Square One: Conversations with the Best in Business
By Romeen Sheth
Square One is a podcast where we interview founders, investors, and executives at the cutting edge of business. We discuss industry topics, careers and the journeys of how these individuals got to where they are today. We start at Square One.
Childcare is fundamentally shifting - the share of households where both parents work hit 66% in 2016, up from 49% in 1970, according to the Pew Research Center.
Sara Mauskopf is the CEO and co-founder of Winnie (https://winnie.com), a marketplace for child care built on powerful data systems and backed by a trusted community of parents and providers. Parents use Winnie to discover high-quality local daycares and preschools and learn all about their programs including detailed descriptions, photos, tuition information, licensing status, availability data and more. Child care providers use Winnie to fill their open spaces, build their wait lists, and get support and resources to run their business efficiently.
Winnie was started in early 2016 when Sara became frustrated with the long search to find child care for their young children. Now Winnie is used throughout the United States and is helping connect millions of parents with high quality child care.
This conversation was one of the most genuine we've had on the podcast - Sara talked fundraising while pregnant, why Winnie is for ALL parents and not just moms, equality in the workplace and equality at home, and what keeps Sara down to earth maintaining perspective while running a high growth company.
There's a lot of noise in the venture ecosystem today on differentiation. When I think of a venture firm that defines differentiation, I think of First Round Capital. This week I chatted with Phin Barnes, General Partner at First Round, on a whole host of topics. Phin brings a unique operating background to the table - he spent six years helping to scale AND 1 Basketball from $15 million to over $225 million in revenue. - and has scaled this experience to a number of fantastic companies. In this conversation we discussed:
- Intentionality and why the best Founders have it (specifically he referenced Notion, Modern Fertility, Steady, Clearbit)
- Initially working for free for First Round Capital with no intent to ever become a Partner
- The importance of moving slow and challenging the cult of speed
- Success being found in moments of discontinuity vs. continuity
- Compensation for judgement vs. time
- Tech enabled businesses vs. pure play software businesses (e.g. Peloton, WeWork)
- Pattern recognition as a code for intellectual laziness
- Measuring learning on a "per dollar" basis
- Why diversity isn't talked about enough and how he wants to change that
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.
Austin Rief is the Co-Founder and COO of the Morning Brew, a daily newsletter delivering witty business news to 1.5mm+ subscribers. Austin and his Co-Founder, Alex Lieberman, started the Brew as Michigan undergrads, running it as a side project until 2017. The early Morning Brew was a PDF for college students in need of news talking points for finance and consulting interviews. In 2017, Austin and Alex pulled the trigger, walked away from Wall Street, and started Brewing full time. Austin and I discussed his approach to early hires and the impact they have on setting company culture, the future “nichification of everything”, the pitfalls to taking VC money and why some founders would be better off steering clear, growth hacks the Brew employed to break a million subscribers, an increasing focus by consumer brands on LTVs, and more.
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.
On this episode, we spoke with Teddy Fusaro, the COO of Bitwise Investments, which provides index investment products for cryptocurrency.
Teddy’s a finance veteran, starting his career with Goldman’s synthetic products group at the height of the financial crisis, which had a dramatic impact on his view of the financial industry. From there, Teddy led ETF initiatives for two companies, converting relatively complicated products into funds for Main Street investors.
Among other things, we discussed his framework for evaluating crypto companies (critiquing the team for a good mix of technical and business backgrounds), the demand for traditional index products despite the purity of crypto self-custody, Bitwise’s core growth channels, and the importance of leading with education to sell investment products.
Hossein Azari and Dana Panzer are co-founders of cmorq, a start-up focused on making reliable blockchain data more accessible.
We’ve spent a lot of time on prior episodes discussing the infrastructure around cryptocurrencies as a hurdle to widespread adoption. The team's goal through cmorq is to free clients from the costly and time-intensive process of setting up and maintaining nodes on public blockchains, the only way to access compliant, real-time feeds today.
