Bobby Brannigan: How I Went From $250k In Debt To $85 Million Exit

Bobby Brannigan escaped hundreds of thousands of dollars in debt and sold his company for tens of millions of dollars. Here's how he did it.

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We did a thing…

I was up all night thinking about how to announce this, but f*ck it. Here I go. I’ve spent the last three years interviewing founders and sharing the stories of Warby Parker, Zillow, Rippling, Uber, etc.

7+ Million views and counting we’ve learned a thing or two about what makes a compelling story.

So, for the readers of this newsletter, I am offering a FREE 30-minute marketing strategy consultation for your business. You can redeem the offer here.

P.S. The link expires in 72 hours, so make sure you grab a time early; there are limited spots remaining.

Thank you for all of your support. I would not have been able to do any of this without you. Now, onto the story of ValoreBooks.

Founder, Bobby Brannigan shares the story:

“It started at the end of my freshman year. I went to the bookstore to sell my books, as most students do, and they wouldn't buy half the books. So I asked the rep, ‘What do you want me to do with these books?’ She's like, ‘You can throw them in that pile over there.’

So I look at the pile, I'm like, ‘Wait a second, can I have the pile?’ She's like, ‘Sure.’ So my friend and I brought them back to my room, and within a week and a half, I sold them for like $5,000 on eBay. That was my ‘Oh sh*t’ moment.

When I came back the next semester, I was like, ‘Okay, game time; I got to get my hands on a lot more books.’

My first thought was, ‘Let me just put up posters around campus, in the dorm rooms, and the dorm bathrooms.’ I told the RAs and all over I would post these posters that I printed in the college library.

It said, ‘If you have books to sell, email me the ISBN numbers, and I'll give you a price. If you like it, I’ll pick them up, and you can give me cash.’

Q: How successful were those posters in bringing in customers?

“Yeah, I think it was somewhere between like $500-800 a week in books I would buy, and I usually like double, triple, and quadruple my money. So, in the beginning, it was obviously pretty good.”

Q: How much did you bootstrap the company with?

“That's a good question.

The amounts fluctuated because what we were doing was flipping textbooks along the way and generating profit. We made $5-7 million in profit to fund the development of the [textbook] marketplace. But we also had to borrow money to do so, and we did so in very unconventional ways. We were able to amass, I think, $250k in credit card debt, and we actually had a person who managed a baseball card binder with all the credit cards in it.

Second, my father let me take out a home equity loan on his house.

[And third], we borrowed money from people, I'll call it, on the streets of Brooklyn, and if I didn't pay the people on the streets, I would have gotten my legs chopped off. So we were pretty extreme. I will say I was a very confident student. I didn't think anything could stop me. So, I took major risks.

[But it was extremely stressful] I remember driving on the highway in Buffalo, on I-90, and I remember blacking out while I was driving. I woke up on the side of the highway and was like, ‘What the hell is this?’ 

So, a few months later, I put my friend Scott in charge of the textbook marketplace while I took a month off.”

Q: How did you go from those few million in sales to that 85 million exit?

“What I ended up doing for the first time ever in the company. It's kind of crazy. I started talking to the customer, and our customer was the merchant. One of the most memorable was a guy named James Barnes who flew out to Little Rock, Arkansas and had a steak dinner with him and his whole team, which was like 10 of them.

I asked them, ‘What can I do to help them grow your business?’ They said, ‘Help us buy more books. We don't care about selling books. We sell with you because you de-risk us from depending on Amazon. We'll buy an unlimited amount.’

I immediately had an idea. I said, ‘Alright, would you want to bid on them? If you could bid on them, would you be okay with getting them in four months? And would you be able to give us a price four months in advance that we could power rentals with?’

That seems good. Let's do it. That was our moment where it's like, Oh my gosh, for seven years, I've been begging people to get in the marketplace. And now they're coming up like texting me, calling me, LinkedIn messaging me, ‘Can I be a part of this bid opportunity?’ So, that's what grew the company. It was purely innovation and asking the customer what they wanted.”

Q: What was the story of when you decided to sell the business? How did that go?

“Well, at that point, I had everything in the company. I wasn’t borrowing money from the scary people in Brooklyn anymore but I still had a home equity line at my parents’s house, and credit card debt, and like all these things. And all of my money was in the company, right? Like everything. So we're like, ‘What do we do?’

So, we started searching. We hired a banker. We talked to a bunch of people, and we found an unconventional opportunity. We ended up finding a company in Boston that was kind of like the kayak for student loans, and the founder of that company had a vision to partner. We ended up getting acquired by them, and they eventually got acquired by LendingTree.

But, it ended up being a great, great partnership because they had been in student loans for a long time, and they had other ways of getting traffic, and they had millions of customers, too.”

Q: How did it feel when you sold for tens of millions of dollars?

“It felt amazing. When that wire hit my account. I remember pumping in my headphones. I'm walking around Boston, blasting It Was All A Dream by Biggie Smalls on my headphones and just walking like I could have been floating.”

For the full story, you can listen to my full interview with Bobby Brannigan on Apple Podcasts, Spotify, or by clicking the image below.

Have a productive week!


Founder of Dealroom Media