
Ryan has built a portfolio of bootstrapped businesses over the last 25 years that adds up to over $50M in revenue. He discusses the strategies and nuances, pivots and positioning, and more.
>>>Sramana Mitra: I’ve been talking to various people about their various experiments and experiences selling enterprise AI software in vertical AI, and I think this issue is coming up. To train an AI model, you need people who really have deep domain knowledge in that workflow, in the kind of data and the kind of heuristics that they’re applying as human beings to do whatever it is they’re doing. When you’re really trying to automate a lot of stuff that people are doing manually, I think it’s a very delicate balance to get those people to impart that knowledge into training that AI to automate their functions. It’s not been an easy journey for the product people to design, enhance, and get these products to be more effective because of that tension.
>>>Sramana Mitra: Interesting. Let’s just follow through on the same case study of Dili. What is the adoption and what is the experience of the company in gaining adoption around this particular use case?
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Entrepreneurs are invited to the 655th FREE online 1Mby1M Mentoring Roundtable on Thursday, September 19, 2024, 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.
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In case you missed it, you can listen to the recording of this roundtable here:

During this week’s roundtable, we had a full roster of interesting pitches.
Cheenta Academy and Panini8
First, we had Ashani Dasgupta from Kolkata, India, pitch Cheenta Academy. The company has $300k in revenue and needs to figure out a Positioning. Accordingly, a GTM can be derived.
Bharat Finserv
Next Bishnu Mohanty from Mumbai, India, pitched Bharat Finserv. We worked on a crisp elevator pitch.
Proact AI
Then Adarsh Jain from Noida, India, pitched Proact AI, a concept-stage venture focused on addressing retail theft.
College X Connect
Shivanshu Shukla from New Delhi, India, then pitched College X Connect, a proposed platform for exchanging course notes, professional networking, and freelancing.
Gunsens
Next we had Michael Lyon from Fort Myers, Florida, pitch Gunsens, a monitoring and alert system to prevent gun violence.
You can listen to the recording of this roundtable here:
Sramana Mitra: Can we talk about a few use cases of the kinds of companies you’ve invested in with that thesis?
Sailesh Ramakrishnan: Absolutely. I can point to one of each. In the tooling area, we are investors in a company called TALC. TALC tries to solve the problem of how you assess the quality of output coming from an AI system.
>>>Today’s 654th FREE online 1Mby1M Roundtable for Entrepreneurs is starting NOW, on Thursday, September 12, at 8 a.m. PDT / 11 a.m. EDT / 5 p.m. CEST / 8:30 p.m. India IST. CLICK HERE to join. PASSWORD: startup All are welcome!