Hossein and Dana have been brainstorming about businesses they could start together since they met at Columbia Business School, where in 2016 Hossein first convinced Dana to invest in crypto. This past fall, they came up with the thesis behind cmorq.
Get ready for some candid takeaways, including counter-intuitive advice on hiring, parallels between an academic mindset and entrepreneurship, the data challenges faced by companies working in and around public blockchains, and more.
You can learn more about cmorq at www.cmorq.com.
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.
Paul Veradittakit is a Partner at Pantera Capital, a leading digital currency investment firm. Before Pantera, Paul worked in venture capital at Strive Capital, in consulting and research roles, and served as an advisor & mentor to a bunch of interesting companies.
The emergence of digital assets opened up a whole new asset class for investors, along with a new generation of companies working on infrastructure and user interface solutions for retail and institutional users. Paul was one of the early cryptocurrency adopters, joining Pantera in 2014 when Bitcoin and other cryptocurrencies were still fringe technology to mainstream investors, best known for the Silk Road and Mt. Gox.
On this episode, Paul and I discussed:
(18:48) Differences in approach to investing in digital currency projects versus more traditional early stage companies;
(21:46) Pantera’s current focus on infrastructure-oriented projects working on scalability solutions;
(33:49) Paul’s framework for initial exchange offerings as a replacement for the current initial coin offering (ICO) process;
(40:44) The potential for cryptocurrency to improve financial access in emerging markets;
...and much more.
Check out Paul's newsletter at medium.com/@veradiverdict for more interesting content. Share any thoughts on this episode through Twitter @squareone_pod or @alexrienzie, or email firstname.lastname@example.org.
While the public's attention in 2018 was focused on crypto’s price collapse—following a record bull run in 2017—an army of builders and executives were laser-focused on advancing crypto’s infrastructure and user interface to further accessibility and user adoption.
As President and Chief Legal Officer of Blockchain, which provides tools to send, receive, store and trade cryptocurrencies, Marco led efforts to advance utility in the ecosystem. Previously, he was a partner at Cooley—where he built leading fintech and digital assets businesses—and authored the SAFT whitepaper, an initial coin offering standard analogous to SAFE for private equity raises.
Our conversation touched on decentralized applications (dApps) and hurdles to mass adoption; crypto regulation in the US, UK and EU; non-fungible tokens; security tokens and state law initiatives; and more.
We really enjoyed this conversation and hope you do too!
Share any thoughts on Twitter @squareone_pod or @alexrienzie; or email email@example.com.
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 notorious as a society for falling in love with the next “fitness fad.” Whether its diet types, workout regimens or new fitness equipment, we’re suckers for “quick fix” schemes. It’s pretty rare that we come across a product that revolutionizes the way we workout — and in the age of connected hardware and software — we’re living through a paradigm shift that allows us to reimagine the fitness experience from first principles.
This week, I got the chance to chat with Brynn Putnam, Founder and CEO of Mirror, a connected fitness system that streams live and on-demand classes to users in-home via a sleek responsive display. Mirror enables users to train with experts, work out with friends and get real-time personalization.
The confidence from the venture community for Mirror runs deep — the company has raised $40M+ from leading investors, including Spark, First Round, and Box Group — and it’s easy to see why. The market is huge, the product is fantastic and Brynn is an incredibly thoughtful leader. I found many of her reflections insightful; specifically it was most interesting to hear her talk about: (1) running a combined hardware, software and content business, (2) thinking about the business as a “media company” vs. a “technology company” and (3) the pathway to evolve Mirror from a fitness business into “the defacto screen in your life.”
It was a pleasure to have Brynn on the show to get her thoughts on the future of connected home. This is going to be a fun company to follow.
The future of education and skilling is becoming very interesting. When you apply first principles thinking, the classroom experience, curriculum and economic model are all up for grabs. This week I chatted with Shaan Hathiramani, Founder and CEO of Flockjay, a 12 week immersive online sales academy that only charges students IF they secure a $50k+ job upon completion of the program.
