Square One: Conversations with the Best in Business

The world of private fundraising is going through a generational moment - meme stocks, NFTs and Robinhood. Everybody is looking to become an investor and with the right reason - the vast majority of wealth creation in the world has come from private assets, not public assets. The challenge historically, though, has been a lack of connectivity and access for the private investor. Private investors couldn't get involved, and the operational complexity for companies to take advantage of this investor base was too difficult up until now.  Enter Republic: an equity crowdfunding platform that's raised over 50 million dollars in venture capital to take on the status quo. This week, we chatted with Ken Nguyen, Co-Founder & CEO of Republic, to get his perspective on the business and the future of fundraising. 

This week we had David Sacks back on the podcast for round 2. There are few individuals in the world that have seen, built, and led multiple of the world’s iconic companies. David is one of them. He was a core member of PayPal and served as the company’s first product leader and COO. David went on to found enterprise collaboration company Yammer, one of the fastest-growing SaaS startups in history - Microsoft acquired Yammer for $1.2B just 4 years after its founding. Not only has David been a successful founder, but he has also been one of the most impressive investors in tech, having personally invested in over 20 unicorns, including Affirm, AirBnb, Facebook, Lyft, Opendoor, Palantir, Postmastes, Reddit, Slack, SpaceX, Twitter and Uber amongst others. I got David’s thoughts on building and scaling multiple multi-billion dollar companies.

This week we dove into the world of performance management - the last decade has seen significant change across virtually every function in business; the evolution of marketing, sales, customer success, product and operations departments has been tremendous. HR on the other hand, has been a laggard; historically a back office cost-center, typical HR organizations have followed the mandate of being compliant, administrative and "doing less."  This curve has started to shift materially over the last 5 years - we have a "war for talent" amongst employers and leverage has fundamentally shifted to the employee. COVID has provided a decentralization multiplier to this war and increased opportunity sets for talent worldwide.  In 2018, I had Jack Altman - Founder and CEO of Lattice - on the program to discuss how HR has evolved. Since then, Lattice has raised over $100M and recently hit a $1B valuation. I invited Jack back on the program to discuss the rocketship journey of Lattice and how his thinking on performance management has evolved after serving as an Executive in the space. This conversation was packed with insights on how to be an effective people leader. Enjoy. 

We’ve done a lot of deep diving into the infrastructure of e-commerce and marketplace on this show. We’ve explored shipping as an API and shipping infrastructure in developing countries. This week we took another spin on the topic - we talked about the cloud supply chain. Ok what does that mean? Simply put - if you had one software platform that could manage all of your fulfillment, shipping, warehousing and logistics needs - what would that look like? More importantly, what would it unlock for your business? I invited Sean Henry, Co-Founder and CEO of Stord to come on the podcast and break down these very questions. Stord is solving this exact problem and has raised over $150M to do it.  There are very few businesses where the proxy for market size is some variant of GDP - Stord falls in that bucket and it’s why I excited to learn from Sean this week.

Whenever you think of major cities in North America, they all have a vibe - NYC is legendary for Wall Street, San Francisco for Tech and LA for Hollywood. But over the last 25 years, one firm has blended the best of all 3 worlds: UpFront Ventures. Upfront is LA’s largest venture firm and has invested over $2B in startups across notable winners like Bird, Ring, thredUP, TrueCar and GOAT. This week I chatted with Kara Nortman, Co-Managing Partner of Upfront. Kara’s cool - she had a lot of unique insights on the state of venture and sports. A topic we nerded out on given Kara is one of the Co-Owners of Angel City, LA’s professional womens soccer team alongside her friends Natalie Portman, Julie Uhrman and Alexis Ohanian. Tune into this one if you’re into the crossover between sports, leadership lessons and tech. I learned a lot from Kara in this conversation.

