Introducing: The Only Thing That Matters: Getting Your Startup to Product-Market Fit on Chicago Founders TV

Pat Ryan
Cooler By The Lake
Published in
3 min readMar 22, 2017

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As I’ve moved from a two-time B2B SAAS entrepreneur into my role as chairman of Chicago Ventures, the number of startups that I get exposed to has increased exponentially. What has amazed me most, though, is the inspiring founders that I’ve met along the way, and the interesting visions that I’ve come to understand throughout this journey.

Yet as I watch people navigate the challenges of early-stage startup life I can’t help but be reminded of the wisdom of entrepreneur-turned-VC Marc Andreessen’s legendary blog post, where he touts product-market fit as “the only thing that matters.”

The experiences of these talented and committed entrepreneurs has really reinforced for me that getting your startup to product-market fit is the most critical challenge that every founder faces and truly the “only thing that matters.” With that in mind, I started to mine the archives of our Founders’ Stories series at 1871 and the wisdom of the hall-of-fame-level entrepreneurs that I’ve interviewed over the last five years.

I realized that what I found was so profound that it would not only be useful to founders of Chicago Ventures companies, but could be game-changing for any founder out there.

With that in mind, I’m pleased to launch a brand-new 12-episode series on Chicago Founders’ TV. True to Marc’s words, the series is called “The Only Thing That Matters: Getting Your Startup to Product-Market Fit”.

In it, we dive deeper into our Founders’ Stories interviews, and share some of their most special insights on the challenges and successes they faced on the way to finding true product-market fit in their business.

In our very first episode, I had the pleasure of sitting down with Morningstar founder Joe Mansueto, a powerful entrepreneur who grew the investment management firm from a budding business based in his Chicago apartment to a $3.13B market cap today. You can watch that first episode here:

Here’s who else you can expect in upcoming episodes:

● Bonobos and Trunk Club founder Brian Spaly who sold Trunk Club for $350M to Nordstrom

● Fintech entrepreneur Al Goldstein, whose most recent company, Avant, has raised over $1.4B in funding

● Fieldglass founder Jai Shekhawat, who sold his company to SAP for over $1B

● Bazaarvoice (NASDAQ:BV) entrepreneur Brett Hurt, who also founded CoreMetrics and sold it to IBM, and just recently launched data.world

● Basecamp/37Signals founder, CEO and thought leader Jason Fried

● kCura founder Andrew Sieja, who landed a $125M investment from ICONIQ Capital

● Braintree founder Bryan Johnson who sold his company to PayPal for $800M

● Serial entrepreneur Sam Yagan, who founded SparkNotes, eDonkey, OkCupid, and Excelerate Labs

● GrubHub co-founder and CEO Matt Maloney who grew the online food ordering app to a market cap of $3.28B

● Raise Marketplace founder George Bousis, who has built the leading online marketplace for gift cards, backed by NEA and Bessemer Venture Partners

● Serial finance and music entrepreneur David Kalt, who founded OptionsXpress (sold to Charles Schwab for $1B) and online instrument marketplace Reverb.com

Don’t forget to hit “subscribe” at the top of this site for more updates and find us on YouTube for bonus content!

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