We hear a lot about bootcamps in tech and the idea of the income share agreement is becoming a more popular way to align incentives, but we have yet to see these concepts married together for sales. So what inspired Shaan to start the company? He spoke with 250 universities and asked them a simple question “Did they have any courses that teaches anything related to Salesforce?” A resounding “no” empowered his belief that college curricula and the necessary skillset to be productive in the marketplace was out of balance.
I got a chance to learn more about Flockjay’s current cohort and the backgrounds of the students are incredibly inspirational. Some are first generation Americans, some have done tours in Afghanistan and some grew up in foster care. The coolest part about Flockjay is it works for all demographics, all ages and all backgrounds. All you need is grit.
It was a pleasure to have Shaan on the show to get his thoughts on the future of skilling. Watch out for this company — Flockjay is going to be really interesting to watch over the next decade.
The global stock of institutional grade real estate is set to triple over the next 15 years, with some estimates pegging aggregate values at ~$70 trillion. With this increase in asset volume, there’s a slew of complexity and change on the horizon — social migration will change the distribution of construction, the changing nature of cities presents a wider range of risk and return opportunities and technology is playing a deeper role in we re-think the physical world.
Though there’s significant macro change on the horizon, participating in the market today feels less than inspirational — transacting is expensive, messy and lacks transparency.
Enter Opendoor. Opendoor brings machine learning and a thoughtful user experience to bear to dramatically simplify the end-to-end residential real estate transacting process. The company has raised $500M+ over the past few years and has scaled to 1,000 employees in less than half a decade. JD and I chatted at length about: (1) the technological shifts that make Opendoor possible, (2) key lessons he’s learned in scaling a business so quickly, (3) the flywheel effect for Opendoor and why its different from other marketplace businesses, and (4) the challenges incumbents face in entering this space.
It was a pleasure to have JD on the show.
In an age of speed, overstimulation and FOMO, it’s easy to get caught up in the latest tech trend. This mindset doesn’t discriminate and is often most pervasive amongst the most sophisticated people in the world. Over the past year, I’ve had a number of conversations with Fund LPs and often I hear comments like “What crypto investments should we make?”, “When will VR take off?” and my favorite “Did this fund invest in a scooter company yet?”
It would be naive to write off any of those sectors and think that massive value won’t be created by the winners in those spaces. What I find most interesting though is how little airtime we give to the massive sector of value creation that lives and breathes on the complete opposite side of the spectrum. These are not the businesses that will 10,000x their value in 5 years, but they are ones that print material and consistent cash flow over outsized periods of time. Or as our guest in Episode 35 likes to call them: “boring businesses.”
Brent Beshore is the Founder and CEO of adventur.es, a extremely unique PE firm in Columbia, Missouri. Brent has raised $50M of capital for his fund and partners with entrepreneurs with the intention to never sell his ownership stake. We chatted at length about boring businesses, evaluating fads vs. trends and some of his biggest philosophical learnings from looking under the hood at over 12,000 companies.
It was a pleasure to have Brent on the show. He’s undoubtedly a sharp investor, but he has a refreshing amount of empathy which I appreciate the most.
“First principles” thinking gets a lot of lip service today in technology and venture capital. While its in vogue to acknowledge this way of thinking, very few actually adhere to it in practice. In Episode 34, I chatted with Ali Hamed, Managing Partner at CoVenture — one of the most “first principles” thinkers I’ve had the privilege of speaking with and hosting on the show.
In this episode, Ali opened up what is possible when you think creatively — whether its how to structure a firm across multiple asset classes (lending, venture capital and crypto), invest in new digital asset classes (e.g. rolling up Instagram accounts) or evaluate a company’s progress (debunking the fallacy of MRR and growth thresholds necessarily indicating progress). Ali covered it all in this conversation.
