Best of Bootstrapping: Bootstrapped with Services to $10M and an Exit

Among the biases of the Venture Capital industry that need to be categorically ignored, Bootstrapping Using Services happens to be on the top of the list. Zimit Founder and co-CEO James Cramer shared yet another fantastic textbook case study when we spoke in 2021. Zimit was acquired by Workday in September 2021.

Sramana Mitra: Let’s start at the beginning of your journey. Where are you from? Where were you born and raised? What kind of background did you have?

James Cramer: I was born in Southern California. I grew up in a family that moved around a lot. My dad worked in the automotive industry, and so every few years we would change locations. That put me in Seattle, Southern California, the Carolinas, and then ultimately in Florida.

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Bootstrapping a New Age AI Services Venture: Anji Maram, CEO of CriticalRiver (Part 7)

Sramana Mitra: You said at the beginning of the interview that you were trying to make up for the margin gap in services companies with velocity. Did you succeed in doing that? In the ten years that you’ve been in business, did you succeed in growing at a very high velocity?

Colors: Zahara I

I’m publishing this series on LinkedIn called Colors to explore a topic that I care deeply about: the Renaissance Mind. I am just as passionate about entrepreneurship, technology, and business, as I am about art and culture. In this series, I will typically publish a piece of art – one of my paintings – and I request you to spend a minute or two deeply meditating on it. I urge you to watch your feelings, thoughts, reactions to the piece, and write what comes to you, what thoughts it triggers, in the dialog area. Let us see what stimulation this interaction yields. For today – Zahara I

Zahara I | Sramana Mitra, 2019 | Watercolor, Ink | 16  x 20, On Paper

Video FAQs

Bootstrapping a New Age AI Services Venture: Anji Maram, CEO of CriticalRiver (Part 6)

Sramana Mitra: A lot of enterprise conversational AI applications that you’re talking about are happening more on the customer end – customer service, sales, or customer relationship management. It’s not much on the finance end. So, you rightly point out that this is a more of an open area where you’re starting to see traction.

What is the business model of how you are going to market with your AI solutions? When you do this conversational AI or automation projects, how are you pricing it?

Colors: Illusion V

I’m publishing this series on LinkedIn called Colors to explore a topic that I care deeply about: the Renaissance Mind. I am just as passionate about entrepreneurship, technology, and business, as I am about art and culture. In this series, I will typically publish a piece of art – one of my paintings – and I request you to spend a minute or two deeply meditating on it. I urge you to watch your feelings, thoughts, reactions to the piece, and write what comes to you, what thoughts it triggers, in the dialog area. Let us see what stimulation this interaction yields. For today – Illusion V

Illusion V | Sramana Mitra, 2019 | Watercolor, Ink | 16  x 20, On Paper

April 3 – 679th 1Mby1M Mentoring Roundtable for Entrepreneurs

Entrepreneurs are invited to the 679th FREE online 1Mby1M Mentoring Roundtable on Thursday, April 3, 2025, at 8 a.m. PDT / 11 a.m. EDT / 5 p.m. CEST / 8:30 p.m. India IST.

If you are a serious entrepreneur, register to Pitch and sell your business idea. You’ll receive straightforward feedback, advice on next steps, and answers to any of your questions. Others can register to Attend to watch, learn, and interact through the online chat.

You can learn more here and REGISTER TO PITCH OR ATTEND HERE. Register and you will receive the recording by email, even if you are unable to attend. Please share with any entrepreneurs in your circle who may be

678th 1Mby1M Roundtable Recording

In case you missed it, you can listen to the recording of this roundtable here:

Roundtable Recap: March 27 – The Realities of Pre-Seed Funding

During this week’s roundtable, we had extensive discussions about the realities of pre-seed funding. If you’re in the market for such investment, please review.

Tesser Payments

As for the entrepreneur pitches, up first we had Geetha Panchapakesan from Mountain View, California pitch Tesser Payments, a concept-stage FinTech venture.

Water Current Power

Then we had Michael O’Malley from New Bedford, Massachusetts pitch a hydro-energy idea.

You can listen to the recording of this roundtable here:

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