The Serial Entrepreneur: Inside Troy Daily's home-grown empire
July 2024
Troy Daily doesn’t have a lot of speeds.
The default is fast, but he can shift to “faster” if the situation merits. His mind is always running, his legs are always moving, his phone is always ringing. There just aren’t a lot of other options when you have so many irons in the fire.
Traverse City’s serial entrepreneur is responsible for a long list of businesses and activities over the past decade, mostly in the tourism, recreation and hospitality arenas. He’s lost count of the LLCs he has (it’s over 20) or the initiatives he’s launched by himself or with others, but on the list are longtime brands like Kayak, Bike & Brew, TC Cycle Pub and Brew Bus along with newer entries like the Daily Blend food truck, Seven Hills and Old Mission Distilling.
All of this while working as a licensed Realtor and a licensed builder, running a property management company and raising three young girls.
When asked about all of this – how it’s possible to handle it all without imploding in on himself like some sort of neutron star – Daily repeatedly credits his wife, Whitney, and his 80-some employees spread across his various businesses. Ideas are fun, he says, but it’s the people around him that truly make the magic happen.
“I just have to give kudos to the whole team. It’s all about my people,” Daily said. “I can’t do what I do without my team, and my trust in my people is the biggest reason for success.”
Homegrown hustle
Daily, 38, is a Traverse City native. His parents, Mary and Brian Daily, owned and ran the Kilwins on Front Street for three decades before retiring last year. It was in that shop that the younger Daily’s appreciation for small business (and his entrepreneurial spirit) were kindled.
“I saw all these things they had to do to run a profitable business, accounting and things like that, but you also had to understand the hospitality side of it and wrap all of that into it as well. At Kilwins, we always said we sold enjoyment,” he said. “And work ethic is huge. Being able to see my parents work every day, open to close…was inspiring.”
After graduating from Michigan State University with a degree in hospitality business, Daily moved to Virginia to open up a Kilwins there. He ran it for about three years in the midst of the late 2000s economic downturn before closing it and moving back home.
He came back to Traverse City with an idea after seeing something similar to what became the cycle pub during his time in Virginia. He launched the Traverse City version in 2013, marking the formal beginnings of an empire that keeps growing every year.
A large degree of Daily’s success has been harnessing the zeitgeist of combining hospitality with recreation, a trend that rose in lockstep with the Grand Traverse region’s massive growth in food and drink options over the past decade.
“These experience-based things just really exploded,” Daily said. “And we were seeing the growth of all of the breweries and other businesses. It just kept spurring me on. What else can we do?”
Cheers and challenges
The businesses and brands keep coming in part because Daily has what you might describe as a mild addiction to the thrill of launching a new one. Always wanting more is a “curse and a blessing,” he says, but he wouldn’t have it any other way.
“I have so many businesses because I love creating them. It’s my favorite part, by far. I love the startup, all the excitement and marketing that goes into it,” he said. “When it comes to executing and operating, I’m really not all that good, so I hire good people to take it on. You have to hire good people to make sure the dream can become a reality.”
But he’s also practical. The vast majority of what he starts has staying power, and that's because his operations are usually well-researched and based on something he’s determined to be feasible from a business standpoint.
“I really just look for needs in the market,” he said. “The whole kayak experience, for example, was just doing something unique that people wanted to do while visiting these breweries.”
Troy and Whitney Daily with Summer, Violet and Maya.
While there might not be competition to something as broad-reaching as the Daily empire, there is certainly increasing competition for some of his individual brands, especially as more experienced-based recreation comes online. This drives Daily to innovate, and the need to do so is almost always on his mind.
“We need to up our game, keep the model fresh. A lot of my businesses are nine, 10, 11 years old, and we can’t just keep doing the exact same thing we’ve always been doing. People want something new,” he said. “How do you stand out? How do you make yourself unique?”
He also has a keen eye for growth. Cycle Pub has gone from one bike to four. Brew Bus went from one bus to 16. Suds and Snow started with 600 people and recently had more than 3,500 people. But he insists to himself and to his staff that growth will never mean a reduction in quality, safety or principles.
"I pride myself in being a local," he said. "I live here too, and I always want to have a reputation for doing things the right way."
Many of Daily’s businesses involve alcohol, which is always a sticky wicket when it comes to public perception and municipal approvals. He speaks strongly in defense of his business practices, which he says have a big focus on safety and responsibility.
“Whether you like drinking or not, I’m doing things the right way. We’ve never had an accident. We’ve never had any issues. We’ve never had the cops called on us. And we’ve had hundreds of thousands of people without incident because we’re doing it the right way,” he said.
With many of his brands catering to tourists, Daily is also caught in the crosshairs of intense and increasing ire over tourism’s impact on the city.
“Our city is evolving, and it’s changing constantly. Being able to stay in a positive light in what I’m trying to do to grow sustainable business is very hard. The more we have tourism, the less people want it,” he said. “I don’t have all the answers, but I try to do the best I can (in running my operations).”
Like seemingly everyone else on the local business scene, one of Daily’s biggest issues over the last few years has been hiring. This is especially stressful for a man who relies heavily on good talent to run his operations.
“No one wants to work. That’s the reality of it. And if they do, you have to pay them way more than they’re worth to get what you want out of them, and you might not even get that,” he said. “It’s a huge, huge challenge.”
It’s a busy life, but if you’re counting on Daily slowing down any time soon, don’t hold your breath. The only thing that will cause him to pump the brakes is if his schedule starts to have a negative impact on his wife and kids.
“My wife holds it all together, and it’s not easy, dealing with someone like me who can’t really turn it off,” he said. “But at the end of the day, everything I’m doing I’m doing for my family.”
An incomplete look at some of the business, brands, events or initiatives Daily has launched:
2013 - TC Cycle Pub
2013 - Paddle For Pints
2014 - Kayak, Bike & Brew
2014 - Brew Bus
2014 - Daily Blend
2015 - TC Ale Trail
2015 - Purchased Suds & Snow
2017 - Flapjack & Flannel Festival
2017 - Strongbrew Cold Brew Coffee
2017 - Alley's Market
2019 - Elevated Property Management (now Elevated Homes & Hospitality)
2019 - Old Mission Holdings (construction)
2020 - Jacob's Farm revamp
2021 - Obtained real estate license
2023 - Seven Hills and Old Mission Distilling
2024 - Obtained builder's license
TCBN cover photo by Meg Warzywak-Bowen