It was a pleasure to have Ali on the show. He pushed my thinking through the conversation and I learned a lot from him.
As software eats the world, the idea of moats and the power of compounding have taken a new turn of influence. In Episode 33, I chatted with Leo Polovets, General Partner at Susa Ventures on the importance of these two fundamental concepts and why they are so powerful, but yet still so counterintuitive in 2019.
In this episode, Leo expanded on his experience from being one of the first dozen employees at LinkedIn to experiencing hypergrowth at Google and how this has enabled him to find and support the next set of generational companies, e.g. Robinhood, Flexport, Andela and LendUp. He expanded on Susa's investment thesis in funding entrepreneurs that are building highly defensible companies that leverage data, economies of scale, and network effects to build value and achieve longevity. We also touched on nuanced philosophical concepts in company creation such as "position vs. momentum" and "ego vs. perception."
It was a pleasure to have Leo on the show. He's one of the most thoughtful venture investors I've had the privilege of getting to know.
Caitlin Long is a thought leader in the cryptocurrency & blockchain community, having been the Chairman and President of Symbiont - -an enterprise blockchain company - -and co-founder of the Wyoming Blockchain Coalition. Before 2016, Caitlin spent 22 years on Wall Street, with roles across Morgan Stanley, Credit Suisse, and Salomon Brothers. She has been active in bitcoin since 2012.
In this episode, Caitlin provides her perspective on the benefits of Bitcoin as a global reserve currency, the ability of incumbents to counter Bitcoin at this stage of its evolution, and the market structure benefits of blockchain and security tokens for traditional asset classes.
Today, the mental health crisis has reached a tipping point - one in five adults has a mental health condition and over the last 20 years there has been a 30% increase in suicide rates and 130% increase in depression amongst young adults. From a economic perspective, we're facing a staggering ~$200 billion in lost earnings (per annum) attributed to mental illness. In many ways, there are troubling signs that these numbers will actually get worse - these conditions are further exacerbated by two phenomena: (1) uneven access to mental health services (the Mental Health America study found that 50+% of Americans don't have access to basic services) and (2) the stigma against mental health (many don't get the care they need even if they have access, because of the associated label).
Despite the sheer size and growing demand for services, (e.g. over 2.5 mental health providers for everyone one primary care physician and a labor market growing 25% per annum), the space is incredibly fragmented and underserved. NYC alone has a staggering 90% of its providers working as solo practitioners. The lack of sophistication, quality of user experience and shortages that follow sub-scale practice add up.
In Episode 31, we unpacked all these dynamics and how software and design play a pivotal role in improving the patient and provider experience with Harry Ritter, Founder and CEO of Alma. Alma is a new practice model for therapists designed to elevate the therapy experience and simplify access to great care. It was a pleasure to have Harry on the show to discuss this distinctly important topic.
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."
However in 2018, this is all changing. In a world where the leverage in the "war for talent" has shifted to employees, HR is becoming a strategic asset; companies are understanding more and more they are above all in the people business. This mindset shift has pushed HR to focus on employee experience, improving engagement and overall organizational health.
In Episode 30, we unpacked all these dynamics and how software plays a pivotal role in the new HR world-order with Jack Altman, Founder and CEO of Lattice. Lattice offers an elegant user experience on the front end with a rigorous data engine on the back-end to help organizations drive best in class performance management. It was a pleasure to have Jack on the show.
In 2018, Uber is a household verb. The company is on an absolute tear; Dara Khosrowshahi has assembled a world class management team and Uber is evolving from a ridesharing company into a full scale transportation business. The company now has multiple business units at multi-billion dollar run rates; earlier this year Uber announced Eats is at a $6B+ bookings run rate. Excitement around the company is steep and in 2019 we are likely to see an IPO. The early view on pricing is Uber will enter the public markets at $100B+ market cap.
