Square One: Conversations with the Best in Business

Julien Smith is one of the most direct, thoughtful and intense Founders I've had the pleasure of having on the show. Julien founded Breather in 2012 and has since raised $150M+ to build out the business. He's the New York Times bestselling author of three books. Two of these, Trust Agents and The Impact Equation, were written with Chris Brogan. The third, The Flinch, has consistently remained one of the top read Kindle books since it was published in 2011. Having Julien on the show was a pleasure - he's extremely original in thought and has some of the best content on the internet. We talked about his article "The Complete Guide to Not Giving an F", the importance of showing up, failing your way to the top, self awareness, and how we as a tech community can generally improve. This episode was a blast. 

For an industry that has made its mark on funding disruption, venture capital hasn't changed much over the past 30 years. With new entrants (cue: Softbank) and discussions about venture dollars primarily pouring into real estate and customer acquisition, it has become more common to question whether venture capital is the right type of capital for all stages of a business. Why do we treat businesses as black and white binary entities? Equity or debt. That's it. Enter Clearbanc - Clearbanc is building an alternative capital source for entrepreneurs. The company has raised $300M+ and funded thousands of entrepreneurs. Andrew and I chatted about why Clearbanc is a truly differentiated source of capital, at what point is it most applicable and when does it become more preferable to traditional equity or debt.  Clearbanc's innovation has significant potential implications for the entire venture market. If you believe in the premise that equity capital is best suited to fund risk and experimentation and a new source of capital (a la what Clearbanc provides) is best suited to fund repeatable growth, a new asset class has the potential to right size how we think about segments of capital markets. Our conversation extended well beyond the nuts and bolts of the capital stack - we got knee deep into startup operations. We talked pivots (Clearbanc started the business focused on Uber drivers!), hiring, building in Toronto and the pros/cons vs. being based in Silicon Valley, unique operating practices at Clearbanc and why the company's culture is a mix of Lululemon and Bridgewater.

Today’s guest is Auren Hoffman, Former CEO of LiveRamp and current CEO of Safegraph. Auren has had one of the most storied careers of SaaS founders in the Valley and is known for having an often unique and contrarian perspective. In this conversation we discussed why the best businesses are at the intersection of value creation, personal advantage and a contrarian perspective; whether businesses should target niches or broad markets; and the advantages of being older as computing power becomes more powerful.

Elad Gil really needs no introduction - he’s been integral in some of the most interesting and iconic companies in the valley. After fulfilling a PhD at MIT and a brief stint at McKinsey and Company, Elad went on to join Google and Twitter through their hypergrowth years; he joined Twitter when there were 90 employees and two and a half years later, he had helped the company scale to 1,500+. Elad is the founder and former CEO of Color Genomics and has invested in 20+ companies valued today at over $1B, including Airbnb, Coinbase, Checkr, Gusto, Instacart, OpenDoor, Pinterest, Square, Stripe and Wish. This episode was a ton of fun - I talked to Elad about his perspective on industry towns, why there aren’t many founders that come from Amazon, Microsoft, or Apple , his genomics research, how he evaluates companies and what are the most counterintuitive principles he taken away from investing in over 20 unicorns.

In Silicon Valley today, it’s become a phenomenon to talk about raising less venture capital and going remote to offset capital cost and get better access to talent. This wasn’t always the dominant perspective; in fact it was often looked upon as an inhibitor to building a great company. Zapier - founded roughly a decade ago - has turned those two principles, amongst others on their head. Today the business has (still!) raised less than $1.5M, just recently crossed $50M in ARR and has been fully remote since Day 1. This episode was a ton of fun - I talked to Mike about how him, Wade and Bryan founded the company, their original vision for the business and how it has transformed a decade later, and how they have successfully led a remote company. Mike’s authenticity is audible in his voice - it was great to hear his very candid and humble perspective on building a once in a generation company.

You don’t have to search high or low in the tech community to find tips and tricks on every function in a business - product, engineering, fundraising - it’s all out there. Only recently have mindfulness, leadership and mental health become top topics that founders and investors have started systematically talking about. In this episode I talked to one of the best advocates of mental health and coaching in the tech community today - Steve has a unique perspective on coaching early stage founders and we talked about the challenges and opportunities in the space. Steve is a trained executive and performance coach. He works with founders and executives to help them fulfill their potential as leaders inside and outside their organizations. Steve decided to pursue a coaching certification because he had a strong desire to engage with founders more deeply and develop stronger relationships based on respect, trust, authenticity and vulnerability.  Steve’s words are important for all folks in the tech community to be better leaders. Steve has had a storied career as an investor. He has been investing in the NYC tech ecosystem for the last decade. He straddles B2B and B2C with a bias toward the weird. His human centric approach to investing has enabled him to lead investments in Giphy, Bowery Farming, Brightwheel, Groups, Boom Aerospace, Care/of, Citizen, Wag!, theSkimm, Breather, View The Space and many more.  This episode was a ton of fun - Steve's authenticity is audible in his voice. It's no question why he's been such a great champion for founders.

