“I even missed payroll a couple of times”, says entrepreneur Jeremy Greven.
“They say it’s lonely at the top, but, I can tell you, it’s even lonelier when you realize that you can’t pay the people who are working their tails off to keep your business solvent.”
Fast forward a few years, and here’s what Jeremy had to say: “I’m finally enjoying the freedom of my time, listening to the birds, and reinvesting in my family for all of those missed dinners along the way.”
Jeremy went from missing payroll for his 85-employee business to a very successful exit and now a 17-time angel investor inside of 10-years. How did he do that?
Jeremy’s story is truly inspiring, and that’s why we’ve started this new entrepreneurial journey interview series. The plan is to interview entrepreneurs at all stages of their business.
As entrepreneurs, we all have something to learn from one another, and that’s the point. To share stories to inspire you, and to let you know that you’re not alone on this challenging journey. And by the way, if you would like to share your entrepreneurial journey with other fellow entrepreneurs, then please contact me.
Let’s continue with Jeremy’s interview:
What’s your story? Tell us about yourself.
My name is Jeremy Greven, and I am a scale-up advisor for high growth technology companies. I mentor and invest in SaaS-based technology startups through my firm at Six Squared Capital. To date, I have invested in 17 private companies, most of which have gone on to successfully raise Series A & B rounds or to complete a successful exit. I was previously Founder and CEO of Prompt Alert Inc., ranked in Profit Magazine’s Top 500 Fastest Growing Companies and Profit HOT 50 Technology Startups.
Regarding one of your business ventures, either current or past:
What is (was) that business, and what does that business do?
Prompt Alert provides automated communication services. Prompt Alert’s main product, Patient Prompt, provides automated engagement tools to healthcare organizations throughout North America. If you’ve ever received an automated reminder call before your medical appointment, odds are good that it came from Patient Prompt. The system has sent out over 800mm notifications since 2005.
How many years have you run (or did you run) the business, and when did you feel comfortable in the role?
I founded Prompt Alert in 2004. I worked on the business part-time evenings and weekends until 2007 when I left my full-time job to run it. The decision to quit my full-time job came after raising a $250k friends and family round of financing. At the time, I thought this was more money than we could ever spend. I couldn’t have been more wrong. If I was doing it again, I would have halved my sales estimates and doubled my expenses. I personally made less in the next 3 years combined than I did in the year before leaving. Those next three years were exceptionally difficult mentally, financially and emotionally. While struggling to grow the business I also balanced my wedding and the birth of two of my three children. There was a lot going on.
How many employees did the business grow to, or if you’re still running the business, how many employees does the business have now, and at what point(s) did you decide to grow this number?
When I sold the business in June 2014, we had 85 employees spread across North America. Since we were growing a SaaS business organically, we never really had the money to invest ahead of success. This meant that we had to run more or less break even from day one. After we signed a big deal I would think “uh-oh… how are we going to implement this?” There were a lot of long days and more than a few missed family gatherings as the American holidays rarely aligned with those in Canada.
Business Challenge and Success:
Describe the biggest challenge you’ve had to overcome, how it impacted your business, and how it impacted you personally.
I think just about every day was a challenge while growing the business. Nothing came easily and we did not have a big nest egg of capital to draw back on – I even missed payroll a couple of times in the early days because a customer was late paying their invoice. They say it’s lonely at the top, but I can tell you it’s even lonelier when you realize you can’t pay the people who are working their tails off to keep your business solvent.
Describe your biggest success and how it impacted you and your business.
The largest Electronic Medical Records program in the market is called Epic. It is used extensively throughout all major healthcare systems in North America. I believed our technology could work with Epic, but we had never done it before.
Interoperability has come a long way in Healthcare, but 5 or 6 years ago, Epic wouldn’t even talk to you as a vendor until you had one of their clients signed. I eventually decided enough was enough and put a cash bounty on closing our first Epic deal. I personally sat on all tech calls trying to convey confidence over experience to break through the log jam. We put their logo on all of our marketing material and presentations, hoping nobody would call us on who exactly we were working with.
