Best of Bootstrapping: Bootstrapped to Exit from Oklahoma

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

How often do you hear of a successful entrepreneurship story out of Oklahoma? Well, meet Robin Roberson, Co-founder of WeGoLook. This is our conversation from 2015. WeGoLook was acquired by Crawford & Company in 2017.

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 circumstances?

Robin Roberson: I was born in Oklahoma. I was raised, primarily, on a farm. There were about 12 kids in my class. I didn’t know much about the outside world other than what was there in town. I started my entrepreneurial journey in the second grade making yarn belts on the playground. I was able to talk a few of my friends into making them with me. We had quite the distributorship going with yarn belts until the Principal shut us down. When he asked us to stop making yarn belts, I started making Christmas tree ornaments to sell. He shut that down too.

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Featured Videos

1Mby1M Virtual Accelerator AI Investor Forum: With Ashish Gupta, Partner at Clearvision Ventures (Part 3)

Sramana Mitra: So Ashish, I’m gonna switch gears a little bit and ask you about hallucination. Now, here’s an amusing anecdote. A friend of mine sent me a screenshot. He tested what Meta has to say about Sramana Mitra.

Best of Bootstrapping: Bootstrapped a Freemium Business Using a Paycheck

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

Aytekin Tank, Founder and CEO of JotForm, is a Turkish entrepreneur who bootstrapped his company with a paycheck. When we spoke in 2015, he was using a freemium business model, and a virtual team strategy to scale.

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

Aytekin Tank: I was born in Istanbul. I spent my childhood moving from city to city since my family worked for the government. Constantly having to adapt and make friends instilled in me an appreciation for different cultures and meeting new people. We have offices in San Francisco and in Turkey. We have remote workers in 20 countries.

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Video FAQs

1Mby1M Virtual Accelerator AI Investor Forum: With Ashish Gupta, Partner at Clearvision Ventures (Part 2)

Sramana Mitra: I’ve recently talked to a number of people who are looking at the services aspect and the human-in-the-loop aspect. Have you invested in companies with human-in-the-loop?

1Mby1M Virtual Accelerator AI Investor Forum: With Ashish Gupta, Partner at Clearvision Ventures (Part 1)

Ashish Gupta, Partner at Clearvision Ventures, has been in the industry for a long time and has an interesting perspective on AI investing.

Best of Bootstrapping: Peruvian Entrepreneur Bootstrapped to $200 Million

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

We hear a lot from Indian and Chinese entrepreneurs. We hear some from Europeans. But thus far, not as much from Latin American entrepreneurs. WEI President Belisario Rosas is Peruvian, and is also interested in fostering further entrepreneurship in Latin America. This is our conversation from 2015.

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

Belisario Rosas: I was born in Lima, Peru.

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1Mby1M Virtual Accelerator AI Investor Forum: With Yash Hemaraj, General Partner at BGV (Part 6)

Sramana Mitra: I have one last question, Yash, before we adjourn. The SaaS industry has been around for 15-20 years. Around 2008 is when it started really hitting its stride. It’s 2024, so it’s been a while. Then AI came in around 2015-16. Generative AI came in last year. There are cloud companies, SaaS companies, and vertical SaaS companies that are much further along, that have some heft. But now there are AI companies coming into the same markets with AI-enabled solutions, competing with those somewhat hefty vertical SaaS companies. And the answer from the incumbents is, we do co-pilots to introduce AI into the process.

What are you seeing in the market? It’s not a sufficient solution to produce an AI-enabled SaaS application. What is your perspective? What are you seeing in your portfolio?

1Mby1M Virtual Accelerator AI Investor Forum: With Yash Hemaraj, General Partner at BGV (Part 5)

Sramana Mitra: So I think the subtlety here is that if the decision makers are not adjacent decision makers, then the whole sales cycle has to be repeated. You may get a referral that, “Oh, we’re using this product and this product is doing well for us.” Right now, from a technology point of view, the same technology can be applied to a lot of different things. Your agent technology, for instance, can be applied to various use cases—like marketing, human resources, or engineering—but these aren’t adjacent use cases. They’re far apart within an organization, and in a larger enterprise, that adds complexity.