Data driven venture capital is a controversial topic with strong opinions attached. The classic rebuttal of data driven VC is the idea that successful early stage startups look wildly different and so even if you do capture clean data, there is a fundamental skew (e.g. either you misplace predictive importance on certain variables or your data set is not large enough) so the outcomes would be falsely comforting. On the other side of the coin, however are venture firms that have not only positioned themselves as data oriented firms, but have broken through this narrative and realized outstanding returns as a function of this orientation.  Enter Switch Ventures. A seed stage venture fund focused on identifying the most talented startup entrepreneurs through data science. Paul Arnold, founder of Switch, has longstanding experience applying data driven strategies with C-Suites, Boards and front line employees to drive change. He was a senior executive at AppDirect and helped build it into the unicorn it is today; prior to AppDirect, Paul was with McKinsey & Company in Silicon Valley.  It was a pleasure to have Paul on the podcast. We talked about a number of topics in this episode. Some of my favorite, included: (1) the early days of Switch, (2) his data driven investment approach, (3) how his approach has evolved as he’s gained more experience as an investor and (4) where he believes the future hubs of innovation will be.  Follow Paul’s writing on Forbes and get in touch with his team at Switch if you’re building a company and interested in his approach.

The rise of SaaS has liberated the enterprise stack. Products are now brought into an organization at the atomic level and decentralized decision making has enabled modern tech companies to move incredibly quickly to solve specific problems. The challenge of this speed however is the complexity that a web of unrelated applications creates.  Glossier, a recent entrant to the unicorn club, uses 14 different analytics tools across 12 different platforms such as their website, their mobile app and their brick-and-mortar store. Each tool has its own copy of the customer data and history of privacy preferences; the complexity to uncover key insights becomes an impediment to how effectively a business can operate.  Enter Segment. The analytics tool to end all integrations. Segment has raised over $250M from leading investors including Accel, Google Ventures, Y Combinator Continuity Fund and Thrive Capital. Segment raised its Series D ($175M) last month and the venture community is excited about the company being the defacto layer of stitching together disparate customer data for organizations.  It was a pleasure to have Peter on the podcast. We talked about the early days of Segment, pivoting with only $100K left in the bank and scaling a business that has now raised over $250M. Some of my favorite moments included: (1) how Peter thinks about speed vs. process at different junctions of growth, (2) the characteristics of true product market fit, (3) how Peter has shifted his time as the company has scaled and (4) the unique value system that has been implemented at Segment.

“Data is the new oil” has become one of the most common catch phrases in popular media. It makes sense right? Wrong. At least according to Ash Fontana, Managing Director at Zetta Venture Partners and one of the most nuanced thinkers on AI today.  Ash believes we are squarely in the fourth era of computing, the intelligence era. In this era, data aggregation is less interesting than matching data sets to tactical problems. And with good reason. The intelligence era is an inflection point; traditional I.T. infrastructure will change to enable the development of self-learning software and previously data-starved markets — from agriculture to sales — will benefit from the information generated by self-learning software.  Ash thinks about AI companies with an incredibly human centric approach; when he evaluates data sets and companies, he asks how much human activity can the company free up if it works at scale.  In this episode, we chatted all things AI with Ash. We talked about a number of topics; some of my favorite included: (1) the utility of data for AI first companies, (2) why data strategy is fundamentally different for an AI driven company vs. a normal software company, (3) why Ash is bearish on SaaS and (4) how do you compete with Google, Amazon and Facebook in a data driven world. It was a pleasure to have Ash on the show to get his thoughts on the future of AI. His perspective was incredibly thoughtful and I personally learned an incredible amount from him in this conversation.

Joe Rogan gets more views than CNN. Kylie Jenner is dominating cosmetics (with less than 30 employees). Conor McGregor can sell more PPVs than UFC. So what’s going on? The labor markets we are living through today are at an inflection point. The age of the individual is on the rise and AI is automating away “old world” jobs, while increasing leverage for “new world” jobs. The McKinsey Global Institute did a study on looking at characteristics and occupations that could be automated away; the conclusion was that we are in for a significant shift over the next 20 years. This week I chatted with Brianne Kimmel on all things future of work.