1Mby1M Virtual Accelerator AI Investor Forum: Lisa Chai, General Partner at Interwoven Ventures (Part 3)

Sramana Mitra: From what I gathered, you are focusing on Vertical AI? Is that a correct observation?

Lisa Chai: We lean heavier towards Vertical AI, but it’s not a mandate.

Sramana Mitra: Okay. Let’s double click down on Vertical AI. We’ll come back to what else you’re doing besides Vertical AI.

Featured Videos

Bootstrapping in the Age of AI

The Age of AI is also the golden age of Bootstrapping. And it is the golden age of Solo Entrepreneurs. With AI, you can build a lot in an ultralight mode and get VCs salivating. The key is Positioning. Let’s discuss the nuances.

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1Mby1M Virtual Accelerator AI Investor Forum: Lisa Chai, General Partner at Interwoven Ventures (Part 2)

Sramana Mitra: What do you want to see in a company? What is the stage of development of the company that you want to see before you’re willing to write a check?

Lisa Chai: We want to see some type of product that you’ve already developed like a demo. If you have a couple of pilot customers, that’s wonderful.

Video FAQs

We Like Bootstrapping to Exit

This week, we’re discussing how the Age of AI is also the golden age of Bootstrapping, and also of Solo Entrepreneurship. Yes, you CAN and SHOULD bootstrap with a Paycheck. Yes, you CAN and SHOULD bootstrap to an Exit.

Are you trying to do a startup as a SOLO entrepreneur? Your time has come.

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Can You Be an Entrepreneur Alone?

Are you trying to do a startup as a SOLO entrepreneur? And are people telling you that you can’t? They’re wrong. You CAN. But there are complexities you need to understand. Let’s discuss the nuances.

Fred Luddy bootstrapped ServiceNow as a Solo entrepreneur bootstrapping with a paycheck. He went on to raise a lot of VC funding. And, he went on to build a Unicorn.

If you are a solo entrepreneur doing a startup for the first time, assume you have to bootstrap.

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1Mby1M Virtual Accelerator AI Investor Forum: Lisa Chai, General Partner at Interwoven Ventures (Part 1)

Lisa Chai, Co-founder and General Partner at Interwoven Ventures, discusses her firm’s investment thesis.

Positioning is Key for Product-Market Fit and Funding

Are you struggling with attracting customers? There’s a very good chance that your Positioning is off. Positioning drives Product Market Fit (PMF). You HAVE to get it right. Let’s discuss how.

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June 19 – 690th 1Mby1M Mentoring Roundtable for Entrepreneurs

Entrepreneurs are invited to the 690th FREE online 1Mby1M Mentoring Roundtable on Thursday, June 19, 2025, 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.

You can learn more here and REGISTER TO PITCH OR ATTEND HERE. Register and you will receive the recording by email, even if you are unable to attend. Please share with any entrepreneurs in your circle who may be Interested.