The theme of the past year - in an obvious sense - has been how we continue to lead progressive, efficient, and normalized work lives in a highly unnormal world. The pandemic has forced us to rethink how we collaborate, engage and connect from first principles. One of the most ubiquitous products we all use in that effort is Dropbox - and it’s why this week I was thrilled to be joined by Timothy Young, President of Dropbox. Talking with Timothy was unique and interesting on multiple levels - on one sense, we dug deeply into the way Dropbox is reimagining the workplace and on the other hand we dove into how these changes in our work environment flow through the underlying products Dropbox is developing. We spent a lot of time talking about Dropbox’s new “Virtual First” strategy, how companies overcome friction when introducing new ideas, building the right model and environment for employees and the challenges of remote work - at the employee, team and management levels. I learned a lot from Timothy and this was one of the most engaging discussions we’ve had on the pod.

This week we dove into healthcare. Everybody listening has had a subpar experience with our healthcare system - whether it’s a friend, a colleague, a family member or a personal experience, our healthcare system is fraught with challenges. Part of the reason the system is so difficult is because of how the incentives are set up - patients, primary care physicians, specialists, health care systems, insurance companies have a web of complex intertwined interests. That’s also what makes it so interesting to tackle. This week’s guest was Sid Viswanathan, Co-Founder and President of Truepill. Truepill has created an API to help enable pharmacy fulfillment and delivery, white label packaging and product design. Their goal - simply put - is to create a pharmacy infrastructure grounded in technology and automation to build a next generation healthcare platform. Sid and team have raised over $100M to bring this vision to reality. In this conversation we discussed the challenges of innovating in healthcare, how Truepill provides customers with a better experience and the ups and downs of leading a hyperscale business.

One of the most transformational companies of the last 20 years has undoubtedly been Uber - in a sense it’s incredible to think in 15 short years we’ve come from the launch of the iPhone to now powering a global transport system with the click of a button on that same phone. This week I caught up with someone that was largely responsible for making that transformation a reality - Manik Gupta, Former Chief Product Officer of Uber. Manik and I spent time chatting about Uber, but also extended the conversation to leadership lessons and how he thinks about evaluating startups - we talked about how to think about resource allocation in hyperscale, the tradeoffs when developing product and the learning curve of leadership (he had over 1,000 people report to him in the span of 2 years). We rounded out the latter part of the discussion diving into an ecosystem both he and I have been actively investing in lately and are excited about - India.

We’re going through a renaissance period in consumer health right now - new tech enabled products are coming out for sleep, telehealth, diet, nutrition and more. This week’s guest took us deep into what optimizing the metabolic function looks like. As I learned in prep for this conversation, seven of the 10 leading causes of death in the U.S. are strongly related to metabolic dysfunction - metabolic function improves energy, endurance, memory, mood and cognitive performance. Josh Clemente has bought a biowearable metabolic sensor to market to help solve this problem - Levels is an innovative platform that pairs continuous glucose monitoring with an impressive software suite to provide the wearer with deep insights about their health. In advance of this conversation, Josh’s team sent my wife and I both a Levels to see how the product works and it was incredible - it provided us actionable health information and helped us understand how specific foods, exercise and timing of day affected our metabolic health. This episode was fun - Josh has experience at some of the most innovative companies in the world, like SpaceX and brought that experience to Levels to build a next generation category winner in healthcare.

We’ve talked a lot on this podcast about emerging and resulting trends that will stick with us a function of COVID-19: higher education being disrupted, consumer health being further tech enabled, the rise of crypto, and AI and machine learning impacting functionally every industry. But underneath the core of every industry we’ve talked about is people and global workforces. It’s why this week I was excited to chat with Alex Bouaziz, Founder and CEO of Deel. Deel is solving the incredibly complex and simultaneously important issue of global payroll. As workforces have gone remote and international over the course of the past year, Deel has developed software to help companies stay compliant with local laws and tax systems while keeping international onboarding smooth and seamless. Deel has raised over $200M over the past year and just publicly announced a $1B valuation.