15 Years Later: Lessons Learned In Building an Entrepreneur Ecosystem

Brian Raney

Brian Raney, Co-Founder & CEO of Awesome Inc

April 17, 2024

In 2007, Luke Murray and I walked into President Lee Todd’s office at the University of Kentucky, unsure if we should take the first step in starting our own company. In that one-hour meeting, President Todd inspired and encouraged us to pursue a career in entrepreneurship. He didn’t write us a check to be our first investor. He didn’t help us hire our first employee OR even find our first customer. He simply gave us the confidence and permission to try (and fail) at our passion of being an entrepreneur. A few months later, I started my first software company, APAX Software. Then in 2009, Luke and I decided we wanted to do for others what President Todd did for us. We started Awesome Inc to help build an entrepreneurial community in Kentucky so that others could pursue their definition of awesome.

Over the past 15 years of community building, we’ve learned a few things. This post serves as a summary of some of the top lessons we’ve learned.

Define your values, and let them guide your every move.

We established our core values in the 2nd year of Awesome Inc. That worked out pretty well. It gave us some time to find out what mattered to us, but was early enough that we weren’t too established with any of our programming yet. Our values - 1) Be Good, 2) Be Excellent, 3) Be a Friend, and 4) Be You - guide all of our decision making internally at Awesome Inc and in the way we go about building the community around us. You’ll see them referenced many times in this blog post alone…and if you ever visit Awesome Inc, they're hanging on the wall right by the front door, reminding everyone how it all starts with those four core values.

Don’t recreate what’s already been proven to work.

In 2008, the year before we started Awesome Inc, our founding team took a trip to Boulder, CO to visit Techstars (a trip that was funded with personal money from Vice Mayor Gray at the time). We met with dozens of leaders in the Boulder startup community, including Brad Feld and David Cohen. The transparency and openness that those two shared with us as to what worked in building the Boulder community has been the foundation of a lot of what we’ve built in Lexington. Over the last 15 years, we’ve visited other communities to learn from them. Places like Austin, TX, Nashville, TN, Raleigh-Durham, NC, Providence, RI, Boston, MA, San Francisco, CA, and Columbus, OH all have proven concepts and elements of their communities that we’ve implemented in Lexington. We’ve certainly tweaked parts of these learnings to what works best for our community, but I would estimate that we’ve copied greater than 50% of what we do from other startup communities.

Play the long game.

Part of the reason Brad Feld says that entrepreneurial communities need to be led by entrepreneurs in his book Startup Communities, is that you have to have a long term view on the community. Entrepreneurs are the most likely players in the startup community to be around long term. Many of the other players in the community won't be around long term. Universities function in a one-year time horizon (and they have the summer off). Government functions in two-to-four year rhythms. Universities and governments also have strong hierarchies that want to impose structure. That’s not how entrepreneurship works or how a startup community evolves.

On top of all of that, universities have mis-aligned incentives with their student entrepreneurs. If a student is successful in launching a business, the best thing for that student to do is drop out of school and focus on their business. That’s not what the university wants though.

As an entrepreneur, you have a long term view. In order to be successful, it’s going to take you 10-20 years to create a company (at least for most companies). The startup community needs that kind of long term thinking.
Over the past 15 years we’ve been able to build a pipeline of programming that spans over the lifetime of a startup. In the early stages, we have things like Startup Weekend and 5 Across, which provide entrepreneurs a place to test their ideas and get early feedback from others in the community. Once some traction is developed we encourage startups to apply to our accelerator program, the Awesome Fellowship, where they can gain access to valuable resources such as a mentor network, physical space, and tech resources. As the startup grows even more, we have a venture fund that can provide capital and more experience. And for those that make it to the pinnacle of success, we’ve created the Entrepreneur Hall of Fame to celebrate and raise awareness.

A great example of a local entrepreneur who has worked their way through this pipeline is Sam Razor, from Hippo Manager. Sam pitched at 5 Across in 2013. He joined the Fellowship program in 2015. He was funded by one of our funds later that year. And had an exit in 2021. He was inducted as an emerging entrepreneur into the Hall of Fame and I suspect he will start another company that will be even more successful someday in the future.

This pipeline took a long time to build and it takes hard work to maintain. We’ve had to stay disciplined to a long term view and build the right partnership in order to execute.

Find the right partners.

We’ve had a lot of really great partners. Let me highlight one of them - Kinetic by Windstream. This relationship started from one of the Windstream team members, Tim Williamson, attending 5 Across. He fell in love with the event and became a regular. Then Tim did something that is the number one sign of a great partner - he gave first. He offered to meet with us to discuss what it would look like for Windstream to give Awesome Inc free high speed internet for our co-working space. From there, we established a 5 Across sponsorship package and the relationship has been thriving for years.

The right partners don’t take a lot of sales efforts or convincing. They see the value in the relationship and are willing to give first to demonstrate the sincerity of their commitment. The right partners understand what it means to Be a Friend.

Build for the market you WANT to serve and engage with.

In 2009, my business partners and I scraped more gum off the carpets of Awesome Inc than any 25 year old could have possibly consumed in their lifetime. Every weekend around 2am, the three of us would be sitting on the floor with an ice cube and knife trying to clean up the gum stuck to the carpet from some rap party, sorority social, or Holiday celebration. Mostly because demand was high for a venue like ours in downtown Lexington and we saw it as an opportunity to pay the rent, our entrepreneurial epicenter had turned into a nightclub on the weekends. These events had nothing to do with entrepreneurship and were taking up massive amounts of our time and energy.

