It's Never Too Late for Me, BoJack Horseman, or You

In December 2014, I was given a Most Admired CEO Award by the Philadelphia Business Journal in the Entrepreneur category along with four of my peers. I was humbled and honored to receive it. At the awards banquet, other winners and colleagues inquired about my business, Trajectify. I could see the curiosity in their eyes when I told them that I had started the company a year ago and was still the only full-time employee. Yes, I had previously run other companies, some with as many as 500 employees, but on that day I was recognized as being admired as the CEO of one!

After a moment of wondering whether I should feel guilty, I realized how proud I was. I had never been recognized for my leadership in such a way, despite the number of companies that I had started, grown, or led. I never made the 30 under 30 list. I never made the 40 under 40 list. I am pretty sure there isn't a 50 over 50 list. While I felt successful and knew I had the admiration of those who had worked with me, there weren't any awards on my mantle. You were damned right that I was going to accept this award with a big smile and a lot of pride.

I turned 50 a couple of years ago while I was helping build Real Food Works. Later that year, I started Trajectify, and then another tech startup - IntroNet - and if that wasn't enough, created the Philly New Technology Meetup which in only nine months grew to 1,400 members and was selling out 250+ people events. Admirable, right? Award-winning!

BoJack Horseman

About the same time that I was informed about receiving the award, I was watching BoJack Horseman on Netflix. It's an animated series about a horse who was a former star sitcom actor, who subsequently wasted years of his life basking in the money and glory as a C-list celebrity, but now at 50 years old sought more meaning. The writing and acting is really good and, once you get past all the anthropomorphized characters, you start to see the depth and darkness in the comedy. I was surprised that I liked the series, and even more so that I was personally relating to BoJack. The similarity wasn't with BoJack's wealth, debauchery, addictions, or wasted years.

Where I found a bond with BoJack was that each of us was looking to be more and do more despite having turned 50. When BoJack tells his agent, Princess Carolyn, that he wants to play the role of Secretariat in an upcoming movie, she asks, "Aren't you very too old?" He does get that part (though maybe by accident). He also writes his memoir, learning a lot about himself through the relationship with his ghostwriter, Diane Nguyen, who in a moment of mutual introspection says, "I kind of think that all you are is the things that you do." BoJack eventually wins a Golden Globe for his memoir and spends the episode walking around with the award everywhere. Right back at you, BoJack!

Entrepreneurship Favors Youth

Entrepreneurship, like Hollywood, favors youth. There's a lot already written about it, so I won't use this post to go into detail or debate it. (Just look at the average age of the founders that are getting venture funding or accepted into accelerators and tell me otherwise.) It's in part why I started the incubator, Novotorium (Visionaries come in all ages, though I am no longer affiliated with the incubator). At Trajectify, I now coach entrepreneurs of all ages, but I do meet a lot like myself who are 35 and older. In many cases, they appear to be discouraged by the ageism they feel and see. It's part of my coaching to help break such limiting mindsets and not let obstacles - real or perceived - get in the way of achieving goals.

If you're an entrepreneur that's starting later in your career, or beginning to consider it, there are ways it gives you advantage over your more youthful peers. Here are four reasons how your stage of life makes you a different entrepreneur.

1. Financial Means and Needs

Cash flow and cash reserves are both an opportunity and a threat to the older entrepreneur. Typically, there are savings, friends and family with capital, or a working spouse that can help get the business running and give some room to develop traction. The older you get, the more places you may know to find capital. There are also opportunities to leverage existing business relationships and job experiences to keep cash coming in to allow bootstrapping (often in the form of a consulting "gig").

Organic cash flow tends to be important to older entrepreneurs. There might be personal financial obligations that  require consideration - mortgages, tuition, elder care for our parents - along with a realization that retirement is growing closer. Starting a business as a second career more equally balances the decision to build one that is lifestyle-driven (where the entrepreneur holds most equity and aims for profitability) or one that is short-term value-driven (where the entrepreneur leverages their equity in the business to build more quickly with the expectation of selling or exiting).

