Building Entrepreneurs: Interview with Jenn Maher

“Fail fast.” – Jenn Maher

Jenn Maher is the CEO of, the nation’s largest network of incubators that cultivates and empowers startup ecosystems. Jenn started her professional career as an attorney with an AmLaw 100 law firm in Philadelphia. While practicing full-time, she co-founded Benjamin’s Desk in 2011, which later merged with 1776 in 2017. After ten years of private practice, Jenn left the corporate world to jump full-time into the world of being an entrepreneur. In this interview, she discusses her journey in building up 1776, as well as her advice for aspiring entrepreneurs.

Q. Can you tell our readers how you got to where you are today?

“Like a lot of entrepreneurs, it was not a straight line to get to where I am now. I was very young when I decided I wanted to be an attorney. I went to college, graduated in three years, and went straight to law school because I was so excited. I got what I thought was my dream job, which was a litigation associate position at a big law firm.

It took me about six months to realize that I really did not like it. There was a lack of autonomy and flexibility. Law firm life is very hierarchical; there wasn’t a lot of meritocracy built into the system and that rubbed me the wrong way, because I felt like if I was a really good associate, I should be able to become a partner in five years. I am somebody that likes to accelerate timelines to achieve their goals, so I began plotting my exit strategy, involving myself in real estate, and getting my broker’s license. Very similar to most entrepreneurs’ stories, I began doing this work as a side hustle.

This then transformed into what was then called Benjamin’s Desk, which was a 3000-square foot co-working space that we opened. That eventually grew into 1776, an innovation management company where we partner with higher education institutions, corporate partners, executives, city governments, state governments in a lot of areas, to help entrepreneurs and small businesses grow, and connect them with capital customers and talent.”

Q. What made you decide to merge Benjamin’s Desk with 1776?

“Difficulties come from the business side, the legal side, and the cultural side – it inevitably happens when you’re bringing two organizations of people together. But this is where the risk tolerance came in. We were building Benjamin’s Desk at the time, 1776 was building a really nice company in DC, and we knew the founders. We were sharing resources since we were doing very similar things in different markets.

When presented with an opportunity to merge the companies and have our leadership team takeover, I knew that the deal was difficult, but it was a way for me to double our footprint overnight. That is the risk-reward piece. We had perfected what our model was, and we wanted to do more of that work with startups.

But it is a big build up. There is a diligence process where you go through the whole M&A deal. On the other side of that, you are literally merging systems that each company has. Culturally, it was a shift because I had employees in Philadelphia who were working in the headquarters, and then I had headquarter employees in DC who all of a sudden felt like they were in a satellite location. I ended up splitting my time a lot between both cities.

My team members rose to the occasion to say, ‘this is how we can have empathy,’ and ‘this is how we can build culture’ which actually helped me realize that that is a big weakness of mine. I tend to have blinders on when I am trying to get this deal done and forgetting to consider more of the human side of things. This deal ultimately gave an opportunity for other people on my team to put out their voices and for me to look at their strengths, which I think is one of the best things that you can do as a leader – understand where your own gaps are and fill your team around with people that are smarter than you in those areas.”

Q. Any advice for aspiring future entrepreneurs?

“Some of the common traits of successful companies and entrepreneurs are the team dynamics. That goes back to the ‘surround yourself with people that are smarter than you’ in some of those areas. It is really important to make sure that you are filling in the gaps. There is a self-assessment that needs to happen in terms of pulling those people in.

Also, have empathy and care about the culture, rather than just caring about getting the job done. There are different things that can lead to productivity and passion for people that are working as part of your team. Everybody on your team should constantly feel challenged and motivated and if they are not people that want to feel challenged and motivated as an entrepreneur, then they are probably not right for your team. Additionally, I would say there is a healthy (but hard) balance to strike between making fast decisions and taking time to reflect on what the next move is.

The last is advice that I often give to my niece. She is a 16-year-old who is nationally ranked in the 400m hurdles. She has fallen more than once in the hurdle races and what I’ve said to her is, ‘it doesn’t matter if you fall, it only matters if you get back up again.’ You’ll be knocked down as an entrepreneur over and over again. You won’t give 25 pitches and get 25 investments – you’ll give 25 pitches, and you might get zero. You need to surround yourself with people that sometimes are not entrepreneurs so you can have those different dialogues, but you also need to surround yourself with people that are entrepreneurs that get it. That is why I think the community aspect is so important – you are not doing it alone.”

Q. If our viewers could only take away one message from this interview, what would you want that to be?

“Fail fast. You can waste a lot of resources pushing in one direction over and over again. The definition of insanity is doing the same thing over again, but expecting a different result, so if you’re pushing in that direction and it’s not working, shut it down and move on.

Entrepreneurs and small businesses are not filled with resources in terms of money, resources in terms of time, or any of those things. You have to keep the iteration wheel going. Don’t waste your time just trying to run through the same brick wall over and over again.”

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