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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Are You Looking for a Startup Idea?

Are you looking for a startup Idea? Let me give you some notes on my Ideation Methodology.

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The Accelerator Conundrum: The Equity Drain – A High Price for Hype

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!

Now, let’s dive into the core financial fallacy of the 3-month accelerator model: the equity drain. We’ve touched on it, but it warrants a dedicated, unflinching look. 

You are giving away 5% to 10% – sometimes even more – of your company, your blood, sweat, and tears, for what? For a fixed-term program, a modest cash infusion, and a network that often proves to be more superficial than substantial. A high price for what amounts to some basic hand-holding and a lot of hype.

Best of Bootstrapping: An AI Startup Bootstrapped Using Services

Co-founder Nitesh Chawla bootstrapped Aunalytics while keeping his academic job at Notre Dame. This is our conversation from 2021.

Sramana Mitra: Let’s start at the very beginning of your story. Where are you from? Where you born, raised, and in what kind of background?

Nitesh Chawla: I’m from New Delhi although I was born in Calcutta. I did my schooling from Delhi Public School. Then I did my engineering from Pune. Then I came to the United States in 1993 right after finishing my undergrad. I went to grad school in South Florida. I got my PhD in Computer Science with a focus on Machine Learning and Data Science.

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Bootstrapping in the Age of AI

The Age of AI is also the golden age of Bootstrapping. And it is the golden age of Solo Entrepreneurs. With AI, you can build a lot in an ultralight mode and get VCs salivating. The key is Positioning. Let’s discuss the nuances.

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We Like Bootstrapping to Exit

This week, we’re discussing how the Age of AI is also the golden age of Bootstrapping, and also of Solo Entrepreneurship. Yes, you CAN and SHOULD bootstrap with a Paycheck. Yes, you CAN and SHOULD bootstrap to an Exit.

Are you trying to do a startup as a SOLO entrepreneur? Your time has come.

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Best of Bootstrapping: Founder Bootstrapped to $10M Using Services

Founder Sameer Maggon discussed bootstrapping SearchStax to $10 million using services with me in 2021. Excellently navigated journey!

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

Sameer Maggon: I grew up in Delhi. I did my engineering in Computer Science from Pune. Then I came back to my hometown to work for a document management company. Then I decided to learn more. I came to USC in Los Angeles and did my Masters in Computer Science. Since then, I’ve been in LA and worked in a variety of startups and larger companies in the greater Los Angeles area. 

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Grow Your Startup With a Paycheck

Are you still employed but dreaming of starting a company? I’m going to give you some contrarian advice: Do NOT quit your job. In 1Mby1M, we support entrepreneurs Bootstrapping with a Paycheck. There is no good reason to quit your job before validating your startup idea.

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