Inspired with Alexa von Tobel

What does it take to build the fastest-growing insurance brokerage in industry history? According to Greg Williams, it’s all about thinking three to four years ahead. When he cofounded Acrisure in 2005, he initially questioned the need for another insurance broker. Yet, by bringing his vision of the future into the day-to-day, Acrisure is now the sixth-largest insurance broker globally and the largest independent real estate services company in America. By providing customers with intelligence-driven financial services solutions, Acrisure combines the best of human capabilities with the best of technological capabilities, and is valued at more than $20B. Greg shares why highly successful people think differently, why he’s bullish on proprietary chatbots, and why he focuses heavily on vision and culture.

Grant LaFontaine, co-founder of Whatnot, shares insights on starting a customer-centric marketplace, niche community building with Funko Pop collectors, the importance of creativity in consumer startups, and why authenticity matters to today's shoppers.

In 1976, Jim McCann had spent a decade working in a group home for boys and was bartending on the side. A customer at the bar gave him a tip that there was an opportunity to buy a flower shop for $10,000. Jim took the leap and turned that single flower shop on Manhattan's East Side into a billion-dollar omni-channel retailer. He grew store by store, turning on a franchise model, expanding into new gifting categories (from The Popcorn Factory to Harry & David). Through it all, Jim had a knack for adopting new technologies ahead of other retailers. Jim shares where the company's iconic name comes from, how he positioned the company to become the first merchant of any kind on AOL, and why the best way to solve a problem is with a pen and a pad of paper.

Capital One is such an iconic brand that it is hard to imagine a time before it. But when Nigel Morris co-founded the business in 1994, it was wildly innovative—from the products it introduced to the market (like secured credit cards) to a data-driven approach to customer segmentation to an emphasis on team culture. Today, Capital One is one of the largest retail banks in the United States, serving more than 100 million customers across a diverse set of businesses. Nigel's career didn't stop there: he went on to start QED Investors, a fintech venture capital platform that has invested in companies like Credit Karma, Nubank, and Klarna. Nigel shares why Capital One's early success came down to rapid execution, why restlessness is a positive trait for founders, and how one interesting use case of AI is powering one-to-one marketing.

Harley Finkelstein first encountered Shopify as a user. Back in 2006, while in law school, he was one of the first merchants to use the platform. He joined the company in 2010 and now serves as President, helping to scale Shopify to millions of daily active users across 175 countries driving $444B in global economic activity. Today, Shopify is the all-in-one commerce platform to start, run, and grow a business—and is second only to Amazon as the largest online retailer in the US. Harley shares why the future of e-commerce is just the future of commerce, why his favorite motto is "how you do anything is how you do everything," and how being a power extrovert has made him a stronger leader.

Approaching a new industry as an outsider and as a team of one would be daunting for most founders. But Chen Amit, Founder and CEO of Tipalti, was a repeat entrepreneur building in a new arena. In the past 13 years, he has scaled Tipalti— a finance automation suite focusing on global payments and accounts payable—into one of the most highly valued privately-held fintech companies in the globe. With a valuation of $8.3B, Tipalti processes over $43B in payments annually. Chen shares why signing his third customer was his biggest signal of product-market fit, what playing poker taught him about taking calculated risks, and why he relearns his job every eighteen months.

Over the past 13 years, Warby Parker has become synonymous with offering stylish eyewear at revolutionary prices. The company was born back at Wharton in 2010, when a group of classmates—including co-CEO Neil Blumenthal, came together around an idea they couldn't get out of their heads. Since then, Warby Parker has grown to over 200 brick and mortar locations and went public in 2021. They've also hit a giant milestone: distributing 15 million pairs of glasses globally through their Buy a Pair, Give a Pair program, helping people get the glasses they need to learn, work, and achieve better economic outcomes. Neil shares how it took them six months and over 2,000 names to settle on Warby Parker, why getting pricing right was key to their early success, and why empathy is key to business-building. 

The company’s director of finance explains how her job goes well beyond accounting. Tina Hetzer, director of finance at Pink Lily, is one of the rising financial stars who are helping to bring their businesses to the next level. She built Pink Lily’s finance team from scratch and has helped the company become one of the fastest-growing retailers in the country. In this podcast, part of the SAP-sponsored Growth Agents series, Hetzer discusses the cash-flow challenges unique to fashion retailers and explains how working at a smaller, founder-run company can fuel greater collaboration across the organization.  

In 2014, as an engineer at a delivery startup, Daniel Yanisse identified an opportunity to improve a part of the HR tech world that was known to be high on friction. He co-founded Checkr to leverage technology to transform the world of background checks. Today, Checkr is a leading HR tech company that processes over 30 million background checks annually—and has earned a valuation of $5B. Daniel shares why the company is committed to Fair Chance Hiring, how Checkr grew alongside the on-demand economy companies it first served (like Instacart and Uber), and why being new to the industry was an advantage.

Duolingo’s freemium subscription model, beloved brand and strategic investments have allowed it to execute its educational mission and become a cultural touchstone. Matthew Skaruppa, CFO of Duolingo, is one of the rising financial stars who are helping to bring their businesses to the next level. Since he joined the company in 2020, Duolingo has grown its base of monthly active users by more than 80%. Each month, 75 million users hone their language skills on the Duolingo app. In this podcast, part of the SAP-sponsored Growth Agents series, Skaruppa discusses how his analytical background has allowed to him to be a more strategy-oriented CFO. For him, that has meant balancing big aspirations and finite resources, and turning the uncertainties of tomorrow into action today.