Back in 2011 however, Uber was anything but a foregone conclusion. The company had raised a small Series A and the incumbent taxi industry threw everything they had at the business. Fights were prevalent in every market, but the battle in New York City was especially high stakes. The world was watching New York and if Mayor DeBlasio succeeded in shutting Uber down, it was only a matter of time before the rest of the world followed.
Founder and then-CEO Travis Kalanick engaged Bradley Tusk to help with the fight. One of the most public and epic battles between private enterprise and city hall, Bradley ran a genius political campaign that ultimately kept Uber up and running as a business. We unpacked how it all went down in Episode 29.
It was a pleasure to have Bradley on the show; we spent most of the time chatting about Uber, but we also touched on how he's using blockchain to empower mass mobile voting - a key initiative to fix low voter turnout - and whether his former boss Mike Bloomberg will run for President in 2020.
Education is broken. Since 1996, only three sectors have materially risen when adjusted for inflation. Construction is a bit more expensive than the inflation benchmark, healthcare and childcare prices have risen ~2x the benchmark, and college education has risen 4x inflation!
This rising cost is having a significant impact on the economy - millennials are less likely to start businesses, own homes and are taking longer to "settle down" due to the crippling impact of student loans.
A lot of companies have been trying to disrupt the higher ed space; one of the companies I've been most impressed by in the space is Lambda School - a 30 week immersive coding school that only charges students IF they secure a $50k+ job upon completion of the program. Lambda is one of the fastest growing startups in the Valley and just announced a fresh round of capital this week, led by Google Ventures and Stripe.
It was a pleasure to have Austen on the show to get his thoughts on the future of education. Watch out for this company - Lambda has the potential to be one of the most important and impactful companies in the next 20 years.
Kavita Gupta is a leader in the Ethereum community, investing in seed and pre-seed companies through equity and tokens for ConsenSys Ventures, the VC arm of the Joseph Lubin-founded blockchain venture production studio focused on the Ethereum ecosystem. Kavita and I discussed plans for ConsenSys Ventures' $100mm second fund (20:50)--the first accepting external capital--their new Tachyon accelerator (18:40), temperature of investors in the crypto/blockchain market, evolution of enterprise vs permissionless blockchains, and much more!
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. In Episode 26, 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.
Kyle Samani is well known as a thought leader in the crypto community, often taking unique positions on development efforts in the space. He's a founder and managing partner of Multicoin Capital, a ~$75mm fund investing in tokens and equity. Before Multicoin, Kyle founded Pristine, a start-up that built software for Google Glass for use by surgeons.
In Episode 25, we spent some time discussing Kyle's excitement for zero knowledge proofs, which -- in addition to enabling selective disclosure between distrusting parties --have the potential to exponentially improve protocol efficiency through data compression, a game-changing innovation in the ongoing struggle to scale public blockchains.
We also discussed some of the key scaling initiatives being pursued by Bitcoin & Ethereum core developers - -i.e. Lightning, sharding and state channels--and his concerns on prospects for timely adoption; Kyle's framework for analyzing protocols and their addressable markets; and Multicoin's approach to portfolio construction, among other topics.
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. In Episode 24, 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 Voicera, 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 (Voicera's AI-assistant) in actionPrior to Voicera, 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 in Episode 23. 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.
Tim Draper is a legendary investor and the creator of “viral marketing,” an instrumental method employed by countless startups. He founded DFJ in 1985, now one of the most prominent venture firms in Silicon Valley, ultimately leading investments in Skype, Hotmail, and Tesla, among many others.
Tim was an early advocate for Bitcoin, long before cryptocurrency became popular in conventional tech circles. In this episode, Tim and I discuss competition amongst cryptocurrencies and Bitcoin’s ability to rise to technical challenges; likely regulatory actions and potential competition between governments to attract crypto talent; and broader applications for blockchain technology, among many other topics. We also discussed some blockchain projects about which Tim is particularly excited: Tezos, Bancor and Credo, among them.
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.
In Episode 21, 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”.
