Maybe I’ve Finally Left Behind the Chaos of Being a Startup

Part of me feels guilty about my new freedom. I catch myself wondering whether I’m doing something wrong. Should I be working harder?

By Ami Kassar

It can be non-stop chaos during the first several years of building a business. There’s no work-life balance. There are no vacations. Weeks and weekends blur together. It can be hard to keep both your business and yourself healthy. Every day, you are fighting to survive until tomorrow, and it’s tough to think much further into the future.

But then, if you survive the chaos, at some point in your journey, you cross a chasm, and life begins to feel calmer—even though your business is now larger and you have more people dependent on you and more responsibilities on your shoulders. 

It’s not always clear how to know you are making this transition, but I think I am going through it now. On one hand, life feels crazier than ever. MultiFunding, which I started in 2010, had a strong year last year, and our team has grown by almost 50 percent, which has created all kinds of growing pains. In addition, I am halfway through the first year of my two-year term as president of EO Philadelphia. And since October 7th, I have been helping lead a team of entrepreneurs supporting the EO chapter in Israel. The schedule is demanding and can feel utterly overwhelming at times.

And yet, despite all of this new chaos, life feels calmer than it did a few years ago. I am not sweating payroll every day. I can slow down on weekends. My office and team run fine—if not better—when I am not around. My travel schedule is less chaotic.

I can’t point to one thing that helped me get to this stage, although I think it has several components. One is simply grit. You must be willing to grind it out. The second is my ongoing determination to try and get myself fired—or to say this a different way, I am constantly trying to outsource and delegate work that I believe others can do better than I do. And finally, and perhaps most importantly, it’s about building a culture of trust and respect around you.

Part of me feels guilty about my new freedom. I catch myself wondering whether I’m doing something wrong. Should I be working harder? Am I missing out on an opportunity? Is it OK to slow down? My responsibility and primary goal in 2024 is to work through this transition. If I can keep pulling myself out of my day-to-day responsibilities, I’m confident I can empower my team, get physically healthier, and start taking more time for myself. At the same time, my goal is for my mind to become clearer and to focus more on creativity and strategy for my company.

I don’t think there is a formula for making this transition, and I don’t imagine it will proceed in a straight line. But I know I need to make changes in my personal and business life to succeed. For example, something clicked over dinner with my wife a few weeks ago. She stopped me from eating and encouraged me to give myself time to digest and enjoy my food. I don’t always take advice well, but this time I did, and of course, my wife was correct. Since that dinner, I have been diligent about eating slower, and that one small change is making a difference in my life.

I am trying to take the same approach in other parts of my life. I wrote a recent column about my efforts to outsource my email box, which is going well. I am overcoming the urge to keep up with hundreds of emails a day. I am less concerned that I will miss out on something big. And I am concentrating better on the stuff that matters.

The irony is that, by slowing down, I feel I am speeding up. And the engines around me that I am helping to navigate are running full speed ahead. The primary reason this is working is the team of exceptional people around me and the values of mutual trust and respect that we live by. I simply would not be able to cross this chasm without our people and our culture. And, perhaps more importantly, I also have to be willing to let go and let them take charge.  

It would be great to continue this balancing act over the next year. I am hoping to increase the impact of the non-profit groups I am involved with. Personally, I want to find more ways to lead a healthier lifestyle. And I want to continue with the business transformation, which will allow me to think more strategically and diversify the products we offer. I am hopeful that I will be able to make a big announcement soon.

Ami Kassar is CEO of MultiFunding.