Inspired with Alexa von Tobel

Latest Episodes:

How to Measure Time by Impact with Jyoti Bansal of Harness and Traceable Mar 15, 2023

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Jyoti Bansal is a serial entrepreneur, through and through. In 2008, he first made the leap from startup engineer to CEO with AppDynamics, a company that was acquired by Cisco for $3.7 billion just under a decade later. After giving retirement a shot, he returned to the founder seat: he started software delivery unicorn Harness, cybersecurity platform Traceable, startup accelerator BIG Labs, and VC firm Unusual Ventures—and has more than 25 US patents under his name. Jyoti shares his simple formula for finding product-market fit, why ringing the Nasdaq closing bell was part of his Cisco negotiation, and how he's learned not to stress about things outside of his control.

How to Scale via Product-Led Growth with Eugenio Pace of Auth0 and Okta Mar 08, 2023

Show notes

Over his decade-plus at Microsoft, Eugenio Pace became an expert in cloud computing and identity management, co-authoring several books on the topic. His drive to solve the problem of identity management for fellow developers inspired him to start a company of his own, Auth0, in 2013. Over eight years, he scaled the company into a trusted global brand, leading to a 2021 acquisition by Okta in a $6.5 billion dollar deal. Today, Eugenio is the President of Customer Identity at Okta, serving Auth0's and Okta's combined customer base. Eugenio shares why they decided to offer parts of Auth0 for free, why he attributes his success to a CEO development program, and why he felt like it was the right moment to sell his company—even though Okta started courting him years prior.

How to Stay Emotionally Calibrated with Tim Chen of NerdWallet Mar 01, 2023

Show notes

In 2009, Tim Chen found himself laid off from his Wall Street job and was trying to figure out his next move. But a simple question from his sister about finding the right credit card turned into the core idea for NerdWallet, the company on a mission to give consumers clarity around all of life's financial decisions. NerdWallet started as a tool to help people shop for credit cards, but has scaled to serve over 19 million users. In 2021, Tim led NerdWallet through an IPO. Tim shares why they raised venture capital only after the company was profitable, why he loves the Jeff Bezos quote that very few decisions are irreversible, and how his parents instilled Tim's entrepreneurial drive.

How to Create a Design-Centric Platform with James Hirschfeld of Paperless Post Feb 22, 2023

Show notes

While a sophomore at Harvard, James Hirschfeld put lots of time into planning his 21st birthday party—but when it came time to figure out invitations, there was no option that spoke to him, between expensive stationery and clunky online tools. He started Paperless Post in 2009 along with his sister, Alexa, and has since reimagined the experience of sending and receiving invitations for over 175 million users. James shares why it was an uphill battle convincing investors that consumers wanted premium tools for digital communication, how they turned the business impact of the pandemic (the worst thing that could happen to a company centered on events) into an investment in the future, and why user trust and loyalty is sacred.

How to Build an Evidence-Based Business with George Fraser of Fivetran Feb 15, 2023

Show notes

In 2012, George Fraser teamed up with his lifelong friend, Taylor Brown, to build Fivetran. Their initial vision was completely different from what Fivetran is today: a fully managed automated data integration provider, valued at over $5 billion. But the two listened to customer conversations and realized that they could build a viable business around a singular pain point. Fivetran now serves thousands of customers and hundreds of leading brands across the globe. George shares how his PhD in Neurobiology impacts his style as a founder, why fear of failure is an underrated motivator, and why they got creative with a major acquisition in order to build a full-spectrum offering overnight.

Why Execution is More Powerful Than Ideas with Allon Bloch of K Health Feb 08, 2023

Show notes

Allon Bloch is no stranger to starting companies, but when he launched K Health, he was new to healthcare. Before K Health, he was the CEO of website publishing platform Wix and car retailer Vroom. But his father's health struggles inspired him to turn his focus to delivering high quality medicine at scale. He co-founded K Health in 2016 and has scaled the platform into the #1 downloaded app in the medical category, covering over 6 million people. Allon explains how K Health leveraged AI early on to teach a machine the language of medicine, why he believes it's a great time to be a healthcare entrepreneur, and why he attributes his success to the partnership of strong co-founding teams.

How to Be the Customer with Anthony Casalena of Squarespace Feb 01, 2023

Show notes

Nearly twenty years ago, Anthony Casalena was a student at the University of Maryland who wanted to build himself a website. Finding no easy platform in the market, he created his own. Today, Squarespace is an all-in-one website building and ecommerce platform used by more than 4.2 million people. Anthony worked as a team of one for the first few years, but now has over 1,800 employees and took Squarespace public in 2021. Anthony shares how he got his idea off the ground with a $30,000 investment in servers and Google AdWords, why it still feels surreal to see a Squarespace ad at the Super Bowl, and how running a public company is completely different than what he expected.

How to Deliver Real Value with Ara Mahdessian of ServiceTitan Dec 21, 2022

Show notes

Growing up, Ara saw firsthand how hard his father worked as a contractor running a trade business. When he met Vahe Kuzoyan, a fellow Armenian immigrant whose family worked in the trades, they saw an opportunity to help their own families work more efficiently and grow their businesses. Over time, word spread and they decided to go all in on building ServiceTitan. With a valuation over $9B, ServiceTitan helps thousands of customers in the trillion dollar trade industry. Ara shares how his dad wandering the aisles of Barnes & Noble kicked off his coding skills, why the two victories of B2B software are making customers money or saving them money, and how he and Vahe strive to cultivate a winning culture.

How to Operate with Velocity with Waseem Daher of Pilot Dec 14, 2022

Show notes

Co-founder dynamics can be notoriously challenging. But Waseem Daher and his co-founders, Jeff Arnold and Jessica McKellar, are now building their third business together. Their most recent company is Pilot, which they started in 2016 to solve a pain point they experienced as founders: how time-consuming it can be to manage company finances. Pilot is now the largest startup and SMB bookkeeper in the United States, serving over 1,900 clients. Waseem shares why speed is the most critical advantage for startups to leverage, how he learned to delegate in later stages, and why a founder's strongest ethical obligation is to their customers and team.

How to Build a Vertical Product with Andrew Bialecki of Klaviyo Dec 07, 2022

Show notes

What if brands were empowered to deliver personalized experiences online, just as well as they could do in a store? That's the idea that underpins Klaviyo, the leading customer and marketing automation platform. Andrew Bialecki cofounded Klaviyo in 2012 and now serves over 100,000 brands, helping them generate $28 billion in revenue for its customers in 2021 alone. Andrew shares why he bootstrapped the business until profitability, how early partnerships can be a key to efficient customer acquisition, and why he feels like he's only achieved 1% of Klaviyo's potential.

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