Erik Voorhees is a name synonymous with Bitcoin and cryptoassets. Among Bitcoin’s earliest adopters, Erik’s passion led to him to found multiple successful companies, among them Coinapult and Satoshi Dice, two of the first Bitcoin applications, and ShapeShift, a leading cryptoasset exchange. Erik is also one of crypto’s true visionaries, which is why I was so excited to chat with him for Episode 20 of Square One.
Erik and I discuss some exciting projects on the horizon, including privacy coins and SALT Lending; community governance issues that came to light through Erik’s advocacy for Bitcoin’s SegWit and increased block size; the tokenization of securities; regulatory pressure and community self-governing solutions; and much more.
“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.
In Episode 19, 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 in Episode 18 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 in Episode 17 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.
Check out other conversations with business leaders by subscribing to the Square One podcast on iTunes.
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.
In our sixteenth episode, 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? In our fifteenth episode, we 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.
Shadow banking, or lending by non-bank financial institutions, has continued to expand in the years following the financial crisis, as non-bank lenders provide a critical service to mid-sized companies in need of capital. In our fourteenth chapter, we caught up with Howard Widra, Apollo’s Head of Direct Origination, who built multiple businesses in the middle-market lending arena. Over his career, Howard ran businesses that were integrated into GE Capital, Merrill Lynch and, now, Apollo Global Management — an alternative asset manager with over $200bn in assets under management.
Our conversation touches on a range of topics, including (1) corporate culture across fundamentally different types of organizations, (2) macroeconomic head/tailwinds and their impact on middle-market lending, (3) healthcare reform, and (4) practical tips on taking early risk for students and young professionals.
Hiring correctly and operating proficiently are two of the most complex and nuanced management skill sets necessary to lead an organization to success. In our thirteenth episode, 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.
In our twelfth episode I chatted with Jim Feuille, General Partner at Crosslink Capital. Jim joined Crosslink after a successful career in finance, previously serving as Global Head of Technology Investment Banking at UBS. Over the past 15 years in venture, Jim has invested in successful teams at Omniture, Ancestry.com, Coupa and most notably, Pandora.
Jim and I covered a number of topics in this one; ranging from Pandora and the state of the consumer internet in 1995 to capital allocation in venture today and what new entrants (i.e Softbank and their $100bn Vision Fund) are thinking. Some of my favorite moments included: how the Crosslink team was able to source Pandora (11:55), why the freemium model was core to Pandora’s rapid growth (18:40) and what he thinks of capital allocation and valuations today (23:20).
Product. Market. Team. Though a significant amount has changed in venture over the past two decades, the focus on these three variables has still remained largely the same when it comes to investing. In our eleventh episode I chatted with one of the most successful venture capitalists of the past two decades, Brad Jones, Founding Partner at Redpoint.
Brad co-founded Redpoint in 1999 after serving as a General Partner at Brentwood Venture Capital. Over the past 20 years, Brad has served on the boards of over 10 public companies and his team has invested in household names like Stripe, Twilio, Zendesk, Fortinet, Heroku and early on, Netflix.
Brad and I spoke for about an hour and covered a number of topics in this one; we talked about startups, the state of venture capital and where we’re headed. Some of my favorite moments included: why less companies going public is bad for retail investors and broader society (17:20), his observations on how starting and scaling a startup has changed over the past 15 years (21:44), what he thinks of the state of culture in the technology community today given the recent turmoil at Uber (25:46) and ideas for how local and national government can help startups (43:21).
High-growth companies can now start and scale anywhere, not just in a few coastal cities. This is the fundamental premise of Revolution Ventures, the $200M venture capital firm started by AOL, Inc. founder Steve Case. In our tenth episode, I chatted with David Golden, Managing Partner at Revolution.
David joined Revolution after 18 years with JPMorgan. During his tenure at JPM, David held a number of roles, including Vice Chairman and Director of JPMorgan’s global investment banking practice for Tech, Media & Telecom. Throughout his career, David has served on the boards of a number of successful companies, including Everyday Health, Barnes & Noble Education and Blackbaud.
