Best of Bootstrapping: Bootstrapped a $7M Company in Houston

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

My conversation from 2014 with Gaurav Khandelwal, CEO of ChaiOne, became an interesting strategy discussion about a company doing substantial revenue based on services, had productized a piece of its services business that was also generating over a million in revenue.

Sramana: Gaurav, let’s go to the beginning of your story. Where were you born? What kind of background were you raised in?

Gaurav Khandelwal: I was born in Kolkata, India. I came to the US for my undergrad. I grew up in a large city and I really wanted to experience something different, so I applied and went to school in a very small town in northern Indiana that was in an Amish community called Goshen College. Different universities come through India and interview students and applicants. That gives students a chance to meet with deans and hear about the schools. I met with several of them and this particular school was very interesting. They had a program that required every single student to spend a semester abroad to graduate. I had never heard of that before. I thought it was fantastic to know that every single student at that school had spent a semester in Indonesia, China, or some other country.

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From Developer to Cyber Security Entrepreneur with $10M Revenue and $18M Funding: LoginRadius CEO Deepak Gupta (Part 4)

Sramana Mitra: What were the components of the full authentication?

Deepak Gupta: We did a user name and password with social login. We were managing the full login and registration. Pretty much the whole element of login, registration, forgot password, and user activation.

Sramana Mitra: Were you still just within the Drupal ecosystem?

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Best of Bootstrapping: Raised Series A with $10M in the Bank

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

Dean A. Stoecker is Executive Chairman and founding partner of Alteryx, a leading software developer and a pioneer of agile business intelligence technology with analytics. We had this conversation in 2012 when Dean was CEO.

Sramana: Dean, let’s start at the beginning of your personal story. What is the context for your entrepreneurial journey? Where are you from?

Dean Stoecker: I grew up in a family business in Colorado. I would sit around the table every day and hear about the trials and excitements of owning a business. I went to school at the University of Colorado. I had the opportunity to travel the world through a program called Semester at Sea. That was where I got the idea that I wanted to have my own business. After I graduated, I moved to California and got involved in the information business.

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From Developer to Cyber Security Entrepreneur with $10M Revenue and $18M Funding: LoginRadius CEO Deepak Gupta (Part 3)

Sramana Mitra: In what timeframe did you zero in on the pricing model?

Deepak Gupta: We did experiments on pricing. After 9 to 12 months, we got to a decent pricing model.

Sramana Mitra: Can you talk about those experiments? What was working and not working?

Best of Bootstrapping: Bootstrapped Using a Paycheck to Exit

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Bootstrapping using a paycheck is still a real trend. Here’s the case study of Axosoft shared by Founder Hamid Shojaee in 2014. The company was purchased in 2020 by Resurgens Technology Partners.

Sramana Mitra: Hamid, tell us a bit about yourself. Where were you born and raised and in what kind of background?

Hamid Shojaee: I was born and raised in Iran. I was 10 years old when we moved to the United States.

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From Developer to Cyber Security Entrepreneur with $10M Revenue and $18M Funding: LoginRadius CEO Deepak Gupta (Part 2)

Sramana Mitra: What did you get done in those few months when you still had the job?

Deepak Gupta: At the beginning, there was a little hesitation whether the product was going to work. As soon as we launched, we started getting customers. Customers started asking questions. In those few months, I saw that there is a big need for this product.

Best of Bootstrapping: Bootstrapping a Big Data Company Using Services to Exit

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

We maintain that one of the best ways to identify complex problems worth solving inside enterprises is by offering services to them, thereby gaining exposure to the domain. DataSong is yet another case in point. After I spoke with Founder John Wallace, DataSong was acquired by MarketShare in 2015.

Sramana Mitra: Let’s start at the beginning. Where are you from? What kind of a backstory leads up to the entrepreneurial story?

John Wallace: I grew up in the South from a pretty modest background.

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