Best of Bootstrapping: Building a Portfolio of Bootstrapped Businesses

Ryan Millman, CEO of Undigital, 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: All right, Ryan. Let’s start at the very beginning of your story. Where are you from? Where were you born, raised? What kind of background?

Ryan Millman: I was born and raised in Baltimore, Maryland. I was raised by two loving parents and grew up with a sister. I had a little bit of a lineage in entrepreneurship. My dad had a small business. My grandfather had a small business. I’d always hear about entrepreneurship from them. Throughout my schooling, I was considered a very poor student. I was very uninterested in my curriculum. My parents were quite concerned about me. I was, however, very much into athletics and pretty much excelled in a lot of the sports that I played.

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Building a Portfolio of Bootstrapped Businesses: Ryan Millman, CEO of Undigital (Part 7)

Sramana Mitra: Category creation is interesting. Let’s talk about category creation.

Ryan Millman: Undigital is a category creator. We’ve invented what we call in-package personalization. Category creation is extremely different. When you go out to a company as a category creator, nobody has you in the budget, right?

Video FAQs

Building a Portfolio of Bootstrapped Businesses: Ryan Millman, CEO of Undigital (Part 6)

Sramana Mitra: Okay. All right. So I understand your business. Where do you go from here?

Ryan Millman: I spend all my time focusing on Undigital, my newest endeavor. It is a little bit related, but it is more of a pure technology company. From a personal perspective, when the companies get big and mature, a lot of your work and effort is focused on HR and admin. I like to be on a small team solving a puzzle that hasn’t yet been solved.

September 26 – 656th 1Mby1M Mentoring Roundtable for Entrepreneurs

Entrepreneurs are invited to the 656th FREE online 1Mby1M Mentoring Roundtable on Thursday, September 26, 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.

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. All are welcome!

655th 1Mby1M Entrepreneurship Podcast with Gaurav Chaturvedi, Kae Capital

Gaurav Chaturvedi, Partner at Kae Capital, discusses the trends he is seeing in the Indian startup ecosystem.

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655th 1Mby1M Roundtable Recording

In case you missed it, you can listen to the recording of this roundtable here:

Roundtable Recap: September 19 – AI Investment Thesis with Gaurav Chaturvedi, Kae Capital

During this week’s roundtable, we had Gaurav Chaturvedi, Partner at Kae Capital, discuss the trends he is seeing in the Indian startup ecosystem.

ManTech Studio

As for pitches, first, we had Prateek Sharma from New Delhi, India, pitch ManTech Studio, a banking software already in revenue.

Endorse.live

Next Milita Datta from Mumbai, India, pitched Endorse.live, a video testimonial collection service.

Both companies are in revenue.

You can listen to the recording of this roundtable here:

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