Building a Portfolio of Bootstrapped Businesses: Ryan Millman, CEO of Undigital (Part 3)

Sramana Mitra: How did you build that relationship? That is a journey story that would be interesting.

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Building a Portfolio of Bootstrapped Businesses: Ryan Millman, CEO of Undigital (Part 2)

Sramana Mitra: Was there a business model? Were you monetizing?

Ryan Millman: Yes. Initially, the business model was based on ad revenue – everything in 1999 was ad revenue-based. I figured out how to tie in with some APIs to one of the first digital photograph manufacturers. People could then order the photographs they were seeing. If there was an event, we’d create the digital files and caption it. When you order photographs, we’d send those out digitally to get manufactured and shipped to your house.

So we had both product sales. We had ad revenue and were charging to have photographers on-site at events at these various colleges. So on a weekend, we’d have fifty events. The library of the college was the only place that had free internet at the time, so I’d go there to upload and transfer the files.

It was very busy and exciting. I learned a lot. It wasn’t all that profitable. It wasn’t cashflow negative, but it wasn’t really setting the world on fire. I did that for several years until I pivoted that business to something that became much more profitable, which was taking those annual fraternity and sorority portraits that the first company that wouldn’t partner with me was doing and actually became the market leader in that space at 600 colleges across the country.

Sramana Mitra: I see. So you started direct relationships with these sororities and fraternities and started taking photos for them. And that was paid.

Ryan Millman: Yes, we’d take the pictures annually for every fraternity and sorority member. We’d create what’s called a composite, which is a collection of all those portraits on one big printed sheet. It gets framed and hung on the fraternity or sorority house wall. The parents then order copies of the portraits of their son or daughter.

When we did the first shoot, it was profitable right away. Over the years, we’ve scaled to every college in the country. It’s been a great company. Very early on, I had an early employee who was fantastic. Once we got that business working, I plugged him in to run that business so I could go on and start the next business.

Sramana Mitra: Does that company still go on? Or did you exit?

Ryan Millman: It still goes on today. It’s been a very successful business for us. I personally haven’t been involved with it for over 15 years. We’re still at every college doing annual fraternity and sorority pictures for each organization.

Sramana Mitra: And you still own that company?

Ryan Millman: Correct.

Sramana Mitra: What year did you leave that company’s day-to-day operations?

Ryan Millman: In 2004, as soon as the company was doing well, we had pivoted. We had been producing a lot of photographs and outsourcing it to other partners to manufacture all the different products. It made sense for us to start to insource. So, we bought a very expensive photo printer to bring it in house. We could now start our own business of manufacturing for other photographers across the country.

I started a company in 2004 called Nations Photo Lab. We were one of the fastest growing manufacturers of photo prints and products in the country. That business still exists today. We have hundreds of thousands of customers now, and that’s grown from a single printer to well over 100K square feet of manufacturing space in Maryland and Pennsylvania. We produce every type of photographic product from wedding albums to wall decor, holiday cards, and frame photo prints. We produce anything with a photograph on it for both consumers and high-end photographers, and we private label for a lot of major retailers as well.

Sramana Mitra: So the go-to-market strategies of these two businesses are very different, correct? What go-to-market strategy did you use for the first business? What is the go-to-market strategy for the second business?

Ryan Millman: For Greek Yearbook, as we had been known in the party picture space, we were the cool, hip company that came in. We had already cultivated the relationship specifically with fraternities and sororities all around the country. We had a lot of brand recognition.

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Best of Bootstrapping: Bootstrapped a Generative AI Startup First

Gridspace Co-Founder Anthony Scodary bootstrapped first, then raised money later to build a $10M+ Generative AI Startup. Gridspace is a wonderful case study of a speech technology company on the bleeding edge of Machine Learning and Generative AI. You will learn how the founders managed to bootstrap to large paying customers and then raise strategic funding. You will also learn the nuances of how they used various Open Source components and existing ML models to get to a point where they can afford to develop more original technology. You will also learn the importance of solutions versus technology platforms.

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

Anthony Scodary: I was born in Ohio in Cincinnati, although I grew up in St. Louis, Missouri. I went to Stanford for school. My undergrad was in Physics and grad school was in Aerospace Engineering.

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Building a Portfolio of Bootstrapped Businesses: Ryan Millman, CEO of Undigital (Part 1)

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.

1Mby1M Virtual Accelerator AI Investor Forum: With Sailesh Ramakrishnan, Managing Partner at Rocketship.vc (Part 6)

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.

1Mby1M Virtual Accelerator AI Investor Forum: With Sailesh Ramakrishnan, Managing Partner at Rocketship.vc (Part 5)

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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