Square One: Conversations with the Best in Business

One of my favorite writers (and thinkers) in tech today is Morgan Housel. Morgan consistently puts out some of the most provocative thought pieces and draws connections that routinely leave me wanting more. This week, it was a thrill to chat with Morgan. We touched a number of topics across philosophy, investing and psychology. Unlike many of our other episodes, I didn't have a few "favorite moments" - the entire conversation was filled with nuance and timeless perspectives.  Also check out these pieces from Morgan that we referred to in the conversation: The Psychology of Money, Immeasurably Important, The Lifecycle of Greed and Fear, Tails You Win, Useful Hacks. You can read Morgan's other articles and subscribe to his writing on the Collaborative Fund blog.

One of my favorite pieces for how to think about technology platform shifts is Chris Dixon's "What's Next in Computing". Chris notes that if we look at history, we see that irrespective of the way financial markets perform, technology platform shifts happen consistently every 10–15 years.  One of the most important platform shifts of the next decade is voice. Consumer markets have started to appreciate the strength of Alexa, Echo and Google Home but the recent demonstration of Google Assistant at Google I/O 2018 really expanded the imagination for what will be possible in a decade as deep learning and natural language exponentially improve.  Lately, I've been incredibly interested by the impact voice will have in the enterprise. This week, it was a thrill to chat with Omar Tawakol, one of the key players in today's enterprise voice landscape. Omar is the CEO of Voicea, a voice-activated AI for the workplace; he's raised $20M to leverage AI to augment tasks, make meetings more productive and create more efficient workflows. Eva (Voicea's AI-assistant) in actionPrior to Voicea, Omar was the founder and CEO of BlueKai which built the worlds largest consumer data marketplace and DMP. Oracle acquired BlueKai in 2014 & Omar led Oracle Data Cloud where he scaled the team to over 1,000 people and pioneered the ODC to become the leading Data-as-a-Service provider to 96 of the top 100 US marketers. Omar earned an MS in CS from Stanford (BS, MIT) where he researched and published work on AI agents. Check out the conversation and our other episodes on iTunes.

Coinbase. Slack. Affirm. Wealthfront. Medium. All generational companies with general founders. Each of these companies has gone on to become valued at $1B+ and have created lasting impact in their respective industries. As a venture investor, becoming involved with any one of these companies would be considered a grand success. Megan Quinn, GP at Spark Capital, has been involved with all of them. It was a thrill to chat with Megan. Aside from a successful investing career with both Kleiner Perkins, where she led a number of the firm's early-stage and growth consumer investments, and Spark Capital, Megan was an operator at both Square and Google. As Square's Head of Product, she led strategy and development of the company's products across merchant and consumer audiences. At Google, Megan spent seven years at Google where she held various leadership positions in marketing, business development and product management. She oversaw the development and launch of some of the company's most successful products, including Google Maps.  This conversation was a ton of fun. Megan and I discussed a number of topics including: (1) her infamous rise to Head of Product at Square (just 2 weeks after being hired in as Director of Risk), (2) her fascination with maps and her time at Google leading the Maps team, (3) investing in Coinbase and her outlook on crypto and (4) her important work as co-founder of the non-profit AllRaise.

Almost exactly a decade ago, a new bright eyed class of students entered Harvard Business School in September 2008. One month in, something happened that nobody could have anticipated: the economy completely fell apart. The world experienced the worst financial crisis since the Great Depression. At a time where the future looked uncertain and bleak and taking career risk was probably the last thing on any rational person’s mind, something magical happened at Harvard Business School. In just a short time window the foundation for multiple multi-billion dollar companies was being laid: Rent the Runway, Blue Apron, Plated, StitchFix and BirchBox.  This week I caught up with Hayley Barna, co-founder of BirchBox and current General Partner at First Round Capital. One of the famed consumer success stories of the last decade, BirchBox revolutionized the application of the subscription e-commerce business model to beauty and retail. Hayley helped the company raise over $80M in venture capital, generate $100M+ annual revenues and deliver products into the hands of over 1 million monthly subscribers. In her current role at First Round, Hayley is focused on finding the next crop of great consumer companies.  We had a lot of fun in this one — Hayley is one of the most personable guests we’ve had on the podcast. The conversation is filled with great lessons, but a few highlights included: (1) why the downside of taking risks is overrated, (2) how impact at scale is all about people and culture, (3) the importance of balancing growth with sustainability and (4) Hayley’s belief that the best thing you can do for yourself is “just getting out there and doing it”.