I’ve watched so many companies be distracted by trying to create a product that is “something for everyone”. It doesn’t work out and they usually end up being “nothing for everyone”. The same goes for community building. If you try to create a space or program or event or newsletter or podcast that is “for everyone”, you are likely going to end up with something that isn’t valuable for anyone. This doesn’t mean don’t listen to your customers or the market. It does mean that you have to decide what customers you want to serve and how you want to serve them.

For Awesome Inc, we’ve had to learn this the hard way. When we first started we tried to be everything for everyone. Our co-working space was used as an office space during the day, a dance studio on certain nights, an art studio on certain nights, a venue for parties on the weekends…it was not only exhausting, but we weren’t excellent at any of it (CV #2). We didn’t actually want to be doing most of those things. They were just things that people were asking for. After about two years, we really honed in on the market we wanted to serve and started creating programs that targeted those people.

Another part of this is to constantly be engaging new people that fit that profile and try to activate them into the community. The Awesome Fund is a great example of this. About half of the LPs in our fund are first time startup investors. However, 100% of the LPs fit the criteria that we set out to attract from the launch of the fund. They all “get it”, as in they understand our mission and desire to be entrepreneur friendly. They are all in line with our mission and core values. And they are all people that pass the “road trip test”, something that we define as: we would choose to hang out with them on a 4 hour road trip.”
The same goes for the companies that we invest in.

Stick to your values. #GameGame.

Processes can change. Principles don’t.

Every organization is going to be tested from time to time by certain external forces to sway from their core values. Whether it’s money, power, laziness, hard times…these forces will tempt you and cause you to question what compass you should follow. The answer is to always stick to your core values and be confident that game will recognize game (ie. you will attract the type of people that you want to attract). This is an important aspect of core value #4: Be You. When people ask me how do you decide what hill to die on? I point to our core values. Over the last 15 years we’ve adapted and changed a lot in our process and programming at Awesome Inc. However, we’ve not changed our principles or values.

Entrepreneur first.

There are lots of stakeholders in building an entrepreneur community. They all have different priorities and preferences. The entrepreneur’s priorities have to come first.

If your community is going to have any staying power, it better prioritize the people that it’s designed to serve. Our people are the entrepreneurs themselves. We treat them with respect (CV #1: Be Good) and give them our best version everyday (CV #2: Be Excellent).

If you were to design an elementary school, you would have lots of stakeholders. There would be students, parents, teachers, and others. You’d need to decide who you want to focus on serving and prioritize their needs first. Different schools may have different answers. The important part is to have the answer figured out for your school and build around that stakeholder.


We need more local venture capital.

Capital scarcity is a real issue and there is always an imbalance between capital and deals. Venture capital is a service function just like legal and accounting services. It services business, but is not the reason businesses exist in the first place. Also, venture capital doesn’t have to be found in your city. We operate in a very flat environment.

We need a centralized community. Everyone needs to be organized.

The community can definitely benefit with increased organization, but it’s not a necessity, and if the desire for organization trumps action, then the growth of your community will be hindered. We have always erred on the side of action over inaction. We’ve treated the growth of the startup community similar to the ideal growth of a startup itself and followed Lean Startup methodology in our approach. Reference In2Lex and StartupLex and TAB.

**We need a hierarchy. **

According to Brad Feld in his book Startup Communities: second edition (2020), this is not only a misconception, but can be a dangerous approach. Entrepreneurs don’t like gatekeepers. They don’t care about power. They care about impact. Community building should be done as a network of nodes. Some nodes may be much larger than other nodes, but certain nodes need not report to other nodes. This is why universities and governments will struggle to be leaders of an entrepreneurial community. They tend to default to a hierarchical and gatekeeper model.

I should wait until it’s perfect before trying it.

On July 17th, 1955, just hours before Disneyland was about to open their park for the very first time, they had helicopters flying over the park in order to dry the asphalt. That’s how close they were cutting it to actually being ready to open their park. Turns out, they didn’t dry the asphalt all the way, Disneyland opened their park and a women's high-heel shoe got stuck in the wet asphalt of Main Street USA. Let this be a lesson to everyone who is starting anything to launch early, well before you are comfortable that you have everything just right.

Eric Ries talks about it in his book The Lean Startup (2011), you should not wait for your product to be perfect to launch it. In fact, if you aren’t at least a little bit embarrassed by the first version of your product, then you probably waited too long to launch. The same goes for any program, event, or activity in your startup community. Just launch.

We need to be like Silicon Valley.

While it is great to implement ideas from other successful startup communities, you don’t need to be the next Silicon Valley. Countless communities have tried to emulate the Silicon Valley model and failed. It’s easy to see why communities want to be like Silicon Valley. With over a hundred billion dollar “unicorn” startups and exponential growth of startup activity over the past couple decades, there is a lot to envy. However, every region needs to play to its own strengths. Trying to model the exact same characteristics from Silicon Valley in a community like Lexington, KY becomes a major disadvantage. Lexington has so much to offer that the Bay Area doesn’t have - such as a tighter knit community, a lower cost of living (that leads to lower cost of resources), a population with an extremely high work ethic, accessibility to other parts of the country.
We aren’t Silicon Valley. We will never be. And we don’t really want to be either…If we did, then we’d just all move to Silicon Valley.

Looking back at the last 15 years, we’re thankful for that meeting with President Lee Todd, and for the inspiration he provided. We’re grateful for the efforts and the support of so many.

Looking forward, by applying the lessons we’ve learned, the potential for our startup community in Kentucky over the next 15 years is beyond what we can imagine. We can’t wait to help so many more pursue their definition of awesome!