2. Risk Avoidance and Tolerance

Despite greater experience, older entrepreneurs seem to be less tolerant of risk. The lessons that we've learned - good or hard - cause us to develop life scripts that we can't easily unwind. As employees, parents, or community members, we often hold on too tight to the things we wished we had done differently. We've had more time to look at the world from the inside-out, develop strong opinions and judgments, and shape our world into one which is safe and comfortable.

Breaking out of those comfort zones is ultimately what leads to growth in our performance. For example, I get far more requests from entrepreneurs who build a business later in their career for me to sign their NDA (non-disclosure or confidentiality agreement) - worried that I may be out to steal their new idea. Those who share their idea more freely are far more likely to be included in the ecosystem that better provides for progress and innovation. If I know what you're working on, I am much more likely to help, make introductions or offer resources.

I have seen experience also work in the opposite, and more positive way - to build stamina and resilience. Those who have been defeated before and recovered can be less likely to let such fear deter them in the future. These are the types of life scripts that should be harnessed when building a new business. To be a successful entrepreneur. it is important to take life's lessons and use them to grow, not to enclose or protect.

3. Skills Through Experience

That experience is important may go without saying, but you have to understand and believe it. I have heard investors say that they prefer to fund young entrepreneurs because they're less encumbered by experience - so more likely to think out of the box and take risks. That only works for the spaghetti-on-the-wall investor or accelerator, throwing funds to a dozen entrepreneurs to see which one sticks. The fact is, when you're an entrepreneur, there is only one business that matters - yours! That others may discount the downside of your experience should make no difference. Your experience is what made you able to reach this milestone. It's what differentiates you from your peers.

Your career has allowed you to develop skills. A good set of skills is what makes acquiring knowledge possible. I, for example, learned to program computers in Fortran and Pascal while in college, but what's that worth now? It's the skills that I developed working as a software engineer that allowed me to eventually pick up and use any programming language. Skills are transferable. When I moved from being an engineer to being a engineering manager, I developed leadership skills that became transferable, so I could eventually lead non-technical groups and, ultimately, the whole business. Developing skills takes time. Skills over knowledge comes with age.

Time has also allowed you to see successes and failures, to learn how to cope with challenges and celebrate successes. The power of observation is the best way to have learned - and cannot be done in a classroom. We learn the most through our eyes. In real-life scenarios, you see the effects of culture, develop models, and understand behavior. Over time, you have graduated from imitating to synthesizing. This learning is the deepest kind and one that cannot be done quickly.

4. Professional and Personal Support

In your years of experience, you have not only developed skills and gained knowledge, but also made connections. You have a professional network. There is no way to build a meaningful network without the investment of time. Don't be fooled by LinkedIn connections - an online social network does not have the same capability as your true professional network. The connections that are important to you now are the ones that have developed into relationships. (Check out Judy Robinett's 5+50+100 rule.)

You also have developed a deeper personal network, including family, friends, and colleagues who care about you as a person. There is no way to build a business without a strong professional and personal support system. Entrepreneurs of all ages can become well-connected. It takes more than connections to support you in building a business. You need the advice, time, and caring from others to keep you moving forward - and sane - during what will often be challenging, frustrating, and demoralizing periods of the growth of your business.


It wasn't until recently that I realized it has taken me over 25 years of career and experience to be able to fully appreciate what I am able to do today. Had I won Most Admired CEO 15 years ago when I was running a 500-person organization, it would not have meant as much as it did winning it now at Trajectify.

If you're someone who has had a good career, or perhaps one that was cut short, or choose to make a change later in life and take control, then just do it! It's highly likely that you have everything you need to be successful. If you're an investor in young companies, or a service provider or peer to them, don't discount age, else you might miss some great opportunities. If you're the media, then note that we're likely the ones keeping your advertisers in business, spending the most on products and services.

Finally, watch BoJack Horseman, learn to enjoy and appreciate it the way I did - its depth provides an opportunity to maybe see yourself from the outside-in and get the courage to become a better version of you and do more!