Best of Bootstrapping: Bootstrapped with Services, Raised Money and Exited

John Stewart and his co-founder built MapAnything from Charlotte, North Carolina and Atlanta, Georgia. When we spoke in 2018, he had raised over $40 million in funding, proving that you can build sizable VC-funded SaaS businesses from anywhere. MapAnything was sold to Salesforce in May 2019.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where did you grow up? Give us some early story.

John Stewart: I’m from upstate New York. I’m from a middle class background. My mother was a stay-at-home mom. My father was in the construction business. He was an architect. I went to school in New England for Mechanical Engineering at Worcester Polytechnic Institute in western Massachusetts and graduated in 1997.

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Best of Bootstrapping: Bootstrapped to $45 Million from Chicago

RKON Technologies CEO Jeff Mullarkey had built a Managed Service Provider (MSP) business that I thought he could take to $500 million or a billion dollars in revenue when we spoke in 2015. Read on to learn why.

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

Jeff Mullarkey: I’m from the Chicago area. I grew up in a modest environment. I went to Illinois State University. I graduated with a Marketing degree with little clue of what I want. Right at this moment in time, personal computers had started to emerge. I frankly had never even used one. I stumbled into taking a job selling PCs. That’s how I got into the industry. It was a little bit by fluke. It was a very small industry at that time. This was 1986. That was how I got into IT.

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Building a New Age AI Services Company: Cognida CEO Feroze Mohammed (Part 1)

IT Services is going through a profound shift. Huge opportunity for more companies like Palantir to be built. This discussion parses the nuances of building such ventures. Needless to say, VC money is now going to flood into this model.

Best of Bootstrapping: Bootstrapped a Healthcare Tech Company to $100M

When we spoke in 2015, Edifecs Founder Sunny Singh had built a very interesting healthcare technology company, overcoming serious challenges. Inspiring story of a bootstrapped success.

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

Sunny Singh: Give or take, I’ve spent half my life in the US and half my life in India. I grew up in India and finished my undergraduate studies there. Then, I came to the US at the age of 23 to do a couple of Master’s programs. I did three jobs and then started Edifecs in 1996.

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Best of Bootstrapping: Bootstrapped to Exit, Raised Money and Exited Again

Wendy CEO Lance Neuhauser bootstrapped his first company to an exit. He venture funded his second company and exited after 10 years. He is about to launch his third. Read on, great story.

Sramana Mitra: All right, Lance, let’s start at the very beginning of your journey. Where are you from? Where were you born, raised? What kind of backgrounds? What brings us to the entrepreneurial journey?

Lance Newhauser: Thank you for having me here. I really appreciate the opportunity. Your mission is admirable, and I love that you’re helping companies grow across the world.

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Best of Bootstrapping: Three Co-founders Bootstrapped with a Paycheck

CEO Ganesh Shankar and his two co-founders have built Responsive with a very small amount of capital. They started by Bootstrapping with a Paycheck and are now at over $50 million in revenue. Excellent execution, much to learn on many issues.

Sramana Mitra: Ganesh, let’s start at the very beginning of your journey. Where are you from? Where were you born, raised? What kind of background?

Ganesh Shankar: I’m originally from Coimbatore, India, down south. My entire childhood and my studies – undergrad and postgrad – were all in Coimbatore, the place where I was born and raised. I come from a family of government employees. There’s a saying in our family: “Even if you get a quarter cent, it better be coming from the government.” This was instilled in us by my grandmother, a strong character in our family. My dad works in the agriculture department, and my dad’s brother is a retired army colonel.

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2025 Resolution: Bootstrap a Startup with a Paycheck to Mitigate Risk

Let us say you start your entrepreneurial journey in 2025.

The question of funding looms large.

If you want to raise funding, most likely you would need to quit your job and go full-time.

Investors generally don’t fund companies that are led by part-time founders.

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2025 Resolution: Find an Experienced Mentor to Make Your Startup Fundable

As a startup mentor, I always think about how I can make the most impact.

These days, everyone claims to be a startup mentor. Whether they have ever done a startup or raised money, they are ready to give advice on how to raise money.

Most of the advice you get this way is blind leading the blind.

What constitutes good startup mentoring?

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