Prospective clients were constantly asking our sales team for Epic references, but we didn’t have any to give! It was a classic chicken and egg scenario. Eventually, we found a client who cared more about our results than our references and they became our first install. From that point forward the dominos all fell into place and Epic soon represented 4 of our 5 biggest clients.
Sometimes you have to fake it until you make it.
Describe a period that really tested your ability as a leader and how you overcame that challenge.
My most challenging period as a leader surrounded the sale of the business. When I announced to the team that we had been acquired, there were literally gasps of disbelief – “How could you sell your baby!?” I remember arguing with the HR people about our ‘Foster Friday’ tradition of a cold beer at our desk late in the week. I was constantly fighting with the leadership of the parent company to defend the culture of the company I had built. I dramatically underestimated the emotional toll selling something I worked so hard to create would be.
Being an entrepreneur and building a business is hard, challenging, and sometimes stressful. As a fellow entrepreneur, it’s helpful to know that you’re not alone in personal challenges.
How did you manage the work/life balance?
In the early years, the balance is 99% work and 1% personal. It took years for the truth to come out from my family about how difficult it was on them. I didn’t recognize this until I sold and flipped the balance in the opposite direction.
How did you manage the work stress?
I wasn’t really aware of the stress until I got out of the business. Now that it’s gone, I’ve started to notice other things in my environment that were gone for a decade or more – In the last few months, I have begun to notice the sound of the birds, the sound of the wind in the trees and even the hum of the refrigerator. I know they were there all those years, but I was too dialed in grinding to even have the capacity to be aware of them. As an entrepreneur, I experienced utopic highs and seemingly bottomless sorrow, occasionally on the same day!
Do you have an exit strategy for your business? If so, what is it? Or if you’ve already exited, what did your exit strategy look like?
One of my best friends and former CFO once told me, “Build a successful business and the exit will take care of itself”. He’s right.
Often, we focus too much on getting to the next phase, trying to plan things too perfectly. I think that’s a fool’s errand. Just be your best, build a company you are proud of with people you love to spend time with. Yes, I sold the company, but I’m far prouder of the people I met along the way.
In a small way, I’m proudest of the fact that I was there to see them meet their partner, get married, buy a house and have kids. The other day I ran into an early employee in the mall. When he saw me, he rushed over, gave me a huge hug an introduced me to his baby daughter. That’s magic.
Money can sometimes be a delicate topic, but many entrepreneurs get into business hoping to hit the financial jackpot. It’s helpful to understand how other successful entrepreneurs deal with money.
Describe your relationship with money, Are you a spender or a saver, and what are your retirement goals (if any)?
Wealth is a by-product of success. I didn’t start out to get rich, I started out to have freedom of my time. I didn’t like having a boss and thought working for yourself meant you could choose how you spent your time. WRONG… Rather than one boss and an annual performance report, you’re now working for EVERYONE with hourly performance reviews. There’s the bank, shareholders, customers, your spouse, employees, etc, etc.. It can be overwhelming. Sleep does not come easily when everyone is counting on you. If you start a company with the sole goal of getting rich, you’re doomed. While there will be thousands of positive experiences along the journey, few (if any) will be financial. In fact, odds are good you will end up poorer than you could ever imagine.
I was fortunate enough to do very well when we sold the business. I have set up my family for generations. Despite the financial freedom, deep down, I miss it… I miss the team, the grind and, oddly, the stress. I’ve walked through a minefield and somehow managed to emerge unscathed. I have not figured out all the answers nor do I know if I have the will to do it again. What I do know is that I learned more about myself than I ever could have imagined.
I’m 41 years old and I need something to do for the next decade. I don’t know if I’ll do it again. I don’t know if I COULD do it again.
For now, I’m finally enjoying the freedom of my time, listening to the birds and reinvesting in my family for all those missed dinners along the way.
I’m looking to chronicle the lives of entrepreneurs who are at any stage in their entrepreneurial journey, whether you’ve just started, or, have had multiple exits. If you would like to be considered for an interview, please contact me.
You can find all of the entrepreneur interviews here.
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Also, I published a book during the summer of 2018, “The Kickass Entrepreneur’s Guide to Investing, Three Simple Steps to Create Massive Wealth with Your Business’s Profits.” It was number 1 on Amazon in both the business and non-fiction sections. You can get a free copy here.