Week 14 at Dreamit is in the books and the finish line is in sight

As I sit in my home and write this, the calendar silently ticks over from Friday evening to Saturday morning. It is 12:30 A.M. and it seems these are the normal hours I’ve been keeping as I work to prepare Kermit, my digital health startup, for our fundraising roadshow. The house is completely quiet, except for an occasional visit by a solid black cat who can’t understand what I’m doing up. She’s thinking maybe she can coax a snack out of me at this hour.

Since the passing of my father 14 years ago, I vowed that I would not work more than necessary, would not keep long hours that created stress or punished my body, would change the way I ate and would be commited to a lifestyle of fitness. My father was a cardiologist and he certainly placed a high value on his work and his patients. The end of his life came much more quickly than any of us anticipated — and I’m sure much more quickly than he had planned at a young 63 years of age. Watching him pass in a hospital bed, I made an internal vow that work would never take precedent over my family or my health…ever.

But Dreamit, the digital health accelerator we’re participating in, has been demanding. I’m not one to do things halfway and I knew going into this that I would do it to the best of my ability and make a great showing that would put Kermit in the best possible light or not do it at all.

Twelve weeks ago, the founders from 25 Dreamit companies stood around a campfire and, one-by-one, confessed what they feared the most about the next three months ahead. There must have been almost 100 people circled around that fire pit and many of the responses were expected and similar. Most were, I felt, honest confessions of young entrepreneurs embarking on something they had only read about in blogs or seen others go through. The very last to go was a CEO about my age named Dan. It took a while to get through all of the responses and when it came time for Dan to take his turn, there was a pause…then he took a breath and waited even longer…then, with all the courage he could muster after a full day of seminars, breakout sessions, liesure activities and soul-searching, Dan said the following in a gentle voice, “What I fear the most is not being able to spend time with my wife and children — with my family”.

It was quiet — an eerie kind of quiet. Did this man just break the cardinal rule of startup life by putting family ahead of the work mission? A tear began to well up in my eye as I thought of my own family only a few hours away from the wooded mountains of the Destination Dreamit retreat in Pennsylvania. Dan’s family, however, was a world away in Israel.

I received a word of wisdom from a senior director at Independence Blue Cross who was sitting in as a guest today during my pitch rehearsal. He commended me on a great pitch and asked how the Dreamit program had gone for me thus far. I admitted, honestly, that I was tired and it has been a lot of work. I’ve really tried to balance preparing for the investment round with running the business, selling, negotiating deals and editing contracts and family life. He reminded me that there is a difference between a mid-life executive and a grad student CEO. He quipped, “It’s great you have the experience, but you have to work harder because you certainly have more to manage”.

All in all, I would not have traded these last fourteen weeks to try and accomplish this on my own. Accelerators, although becoming quite prolific, definitely provide value when executed correctly. And Dreamit offered something that was important to me. One of the reasons I chose Dreamit over other accelerators we were considering was that after the initial two-week onsite in Philadelphia for the customer immersions, we were allowed to complete the remainder of the program from our home office. And although I’m working late nights, skipping afternoon workouts and morning runs to stay on schedule, I’m with my family. I hope Dan has had the same experience.

The next two days will provide a brief weekend of rest and an chance to put the finishing touches on the pitch deck and do a little more research on the partners at the VC firms we’re meeting with and then it is time for the capstone event of Dreamit; the investor roadshow. I have to credit my wife and kids. They have shuffled around their early summer schedules and work duties so that I can hit the road for the next two weeks. I’m not a traveling executive — I don’t travel well and my family usually doesn’t exactly thrive while I’m away (I’m the food shopper and the cook of the family). So two weeks away is a big ask.

Nevertheless, I’m excited to show the Silicon Valley, San Francisco, Boston and New York what we’ve built and how we’re solving a big problem that has plagued hospitals for almost 50 years. I want others to get excited about what we’re doing and I think that they will. We’re going to get a shot at some of the best investors in health IT and SaaS and I couldn’t be more enthusiastic about our chances. There is no doubt in my mind that Kermit is going to the next level.

Kermit went into Dreamit as a strong offering. It has weathered 14 of the 16-week program with grace and has emerged with larger muscles and a stronger heart because of this pressure cooker called a digital health accelerator. Not everything was perfect, but it served us well and we could not have acheived all that we did in a short period of time trying to do this on our own.

Now, on with the (road) show.