital itself a defensible moat in this market? Why is Brad adamant that it is important to spend $0 on marketing? What does this say about the product?
3.) How does Brad think about technological innovation within the space? Does it subscribe to Moore's law in the advancement of the core components? How does Brad think about inherent trade-offs that have to be made in product decisions? How does Brad think about prioritising for unit cost vs product superiority? Why can you not have it all?
4.) How does Brad think about launching new cities? What does it take to win in those geographies? What are all the necessary parts to setup when entering a new location? What is the biggest determinant of a location success? Density? Maturity?
5.) Brad has assembled a truly world-class exec team, what does Brad think it takes to attract truly A* talent? When should founders really start to think about building out their own exec team? What does Brad believe it is that makes his partnership with Toby Sun work so well? What have been his learnings from the development of that relationship?
Items Mentioned In Today’s Show:
Brad’s Fave Book: Good To Great by Jim Collins
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Scott Kupor is Managing Partner @ Andreessen Horowitz, one of the world's most renowned venture funds with a portfolio including the likes of Facebook, Airbnb, Github, Lyft, Coinbase, Slack and many more. As for Scott, he has been with the firm since its inception in 2009 and has overseen its rapid growth, from three employees to 150+ and from $300 million in assets under management to more than $7 billion today. Before a16z, Scott was a VP @ HP where he managed a $1.5 billion (1,300 person) global support organization for HP Software product portfolio. Scott joined HP as a result of his prior company Opsware, being acquired, where he served as a Senior VP across numerous roles across an incredible 8-year journey.
In Today’s Episode You Will Learn:
1.) How Scott made his way from the world of law to startups to being Managing Partner at one of the world's most renowned venture firms in the form of a16z?
2.) How did seeing the boom and bust of the dot com bubble and 2008 impact Scott's operating mindset today? Why does he argue that those times are so drastically different to today? How do public markets fundamentally diffferent? How do teams approach to capital efficiency and scaling differ significantly?
3.) What does Scott believe entrepreneurs get most wrong when pitching VCs? Why does Scott argue that product is not the core when pitching VCs? Does Scott agree with Fred @ Okta in weighing it: 70% market, 20% team, 10% product? What is Scott's weighting? Why does Scott believe that the compression of fundraising timelines is a problem? What pitch sticks out to Scott above all others? What made it so memorable?
4.) How does Scott advise founders on determining the right amount to raise for? Does Scott believe that founders should ask for a specific number or a range? Why does Scott believe raising for "runway" is the wrong mindset? Does Scott believe that most bridges are bridges to nowhere? If so, what is the next step? How does one relay that information to the founders?
5.) What have been some of Scott's biggest learnings from building the firm with Marc and Ben? What does Scott believe have been the biggest inflexion points in the public status of a16z? What have been the biggest challenges for Scott in the scaling of the firm? How does he foresee that changing in the future?
Items Mentioned In Today’s Show:
Scott’s Fave Book: Master of the Senate: The Years of Lyndon Johnson
As always you can follow Harry, The Twenty Minute VC and Scott on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Zach Perret is the Founder & CEO @ Plaid, the startup providing the easiest way for users to connect their bank accounts to an app whether it be transactions, identity or authentication. To date, Zach has raised over $300m with Plaid from some of the best in the business including Mary Meeker, Index Ventures, Andreessen Horowitz, Felicis, Spark and Homebrew, just to name a few. As for Zach, as CEO he has scaled Plaid to today with over 300 employees, 3 international offices and over 10Bn transactions analysed. Prior to founding Plaid, Zach was a consultant @ Bain.
In Today’s Episode You Will Learn:
1.) How Zach made his way into the world of startups from consulting at Bain and what led to the founding of Plaid and the mission to unlock consumer finance? What advice would Zach give to emerging grads today, questioning whether to join or start a startup?
2.) What does great leadership and CEOship look like to Zach? How has Zach seen himself evolve and develop as a leader over the last few years? How does Zach think about prioritisation? How does Zach determine what to say yes vs what to say no to? What has Zach found the most challenging in scaling as a CEO? What has he done to mitigate this?
3.) How does Zach think about constructing the optimal recruitment process? What have been some of Zach's biggest lessons in what it takes to really recruit world-class talent? What does Zach mean when he says, "you have to hire for spikes"? How does Zach manage the tension of keeping the high-quality bar whilst also sustaining the very steep growth curve?
4.) Plaid recently raised $275m, how does Zach think about capital efficiency with Plaid today? How does Zach determine when is the right time to transition from the mindset of lean and iteration to raising a war chest and going for the home run? What is Zach's biggest advice to founders when it comes to investor selection? Is it possible for the investor and the founder to be "friends"?
5.) When assessing the fintech landscape today, what is Zach most excited to see develop over the next 12-18 months? How are we seeing much larger incumbents like Goldman innovate in the proliferated world of fintech startups? How does the US view the fintech innovation that has occurred in the UK? What does this mean for US fintechs?
Items Mentioned In Today’s Show:
Zach’s Fave Book: Hard Drive: Bill Gates and the Making of the Microsoft Empire
As always you can follow Harry, The Twenty Minute VC and Zach on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Zach Coelius is Managing Partner @ Coelius Capital and in his own words, "a pretty eclectic investor who loves to see just about any deal". To date, Zach has made investments in the likes of mParticle, Cruise Automation, Branch Metrics, SkySafe, ProsperWorks and more. In addition, Zach is or has been an advisor to LiveRamp, Hellosign, Art19, Loom.ai, Survata and StartGrid just to name a few. Prior to his investing career, Zach was CEO @ Triggit, an online adtech company which he raised over $18m for and was ultimately acquired in 2015. If that was not enough, Zach is also a Senior Advisor to McKinsey & Co.
In Today’s Episode You Will Learn:
1.) How Zach made his way from the world of operating and adtech to investing and advising startups today? When does Zach feel the ecosystem really started to take him seriously as an investor? What did Zach learn from being in the adtech space that he has applied to his investing today?
2.) The Future of Venture: Naval has previously said we will see "the unbundling of VC", does Zach agree with this view? Why does Zach feel we are seeing both the bundling and the unbundling of venture platforms? What unique challenges does this pose for both sides of the equation? How should entrepreneurs evaluate the different options, bundled vs unbundled?
3.) Portfolio Construction: Why does Zach believe that portfolio construction is fundamentally inefficient? What 2 core areas of venture does portfolio construction cause issues for? When does Zach view to be the ideal insertion point if optimising for absolute returns and not following portfolio construction?
4.) Reserve Allocation and Pricing: Why does Zach think that the current mechanism for reserve allocation is broken? Why is it a fundamentally bias process? What does the optimal investment decision-making process look like to Zach? How does Zach think about the asymmetric information that is gained from being early into a company? How can investors really use it to their advantage? Why do they not?
5.) Why does Zach compare being an entrepreneur to being a gladiator and a rocketship? Why does Alex believe the transition from space articulation to product articulation is the most important thing an entrepreneur can do? What is the true sign of this transition in customer interactions? Where do many entrepreneurs make mistakes here?
Items Mentioned In Today’s Show:
Zach’s Fave Book: The Snowball: Warren Buffett and the Business of Life
Zach’s Most Recent Investment: Mud\Wtr
As always you can follow Harry, The Twenty Minute VC and Zach on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.