“Product-market” fit is one of the most ubiquitous and foundational terms in the startup community today. It’s a term that has inspired blog posts, books, curriculums, conferences and even plot lines of TV shows (turns out, its just as hard to find product-market fit in TV land). It’s virtually impossible to talk about products today without hearing reference to product-market fit; there are 400,000+ unique results on Google and over 5,000+ videos on YouTube explaining the concept.  It was a thrill to speak with the legendary executive and investor who coined the term, Andy Rachleff. Andy co-founded Benchmark Capital and led the single best performing early stage fund of all time. Benchmark has invested in an absolutely dynamite list of startups over the last 20 years: eBay, Uber, Twitter, Snapchat, Dropbox, Instagram, WeWork, StitchFix, Yelp, Zendesk, and Zillow amongst others. Over the past decade, Andy switched back to the operating side and founded Wealthfront. Today Wealthfront is the leading automated investment service in the market with over $10 billion in assets under management. We had a lot of fun in this one. This conversation was highly focused on Andy’s foundational work in product market fit, disruptive innovation and how these concepts serve as guiding principles in his work today with Wealthfront. The podcast is filled with great lessons, but a few highlights included: (1) why you can screw up everything if you have product market fit and still likely succeed, (2) how the best companies are founded with insight to a key inflection point in technology, (3) why the combination of being correct and contrarian drives the highest potential for value creation and (4) why failure is overrated.

Very few individuals in the startup community have seen deep success as operators, investors and community builders — it’s why this week I was so excited to chat with David Tisch. David is the Managing Partner of BoxGroup, an early stage venture fund in NYC; via BoxGroup, he has invested in a number of fantastic companies — GroupMe, Trello, ClassPass, Warby Parker and Harry’s amongst others. He also is the Founder and current Chairman of Spring, an e-commerce platform that recently raised $65M from Fidelity as well as the Head of the Startup Studio at Cornell. All three of his current roles, as well as his prior role in founding Techstars NYC give David a deep and thoughtful perspective on startups and technology.  We talked about a number of topics in our conversation related to the state of venture, startups and careers. Some of the most interesting perspectives David had centered around: (1) how technology has moved from a vertical to a horizontal, (2) what NY has doubled down on and how it has propelled to become a world class innovation hub and (3) how defining yourself is about more than just your pedigree.

“Amazon is eating the world” is today’s conventional take for retail outsiders. It’s certainly a position I espouse and it’s why this week I was so excited to chat with Jerry Storch. Jerry most recently was the CEO of Hudson’s Bay Company and previously was CEO of Toys R Us and Vice Chairman of Target. Jerry is known in the world of retail for his forward thinking on technology and has embraced technology heavily as a Senior Executive. At Target, he founded and led the e-commerce strategy of target.com, at Toys R Us he expanded the e-comm business to over $1 billion and led international expansion into China, and at Hudson’s Bay he drove the acceleration of the all-channel e-comm business model.  We talked about a number of topics in our conversation related to technology and retail, leadership and careers. Some of the most interesting perspectives Jerry had centered around: (1) the importance of thinking through big bets via first principles, (2) why the debate around AI and it’s impact on society should be reframed to a short term discussion on displacement and a long term discussion on growth, and (3) how learning in 2017 is all about being a maniacally vociferous reader. 

Snap. Warby Parker. Airbnb. Stripe. Kayak. That list of companies has a two clear things in common: (1) they are all generational companies that have contributed to significant value creation and (2) General Catalyst invested in all of them. This week, we dug deep into what’s going on in the world of venture with David Fialkow, Co-Founder and Managing Director at General Catalyst. David had an interesting journey to venture — successfully founding and exiting four companies — and ultimately created an early-stage fund to give the type of support to entrepreneurs he sought as a founder. My favorite moments in this conversation included David’s reflections on: (1) how to think about aligning founder and VC interest, (2) why going public is overblown and (3) why at the end of the day, nothing matters more than people .

Venture capital is hard. Startups are brutal. The media has turned the winners of innovation into mythical heroes often glorifying the end result over the struggle of the process. Is this good or bad? What are the implications for the broader tech industry? What about for the hordes of individuals encouraged to enter a race where the odds are stacked against them? This week I had a fiery and candid conversation with Jason Lemkin on these very topics. Jason is a SaaS legend - he's a 2x successful founder, current Managing Director at SaaStr Fund, and runs SaaStr Annual, a community of over 10,000 founders, investors and executives focused on B2B SaaS.  This conversation was candid as ever and Jason debunked the ease that startups and venture capital are often portrayed with. My favorite moments included: (1) the importance of atomized thinking when it comes to tackling challenging problems, (2) the inherent challenge for big companies in sustaining and supporting innovation and (3) why your team is the most important decision you can make as a founder.

Hiring correctly and operating proficiently are two of the most complex and nuanced management skill sets necessary to lead an organization to success. This week, we dived into these topics much more deeply with Keith Rabois, General Partner at Khosla Ventures. Keith is a member of the famed PayPal Mafia — having worked closely with Peter Thiel, Elon Musk and Reid Hoffman amongst others in his early days — and has become a revered source of how to successfully hire and execute in Silicon Valley. Keith held Executive roles at PayPal, LinkedIn, Slide and Square prior to joining Khosla Ventures.  This conversation was a ton of fun and we talked through a bunch of different topics, some of which included: (1) how to think through hiring and retaining talent, (2) the characteristics of world-class leaders and (3) the need for organizational transparency and laser-pointed focus at the highest levels. One of my favorite parts of the conversation was our “lightning round” at the end, where Keith gave his thoughts on which of today’s largest tech companies will be least influential in the future, whether or not Silicon Valley remains the world’s innovation hub going forward, and the best pieces of advice he ever got from Peter Thiel, Elon Musk, Reid Hoffman, Vinod Khosla and Jack Dorsey.