Best of Bootstrapping: Bootstrapped Journey of a Child Entrepreneur in India

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

Varun Shoor is the Founder of Kayako, a company offering advanced helpdesk management software. When we spoke in 2014, Varun was steering the overall direction of the company and as customer experience fanatic and lead product architect, taking an active role in the design and development of Kayako. One of Varun’s greatest passions is design. Applying modern, consumer-like design to stuffy business helpdesk software was Varun’s brainchild, and with it he founded Kayako in 2001.

Sramana: Varun, let’s start with your personal story. Where are you from? What is the backstory to Kayako?

Varun Shoor: I was born in Jalandhar, a city in Punjab. I have had no formal education. I started Kayako when I was 17. My family background is industrial by nature. My father is into manufacturing, primary tools such as hammers.

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Roundtable Recap: May 13 – A Solo Entrepreneur Case Study

During this week’s roundtable, we had as our guest Shane Neman, Founder of EZ Texting and JoonBug.com, Principal at Neman Ventures. Shane has bootstrapped two companies as a solo entrepreneur, found successful exits for both, and is now an investor. Needless to say, he has no bias against solo entrepreneurs.

You can listen to the recording of this roundtable here:

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Best of Bootstrapping: TextMe Founders Bootstrapped an App to $10M

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

This is a wonderful story of a self-financed company that built itself up to $10 million in profitable revenue. Led by Christophe Bach, an experienced and successful serial entrepreneur, this is a text-book case study of effective bootstrapping.

Sramana: Christophe, to start, tell me your back story. Where are you from, where were you born?

Christophe: I am the Co-Founder and Co-CEO of TextMe and prior to TextMe, I co-founded three companies in Europe. I was born and raised in Paris, France. I have been living between Paris and San Francisco for the last 15 years.

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Best of Bootstrapping: How An Entrepreneur Couple Bootstrapped RuffleButts To $5M

RuffleButts is a perfect story on how to bootstrap with a paycheck. Founder CEO Amber Schaub started RuffleButts, a children’s apparel company, in March of 2007, backed by her husband’s full-time job. He later joined in 2010 as the COO, after the company had gained traction. Here is our conversation from 2014.

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Best of Bootstrapping: E-commerce and Investing with Tod Francis, Shasta Ventures

If you have been bootstrapping and think you are ready for investors, you need to learn how investors think. First, please study our free Bootstrapping course and Investor Introductions page. Then start looking for entrepreneur – investor fit. Today I introduce you to Tod Francis.

Tod Francis, Managing Director at Shasta Ventures, starts with a discussion on the history of retail, all the way from shoe stores, to departmental stores, and back to specialty retail. This is followed by a similar overview of the history of e-commerce ranging from Amazon’s strategy to how specialty retail is translating into niche e-commerce, and how Tod is looking at investments in the category. You can listen to the podcast interview here and the entire roundtable program here:

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Best of Bootstrapping: JAM CEO Survives Covid with a Bootstrapped Venture

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

Kristi Herold, CEO of JAM, built a thriving bootstrapped business over twenty years until Covid hit. Read how she is surviving Covid.

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?

Kristi Herold: I grew up in a small city called Sudbury, Ontario. It is about four hours north of Toronto. I have two older brothers and a very supportive mother and father who encouraged us to get involved in sports. They taught us to do what we wanted in our life. My father is an entrepreneur. My grandfather was an entrepreneur as well. I followed the footsteps of both my brothers to be entrepreneurial going through high school and university.

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Surviving Covid with a Bootstrapped Venture: Kristi Herold, CEO of JAM (Part 6)

Sramana Mitra: Has your sports league business come to a complete standstill? 

Kristi Herold: Yes, it’s gone, but it will come back. 

Sramana Mitra: Yes, it will come back, but you will just have to survive this period. 

Surviving Covid with a Bootstrapped Venture: Kristi Herold, CEO of JAM (Part 5)

Sramana Mitra: It also depends on what you are trying to accomplish because cash acquisitions are easy to rationalize on your balance sheet. If it’s an equity acquisition joint venture with another player, then that is not so easy to value. That is why I was probing that issue. Let’s go back to what happened when the pandemic strikes. How did you orchestrate and move forward?

Kristi Herold: As I said, we had two deals that we were doing our due diligence on that would have doubled the size of our organization by May or June of 2020. We had to put a pause on both of those. We were anticipating that we were going to be shut down for a month or two. I wasn’t anticipating that we would be here 13 months later not being to operate our sports league.