Bessemer Venture Partners has long been regarded as one of the most successful and influential venture capital firms in Silicon Valley. The firm has invested in a number of winners over the years including: LinkedIn, Yelp, Blue Apron, Periscope, Twitch, Shopify, Twilio and others. In our ninth episode, it was fun to chat with Ed Colloton, Managing Partner and COO over at BVP. Ed has had a very successful career both in PE and VC; he served as COO of JP Morgan’s Private Equity arm before transitioning to Bessemer where he has been recognized on the annual Forbes Midas List as one of the top 100 venture capitalists globally.
Ed and I spoke about a number of topics in this one; namely, what’s the future of VC look like, why less companies are going public, and what makes Silicon Valley special. My favorite moments included: (1) his thoughts on PE vs. venture as an asset class (21:54), what the ramifications of less companies going public are for society and innovation (27:11) and given his experience in Silicon Valley how he thinks about clean sheeting a plan for a city to become an innovation hub (32:31).
There aren’t many companies in the history of the world that have had as much of a global impact as Facebook. That’s why in our eight episode, it was especially gratifying to chat with Chris Kelly, Former Chief Privacy Officer and Head of Public Policy at Facebook. Chris had the unique perspective of working at Facebook in the early days as one of the first 25 employees to being a key executive in a 1,000+ employee organization by the time he left in 2009.
We had a lot of fun in this one and Chris and I spoke about a whole host of topics: his experience at Facebook, thoughts more broadly on what’s going on in the tech community, and the intersection of government, tech and the future of innovation in the US. Some of my favorite moments included: (1) his reflections on what it was like working with Mark Zuckerberg and how to think about culture (16:20), (2) what he thinks the next wave is in tech and whether its IoT, AR or VR (26:10) and (3) how to think about managing the downsides of emerging technologies, namely fake news (30:30)
It’s no question that AI is going to have an extremely large impact on our society. Like “the cloud” five years back, today machine learning is starting to become a common household word. In our seventh episode, I had the chance to chat with Ben Alden, General Counsel of Betterment and we dove into all things disruptive innovation in the wealth management space. Betterment has raised over $200m and manages more than $7bn assets globally. It is one of the darling stories of fintech (having been previously referred to as the “Apple of Finance”) and has a number of exciting future products in store for a rapidly growing trillion dollar industry. Ben is a native of Cornell University and Stanford Law and practiced as a Litigator at Sullivan & Cromwell amongst other roles prior to serving as GC at Betterment.
In our sixth episode, I had the chance to chat with Chad Ho, Senior Vice President and General Counsel of Hulu. Chad’s had an interesting career in the entertainment space and has seen the highs (and lows) of multiple startups; he was employee #70 at MySpace and saw the website become the #1 most visited site on the internet and grow to 1,200 employees within a few years only to see it brought right back down to earth as Facebook came in and took over the space. Around that time he moved on and joined a then unknown and unnamed company as its General Counsel — fast forward a decade and that company has become Hulu, a global household name doing $1bn+ revenue annually.
In our fifth episode, I had the chance to chat with Andrew Yang, Founder and CEO of Venture for America, a fellowship program for enterprising recent college graduates to launch their careers as entrepreneurs and revitalize American cities. Andrew has accomplished a lot with VFA since founding it in the last 6 years and has been a tireless advocate for entrepreneurship. He’s spoken at length on the subject, appearing on CNN, CNBC, Time, and the Wall Street Journal. Andrew was named a Presidential Ambassador for Global Entrepreneurship by the White House and one of Fast Company’s 100 Most Creative People in Business for his work with Venture for America.
This conversation was a lot of fun; Andrew really humanized entrepreneurship and how to get comfortable with the uncomfortable. Some of my favorite moments included: (1) why entrepreneurship isn’t a magic trick (3:05), (2) how he sees entrepreneurship shaking out over the next decade (16:55), (3) the consciousness that has emerged from this election cycle (24:06), and finally (4) key takeaways for young professionals (40:01).
