Jenny and Tyler Sherman relied on $5,000 micro-investments from friends to kickstart their small downtown dining empire.

Jenny and Tyler Sherman relied on $5,000 micro-investments from friends to kickstart their small downtown dining empire.

Jenny and Tyler Sherman first met at the Mining Exchange in the 2000s — Tyler was the general manager tasked by owner Perry Sanders with opening the hotel. Jenny was the general manager of the hotel’s restaurant, Springs Orleans.

The couple has since moved on from working for others in the hospitality industry, opening not one, but two restaurants — Odyssey Gastropub and The Bench — in downtown Colorado Springs within a four-year period.

“The whole conversation started with, ‘If someone else can do it, we can do it,’” Tyler said. “We had the experience — we just didn’t have the money.”

‘The Odyssey of sports bars’

The Shermans solved their funding issue through micro-investments from friends.

“At the time it was $5,000 for a share and we were able to get quite a few — I think it was in the low 20s — from a lot of local people,” Tyler said. “We were able to get somebody who, even though they don’t own a large percentage, could talk about the restaurant they are a part of.”

Tyler said “everything was fortuitous” when opening Odyssey in 2014. “We had the idea and were looking for a place. At the time, Tony’s was getting ready to move and go across [Tejon Street]. It was the perfect thing. It was the right size — not too big. You’re not trying to fill a 400-seat restaurant as part of your first venture into the business but it’s also not 20 seats and there’s no way to make any money. And it was an established location right downtown.

“We got in at the right time with the right concept and got our investors and it was really on a shoestring budget. We did the whole renovation ourselves.”

The Shermans have since bought out their investors at Odyssey. And it was during the first couple years operating their first restaurant that they began to see a trend.

“You start to see the people coming in and what they’re coming in for,” Tyler said. “I think, the first year, we won a best spot for a blind date. But we also had people coming in for sporting events. They wanted to come to our place rather than a Buffalo Wild Wings because they wanted better food, they wanted to watch the event but didn’t want to be in a super-bright, super-commercial place. So we thought, ‘What if we could do the Odyssey of sports bars?’”

‘A lot of stuff’

The Bench, the Shermans’ sportier-themed venture, opened at 424 S. Nevada Ave. in April 2018. But leasing a building that had housed restaurants and bars for more than a generation was no easy task.

“There was a lot of stuff. This building had been neglected for decades,” Tyler said.

“It had been Will’s Sports Pub, then became the Brickhouse Bar and Grill. That changed hands and the last person who had it went through [the TV show] ‘Bar Rescue’ and it became Garrison Tavern.

“All [‘Bar Rescue’] did was put Band-Aids on things but never really fixed anything.

“We had to do a lot of that. For instance, the building had termites, which isn’t super common and we had it treated at the beginning of the renovation. … This has also been a restaurant since the ’60s and has never had a grease interceptor. That is an absolutely, iron clad, required-by-law thing you have to have. It cost us about $50,000 and was not budgeted for.”

And even with both operations running smoothly, there continue to be challenges, the Shermans said.

One example is the state’s minimum wage laws. Colorado employees making minimum wage receive $11.10 an hour and that will climb to $12 next year.

“It affects everybody,” Tyler said. “There’s no way for it not to. I won’t identify that as a reason — we won’t go out of business because of the minimum wage hike, but it makes things tighter. So we have to raise our prices when we do a menu change. Not dramatically — we don’t have to raise something $3 or $4 — but you’ll see a small increase.

“The thing about the minimum wage that’s disappointing to us is it limits our ability to give people merit raises. At Odyssey, we’ve had guys in the kitchen who have been working for us for four years. Even though we’ve given them raises that are ahead of minimum wage, come Jan. 1 they’re making 50 cents more than minimum wage because it goes up every year.”

As for a third concept: Don’t expect to see anything else from the Shermans any time soon.

“It’s like having children. You need a few years to forget. Right now, I’m a firm no,” Jenny said of opening another restaurant.

“We have several other concepts we’d love to do, but things have to be right to approach that,” Tyler said. “We have to find our groove here and get to a comfortable spot. We’d need the right concept in the right location, but we’re not going to push anything.”

Odyssey Gastropub and The Bench

Established: 2014 (Odyssey Gastropub); 2018 (The Bench)

Employees: 48

Location: 311 N. Tejon St. (Odyssey Gastropub); 424 S. Nevada Ave. (The Bench)

Contact:; 719-999-5127;; 719-375-0930