Best of Bootstrapping: VC-Funded Venture After Bootstrapping to Exit

A very effective way to dance the entrepreneurial Waltz is to do a bootstrapped company first, sell it, and then do another venture with a more ambitious agenda. From 2021, Jeremy Swift’s journey as Co-founder and CEO of Cordial is a great case study of this method.

Sramana Mitra: Let’s go to the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Jeremy Swift: I was born in Beaverton, Oregon. Most people know about Beaverton because of Nike. It’s a small suburb outside of Portland. I grew up in what I would consider a small middle class family. Both my parents were a rare breed and especially different from the path that I’ve taken in my life. The first job they got out of college is the same job that they retired with 40 plus years later.

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The Accelerator Conundrum: The Follow-on Funding Fantasy

The Accelerator Conundrum is a multipart series that challenges the prevailing wisdom of the tech startup ecosystem that entrepreneurs should Blitzscale out of the gate. Written by Sramana Mitra, the Founder and CEO of One Million by One Million (1Mby1M), the world’s first global virtual accelerator, it emphatically argues that a better strategy is to Bootstrap First, Raise Money Later, focus on customers, revenues and profits. 1Mby1M’s mission is to help a Million entrepreneurs reach a million dollars in annual revenue and beyond. Sramana’s Digital Mind AI Mentor virtually mentors entrepreneurs around the world in 57 languages. Try it out!

One of the most potent carrots dangled by accelerators, designed to lure in hopeful founders, is the implicit (and often explicit) promise of “follow-on funding.” 

The Accelerator Conundrum: The Premature Blitzscaling Pressure

The Accelerator Conundrum is a multipart series that challenges the prevailing wisdom of the tech startup ecosystem that entrepreneurs should Blitzscale out of the gate. Written by Sramana Mitra, the Founder and CEO of One Million by One Million (1Mby1M), the world’s first global virtual accelerator, it emphatically argues that a better strategy is to Bootstrap First, Raise Money Later, focus on customers, revenues and profits. 1Mby1M’s mission is to help a Million entrepreneurs reach a million dollars in annual revenue and beyond. Sramana’s Digital Mind AI Mentor virtually mentors entrepreneurs around the world in 57 languages. Try it out!

One of the most insidious pressures exerted by the typical 3-month accelerator model is the relentless push for premature blitzscaling. 

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The Accelerator Conundrum: The Herd Mentality and Groupthink Trap

The Accelerator Conundrum is a multipart series that challenges the prevailing wisdom of the tech startup ecosystem that entrepreneurs should Blitzscale out of the gate. Written by Sramana Mitra, the Founder and CEO of One Million by One Million (1Mby1M), the world’s first global virtual accelerator, it emphatically argues that a better strategy is to Bootstrap First, Raise Money Later, focus on customers, revenues and profits. 1Mby1M’s mission is to help a Million entrepreneurs reach a million dollars in annual revenue and beyond. Sramana’s Digital Mind AI Mentor virtually mentors entrepreneurs around the world in 57 languages. Try it out!

When you gather a cohort of startups, put them through the same program, expose them to the same “mentors,” and push them towards the same Demo Day objective, you inevitably foster a dangerous phenomenon: the herd mentality and groupthink trap. 

What Makes Your Startup Hard to Copy

AI is making it easy to build ultralight startups. AI is also making it easy for copycats to flood the market with competing products. Investors HATE a market full of copycats. If you are looking to raise funding, you have to be able to establish a defensibility thesis.

By and large, if you are building something that plugs some short term technology gap in a larger AI platform, that is not a defensible play.

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The Accelerator Conundrum: The Demo Day Delusion – A Launching Pad or a Showcase for Performative Entrepreneurship?

The Accelerator Conundrum is a multipart series that challenges the prevailing wisdom of the tech startup ecosystem that entrepreneurs should Blitzscale out of the gate. Written by Sramana Mitra, the Founder and CEO of One Million by One Million (1Mby1M), the world’s first global virtual accelerator, it emphatically argues that a better strategy is to Bootstrap First, Raise Money Later, focus on customers, revenues and profits. 1Mby1M’s mission is to help a Million entrepreneurs reach a million dollars in annual revenue and beyond. Sramana’s Digital Mind AI Mentor virtually mentors entrepreneurs around the world in 57 languages. Try it out!

Ah, Demo Day. The grand finale. The culmination of the 3-month sprint. 

It’s presented as the ultimate launching pad, your moment in the spotlight to capture the attention of investors, media, and potential partners, securing that coveted follow-on funding. 

The Accelerator Conundrum: The Mentor Mismatch

The Accelerator Conundrum is a multipart series that challenges the prevailing wisdom of the tech startup ecosystem that entrepreneurs should Blitzscale out of the gate. Written by Sramana Mitra, the Founder and CEO of One Million by One Million (1Mby1M), the world’s first global virtual accelerator, it emphatically argues that a better strategy is to Bootstrap First, Raise Money Later, focus on customers, revenues and profits. 1Mby1M’s mission is to help a Million entrepreneurs reach a million dollars in annual revenue and beyond. Sramana’s Digital Mind AI Mentor virtually mentors entrepreneurs around the world in 57 languages. Try it out!

Let’s address another glittering promise that often turns to dust: the “mentor network.” 

Every accelerator boasts an impressive roster of advisors, entrepreneurs-in-residence, and industry veterans, all touted as eager guides ready to share their wisdom. 

The reality, however, is frequently a chaotic mentor carousel, marked by superficial interactions and a profound lack of genuine, consistent engagement.

The Accelerator Conundrum: The One-Size-Fits-None Fallacy

The Accelerator Conundrum is a multipart series that challenges the prevailing wisdom of the tech startup ecosystem that entrepreneurs should Blitzscale out of the gate. Written by Sramana Mitra, the Founder and CEO of One Million by One Million (1Mby1M), the world’s first global virtual accelerator, it emphatically argues that a better strategy is to Bootstrap First, Raise Money Later, focus on customers, revenues and profits. 1Mby1M’s mission is to help a Million entrepreneurs reach a million dollars in annual revenue and beyond. Sramana’s Digital Mind AI Mentor virtually mentors entrepreneurs around the world in 57 languages. Try it out!

One of the most glaring deficiencies of the traditional 3-month accelerator model is its inherent one-size-fits-none approach. 

These programs operate on a batch system, putting dozens of diverse startups, across myriad industries and stages, through the exact same motions.