Building an AI EdTech Company: College Guidance Network CEO Jon Carson (Part 1)

Jon has identified a gigantic hole in high school college counseling and is plugging it with AI.
You have read interviews with the entrepreneurs behind Empowerly and Prepory, companies going after the same problem, but with more manual solutions. College Guidance Network is doing so with AI.

Bootstrapping a High Growth Cyber Security Venture with a Paycheck: Christian Geyer, CEO of ACTFORE (Part 1)

Christian convinced the Board of his employer to let him incubate a Cyber Security startup idea as a division of the company with an express intent of spinning it off.

Now, the company has been spun out, doing almost $20M in bootstrapped annual revenue, and may soon find a lucrative Exit. This is a phenomenal story for entrepreneurs considering the Bootstrapping with a Paycheck route.

The Startup Velocity Question: Positioning Drives Exit

There is a commonly held misconception among operators who do not understand positioning: We don’t want to invest in Positioning. We will be selling the company.

The Startup Velocity Question: Market Shifts Derail Companies

Let’s take a most obvious example: BPO companies offering large numbers of customer support agents to other businesses.

Enter AI.

Bringing a Generative AI Product to Market: RJ Talyor, Founder CEO, Backstroke and Pattern89 (Part 7)

Sramana Mitra: Now, what did you decide this time around in enterprise versus SME? Where did you position? And did you start with a good, solid positioning and commitment?

RJ Talyor: We’re going right after the mid-market. We’re looking at businesses or retailers, specifically with 100-1,000 employees. We’re looking for people who send two to three emails every week, and that means that they care about email. They have a team of two to four people who are interested in getting better, and they likely have a set of vendors that we understand, and are willing to move quickly. That’s pretty much what we’re interested in.

Best of Bootstrapping: Bootstrapped to Exit, Bootstrapped Again, then Raised VC Money

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. 

Stephanie Leffler, CEO of OneSpace, had bootstrapped her first company to $20 million in revenue from St. Louis when we spoke in 2016. Her second company, also from St. Louis, was venture-funded and had crossed $10 million in revenue. Awesome entrepreneur, inspiring woman! You can also listen to our conversation as a podcast here.

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

Stephanie Leffler: I am from Northern Virginia in Fairfax. I was actually born and raised there. Ultimately, I went to school at Washington and Lee University. I found my way to St. Louis as part of my entrepreneurial journey. I’ve lived here ever since.

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Best of Bootstrapping: Bootstrapped to Over $20M and Exit

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. 

We’re big fans of bootstrapping to exit case studies. Imagine Easy Solutions’ Co-founder and Co-CEO Neal Taparia shares his wonderful journey. They scaled the business to over $20 million in revenue without investment and sold to Chegg in 2016.

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?

Neal Taparia: I was born in the suburbs of Chicago. My parents were immigrants from India. I’m first-generation in the United States. I did my undergraduate education in Chicago. After that, I settled down in New York where I’ve been ever since. 

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568th 1Mby1M Entrepreneurship Podcast with Abinash Saikia, EnCloudEn (Part 1)

Abinash Saikia, Co-founder of EnCloudEn and former 1Mby1M Premium member, has successfully bootstrapped his venture to an exit and discusses the process in great depth.

Sramana Mitra: Let’s start by introducing our audience to yourself as well as to the premise of EnCloudEn.

Abinash Saikia: I have had a pretty good education from IIT Chennai and, subsequently, an MBA from IIM Bangalore. I worked for a couple of years but the entrepreneurial bug was always there. I could not continue for much longer. I left my job and started a company called SmartBuildings. I was at that company for about three years. It was mostly an IoT-based energy conservation solution.