Roundtable Recap: September 5 – AI Investment Thesis with Ashish Gupta, Clearvision Ventures

During this week’s roundtable, we had as our guest Ashish Gupta, Partner at Clearvision Ventures. Ashish has been in the industry for a long time and has an interesting perspective on AI investing.

HabitHalo

For our entrepreneur pitch, we had Phil Tran from Indianapolis, Indiana, pitch HabitHalo. We discussed his pre-seed fundraising strategy.

You can listen to the recording of this roundtable here:

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Featured Videos

Cloud Stocks: Analysis of Salesforce’s Tenyx Acquisition

Recently, Salesforce (NYSE: CRM) announced its second quarter results that beat the market expectations and helped the stock climb 4% in the after-hours trading session. The company remains focused on AI, and recently announced the acquisition of Tenyx to continue to add to its AI portfolio.

Bootstrapping to Exit and Bootstrapping Again (and Again): Adam Robinson, CEO of Retention.com and RB2B (Part 3)

Sramana Mitra: Well, I think what you’re pointing out is that if your ad can rattle people enough to get them to comment, it’s with comments and discussions in social media posts that you get distribution. That’s what snowballed the algorithm distribution. So by rattling these people, you were getting that distribution. So whether people liked it, resonated with it or not, you were getting distribution, you were getting your ad in front of enough people who actually were interested in buying.

Adam Robinson: I think a mistake that people can make is that it’s not good for your brand. But when you’re starting a startup, you don’t have a brand. I don’t think you have a brand to ruin until you’re like well past $10 million ARR.

Video FAQs

Best of Bootstrapping: Bootstrapped an IoT Company from NC

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

North Carolina, at one point, had a large concentration of cellular technology companies. Some of that talent then came together around IoT, including Bob Witter, CEO of Device Solutions. He shared his journey with me 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 circumstances?

Bob Witter: I was born in Springville, New York. It’s in the western part of New York. I grew up in central New York. I went to school at State University of New York and graduated in 1981 with degrees in Computer Science and Mathematics. I started my career in Rochester with Eastman Kodak company in the medical products division that was brand new at that time. I learned a great deal about how to do medical products that has certainly served me well even today at Device Solutions.

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Bootstrapping to Exit and Bootstrapping Again (and Again): Adam Robinson, CEO of Retention.com and RB2B (Part 2)

Sramana Mitra: Could you double click down and explain with a bit more color and depth exactly what it was that you were doing at Retention.com, which had a different name at that time. Explain the workflow, the value proposition, and the complexity of it.

Adam Robinson: The value proposition was that we can identify 35% of your web traffic and give you email addresses of people that don’t fill out forms.

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Fred Luddy started ServiceNow, a Multi-Billion Dollar Unicorn, as a solo entrepreneur bootstrapping with a paycheck. Fred shares his early entrepreneurial journey in great depth here.

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Cloud Stocks: NVIDIA Still On a Roll Amid Rising Competition

NVIDIA (NASDAQ: NVDA) last week reported its second quarter results which beat all estimates. However, after three straight quarters of revenue growth above 200%, its growth of 122% seems a tad disappointing and its shares fell 8% in extended trading. This is a slight pullback after an astronomical rally following the AI boom. Its stock has zoomed over 750% since 2023 and 150% this year.

Bootstrapping to Exit and Bootstrapping Again (and Again): Adam Robinson, CEO of Retention.com and RB2B (Part 1)

Adam has bootstrapped his first company to exit, and before the acquisition, incubated his second one within it. He’s repeating the same incubation model by incubating a third company within his second one. Really cool strategy and a great interview.