Check out Andrew’s awesome book “Smart People Should Build Things.”
In our fourth episode, Romeen had the chance to chat with Patrick Chung, Founder and General Partner at Xfund, a $50M seed stage venture fund based in Silicon Valley. Patrick is an incredibly sharp guy; he has had an impressive academic career — with three degrees from Harvard University (College, Law School, and Business School) and one from Oxford University — and professional career, having been a consultant at McKinsey, operator at venture backed Zefer, and General Partner both at NEA and xFund.
This conversation was fun and Patrick gave a lot of interesting insight. Some of my favorite moments included: (1) why he thinks liberal arts founders thrive and his fund is a bet on that (6:05), (2) how an influx of capital affects seed stage investing (14:13), (3) why managing uncertainty will be a key strategy in 2017 (20:24), and finally (4) three key takeaways for young professionals (35:22).
In our third episode of Square One, Romeen had the chance to chat with David Hornik, General Partner at August Capital. David has a reputation in venture as one of the nicest and sharpest investors out there. He received Deloitte’s 2013 Venture Capitalist of the Year award and has been honored by Forbes Magazine as a member of its Midas List of top Venture Capitalists.
This conversation was fun and David gave a lot of interesting insight. Some of our favorite moments included: (1) what he thinks of the current state of venture (11:05), (2) his adamant belief that we are not in a bubble, though things are overheated and overfunded (17:05), (3) the importance of making others successful and being generous (24:01), and (4) focusing on a happy life, not a successful career (30:10).
David colored a lot of these insights via personal anecdotes of times with Jerry Yang, DJ Patil, Dick Costolo, Paul Graham, Reid Hoffman, Travis Kalanick and others.
In the second episode of Square One, Alex had the opportunity to chat with Andrew Feldstein, the Co-Founder, CEO and Co-CIO of BlueMountain Capital, as well as the Chair of the Firm’s Management Committee and a member of the Investment and Risk Committees. After earning a BA from Georgetown, Andrew spent two years at Bain & Co., then enrolled at Harvard Law School for a JD. From Harvard, Andrew joined Sullivan & Cromwell as a tax attorney and, soon after, transitioned to J.P. Morgan. Over the course of a decade at J.P. Morgan, Andrew was a Managing Director and served as Head of Structured Credit; Head of High Yield Sales, Trading and Research; and Head of Global Credit Portfolio. In 2003, Andrew launched BlueMountain Capital, today a diversified alternative asset manager with over $20bn under management.
Alex and Andrew discussed his early career, how he decided to start BlueMountain, and some of the key lessons he picked up along the way. Andrew had many interesting insights, a few of which include: (1) key tail/headwinds for investors today (10:55), (2) the application of constitutional law and civil procedure to running a business (18:15), and (3) the importance of trying to learn something interesting from every interaction (25:44).
In the inaugural episode of Square One, Romeen had the chance to chat with Jim Koch, the billionaire Founder and Chairman of Boston Beer Company (maker of Sam Adams). Jim is an incredibly sharp operator and is revered as the founding father of the American craft brewery movement. Born into a middle class family in Cincinnati, Ohio, he spent a formative decade of his life in Cambridge, earning a BA, JD, and MBA from Harvard. After 6 years as a Consultant at the Boston Consulting Group, Jim took a risk, quit his job and started selling Sam Adams. Today Boston Beer Company has annual revenues of ~$1 billion and sells more than 50 types of beer all over the world.
Romeen and Jim discussed his early life, how he made the decision to start Boston Beer Company, and the key lessons he picked up across his career. Jim had many interesting insights, but a few that resonated most were: (1) get out of your echo chamber when making decisions (8:05), (2) laser focus your early career on developing skills (20:36), and (3) always be selling (24:44).