Square One: Conversations with the Best in Business

There’s a fundamental problem in the workforce today - 43% of skilled women exit the workforce after having children. The economic loss we face from this input is dramatic. We know anecdotally and scientifically that gender diversity (amongst other forms of diversity) materially improves the bottom line. Though that may be the case, we’re not doing a great job to re-engage this workforce. This is why this week’s guest - Allison Robinson - built The Mom Project. The Mom Project is a digital talent marketplace and community that connects professionally accomplished women with world class companies. I think of The Mom Project as the best of a staffing company, best of a job board, wrapped in a differentiated community, all empowered by best in class technology. Allison has raised $10M+ from some of the best investors in the world, has Serena Williams as a key advisor and is facilitating opportunity for over 250,000 moms on her platform today.

There's one document that every business lives on - contracts. But the contract management space and legal industry more broadly has been a historical laggard of innovation and technology adoption. Enter Ironclad. Ironclad simply put is a startup that makes it easier for legal teams to manage their contract workflow. This isn't a small problem by any stretch - the company has raised over $80M from Sequoia, Accel, Emergence Capital and Y-Combinator Continuity to fundamentally change the interaction model between businesses and their contracts. I chatted with Jason Boehmig, Founder and CEO at Ironclad on how he's building one of the most interesting companies in the legal industry today. 

All disruptive technologies start selling first to early adopters in the market. As the customer base and market matures, successful disruptive technologies evolve adding sophistication that larger customers need at scale. Intercom is a perfect example of this - first selling to companies in their Y-Combinator batch, today Intercom has raised over $250M and counts over 30,000 organizations as customers. Intercom is one of the fastest growing SaaS startups of all time and with good reason - the team had a fundamental perspective on how to make a Messenger product for the enterprise and has translated this vision into a robust and holistic customer communication platform that services the full lifecycle for internet businesses - from acquisition to engagement and engagement to retention. I chatted with Des Traynor, Co-Founder and Chief Strategy Officer at Intercom on all things Intercom and leading a high growth startup.

Historically access to celebrities was far removed and impersonal - glossy center magazines and billboards, fans were unable to interact with their favorite stars. Social media has fundamentally changed the interaction model; talent has increased its ability to leverage fandom into commercial opportunity and fans have come to expect more and more personalization and engagement. Cameo has fundamentally changed the game. Started just 3 years ago, the company has raised $56M to facilitate personalized messages from celebrities to fans. In this episode, I chatted with Steven Galanis Founder and CEO of Cameo and we touched on a number of topics including: (1) how the internet has changed engagement, (2) the network effects of building a fast growing marketplace business, (3) why Cameo is best positioned to compete against Instagram, Snapchat and YouTube, (4) the responsibilities that come with a fast growing, B2C organization and (5) ancillary use cases that can be created of Cameo at scale.

This week's episode took a different turn than our normal programming. COVID-19 has ravaged every sector of the economy; while BigTech has stayed relatively flat and certain areas have seen unprecedented demand, the vast majority of the world is working through an excruciatingly tough,  once-in-a-century type event. This week I chatted with Hunter Walk, Co-Founder and Managing Partner at Homebrew Ventures. Hunter and team have $200M in assets under management and have invested in some of the biggest generational winners of our time including Plaid, Bowery Farming, Chime, BuildingConnected and Cruise amongst others.  We talked all things tech and venture capital during this incredibly trying time. 

Autonomous vehicles have been all the buzz over the last few years. Not to be outdone, Amazon has quietly been applying this same technology to checkout. In 2018, Amazon announced "Go" - a grocery story with frictionless checkout. Since then, Amazon has been building and launching stores across the country. While promising from a technology perspective, retailers have fears of being locked in the Amazon ecosystem; we saw the same net effect play out with Instacart. As Amazon acquired Whole Foods retailers turned to Instacart to offset Amazon's delivery capability.  Enter Standard Cognition (SC). SC is building autonomous checkout on the backs of ~$100M raised over the past 2 years. SC is focused exclusively on AI-powered checkout: SC enables autonomous checkout for brick and mortar retailers with an AI-powered computer vision platform.  In this episode, I chatted with Jordan Fisher (Founder/CEO of SC) and we touched on a number of topics, including: (1) the future of retail analytics and in-store experience, (2) the challenges of selling technology in a low margin industry, (3) how his technology differs from Amazon/why Amazon didn't create Go in stealth and take out all of the oxygen out of the room, (4) the implications of autonomous technology for global privacy standards and job creation/destruction and (6) ancillary possibilities that could be created as a byproduct of the SC technology at scale. 

No code is a trend that has powered much of the internet since the days of Dreamweaver. However, in 2020, "no code" is making a come back at a stronger pace than ever before. The world operates on code, but only every 1 in 400 understand it; imagine if only every 1 in 400 people could write - the world would be an incredibly different place. This week we were joined by Vlad Magdalin, Founder and CEO of Webflow - one of the pioneers of the "no code" movement. Vlad recently raised $72M from Accel Partners to scale his vision into reality. We touched on a number of topics in this conversation - dealing with rejection in the early days, the irrationality to keep going when things looked bleak, how he grew to $20M ARR with limited outside financing, why he raised a monster round from Accel and why he believes this is the inflection point for "no code." At the end of the discussion, we finished out by talking about gratitude - Vlad came to the US as a refugee from Russia at 9; gratitude has shaped his outlook on privilege and the real priorities in life. This conversation was a ton of fun - a lot of the folks we have on the podcast are winning in an objectively massive way. Vlad is a genuinely good guy and it's awesome to see him specifically win. 

Workplace communication predictions over the last 5 years has been dominated by the rise of chat apps like Slack and email ostensibly becoming eliminated. Yet email lives and thrives today - according to Radicati, nearly 300 billion emails are sent and received every day. The conversation around email - though such an important driver of workplace communication - has been stagnant. Enter Superhuman, the next generation email platform. Superhuman has gotten the attention of Silicon Valley’s most prominent and the levels of virality in this product mirror Slack and Dropbox in the early days. It was a pleasure to have Rahul Vohra, Founder and CEO this week; Rahul has raised $40M+ and is using that resource base to drive his uniquely quantitative perspective on evaluating product market fit - a topic we spent much of the discussion on. He also shared his perspective as to what holds for the future of email, why the enterprise will pay for products that have historically been free, and why he and his team are so well placed to compete with free from the 800 pound gorilla of email, Google.

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