3 Factors to Consider Before Exiting Your Startup

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When I was approached by Microsoft to acquire my company as a young entrepreneur in my 20s, I leaped at the opportunity — well, who wouldn’t?

To give a little background: A college friend and I had become interested in certain facets of cybersecurity and took it upon ourselves to develop anti-spam software, swiftly followed by anti-spyware software. This was before machine-learning technology was around, but big data was already a buzzword. We successfully launched GIANT Software, and our company quickly grew exponentially.

Only a year into releasing our flagship product, Microsoft reached out to us. They loved what our technology offered and within a short time span, GIANT became Microsoft Anti-Spyware, and my co-founder and I were acqui-hired into the company.

A couple of decades on, and having had the time to muse on past choices, there are a few key elements that I would encourage others in a similar position to ponder before they make a decision.

The grass isn’t always greener

Everyone has 20-20 vision in hindsight. Looking back, there’s an argument to be made that I should’ve held out for longer and not sold my business quite so soon — however, not necessarily for the reasons you might think!

The time immediately after the acquisition was exhilarating. We moved to new offices in a new part of the country, hired hundreds of new people for my team and made use of resources that we never had before. It was truly exciting, and I felt like I was still able to tackle big problems head-on.

However, boredom eventually set in. We went from startup mode to corporate mode so quickly. New processes, systems and internal politics that didn’t exist or weren’t relevant before suddenly became a major part of my day.

If you are an entrepreneur, and your company gets acquired, there’s a chance you might become idle. The day-to-day wasn’t as exciting as it had been, and I was missing the creative buzz, the rush, the “reach for the stars” impetus that you have when you are in the build-up stage.

Have a backup plan

That’s why my next piece of advice is: Always have a backup plan for after your exit. Think about where you want to head next, whether within the same field or coming from a different direction completely. It’s always a good plan to have the next few ideas up your sleeve.

For example, following on from my GIANT venture, I chose to dabble in a number of different areas of tech — including ecommerce, graph theory and consulting. Trying your hand at a number of things and learning through practical experience can offer all sorts of inspiration, as well as help you build your network and make connections.

Finding a colleague or partner who is on the same page as you can also make entrepreneurship more worthwhile at the same time. Two heads are better than one, and collaborating on projects will broaden your horizons. And of course, colleagues who wind down at the end of the day in the same way definitely help with the work-life balance elements — a quick game of Call of Duty anyone?

Love what you’re doing

Are you exiting your startup for the right reasons? Are you handing over the reins in order to head in the right direction? Depending on your set-up, you may continue to be involved in the business, or you may be leaving the business in capable hands and finding yourself with a lot of spare time. When you’ve worked hard to build something up over the years, it can feel a little surreal to hand it over, and the thought of doing it all over again can be overwhelming.

Taking something you are passionate about and turning it into what you do for a living is one of my biggest tips for self-fulfillment. In 2016, I founded Reason Labs as I decided to get back to my roots and re-enter the world of cybersecurity. Today, I continue to do what I love most: finding and mitigating cyber threats with my team of RAV researchers.

Fortunately, my interest in cybersecurity also comes during an era whereby large businesses and individuals are all avidly seeking to amp up their cyber protection. It’s a field that currently has a large scope for innovation, and working within a field that I personally find exciting means that work doesn’t ever feel like work.

Of course, this is easier said than done, and learning from past mishaps, decisions and maneuvers are all ingredients that will direct a person in their working life. And as always, taking advice and learning from others who have been in similar situations will aid you in carefully considering all aspects before making a life-changing move and in making decisions that are right for you and your company.