Are entrepreneurial employees a flight risk?

I recently passed the eight-year mark of running a business and even this many years in, we’re still figuring out who we are as a company.

The last 18 months in Covidland taught me many lessons. Most the hard way.

A big one: clarity on who we should hire and how to manage a team full of high-achievers.

It takes a certain level of risk acceptance to work at a startup. One of my early hires rejected my offer because she was nervous about the size of the company (3 people at the time). Luckily, I was able to talk her into taking the job, and she is now my head of operations.

While many have thrived in our startup environment, some have left for the stability of corporate culture, and several of my former team members now own their own companies. 

Working at a startup requires a very specific set of characteristics:

You must be accepting of risk, hard-working, and willing to perform and adapt in an environment that is constantly changing.

That’s probably why our best-fit team members also happen to be entrepreneurial in one way or another.

At my company, Accelity, we have 17 full-time employees, four of whom are former entrepreneurs, and four others that have side hustles. That means at least 47% of my team is entrepreneurial in some way, shape or form.

To some, that looks like at least 47% of the team is a constant flight risk, but I don’t see it that way.

I think it’s possible to satisfy and retain entrepreneurial people. Heck, my ENTIRE leadership team has run or is running a side hustle. They also have tenures with me of: 12 years (past & current jobs), 6 years, 6 years, 2 years. In the great resignation, I am pretty dang proud of that.

Listen, there is no secret sauce that keeps high-potential employees happy, and some will inevitably move on. But here’s what I’ve found:

  1. You MUST ask your team to step out of their comfort zones to grow from within the company.

    Develop your team constantly. You must challenge the whole person—not just their skills at work.

    Working with my team as a “whole person” instead of a “work person” has allowed me to build a leadership team completely from within.

    When you show your team that you’re here to help them for the long haul, it pays dividends to your business as well.

  2. Encourage employees to have a personal brand.

    A personal brand on company time? Most companies say absolutely not.

    Alternatively, we run contests within Accelity that allow team members to work on their LinkedIn “brand” during Accelity-paid hours.

    We’ve found that when employees have personal brands, it increases prospect and client confidence in their skills while growing website traffic and speeding up the sales process.

    Those are big wins for my company, and my team is having fun, too.

  3. Support team members’ side hustles.

    I always thought that my company was pretty supportive of side hustles, but last year a situation made me realize that we still had a ways to go. We’ve now updated our policies to make them crystal clear and had real, human-to-human (not company-to-employee) conversations with our team about their side hustles and how we can support them.

    If you have creatives on your team, they will have side hustles. Period.

    I want my team to feel safe telling me that they have aspirations outside of my company, because, let’s face it: they do.

    You might as well help them get to their next step, whether it’s in your company or not.


So, is it possible to keep past, current and budding entrepreneurs happy in your startup?

I believe so.

If you want to hire entrepreneurs, intrapreneurs, or high-potential employees (most startups do), you have to take special care of them.

It’s time to break the old corporate rules that say side hustles and personal brands are no-no’s. 

🔥