Startup CEOs and Investors: Brian Weiss, Carebox

Startup CEOs and investors with strong writing and teaching skills are welcome to post their ongoing stories and lessons learned. Contact me if interested.

Delivering Opening Lines
By Brian Weiss

My name is Brian Weiss and I’m the founder of a healthcare IT startup.

I’ve got these really great ideas about how to make everyone healthier, solve healthcare data interoperability, enable payment reform, advance clinical research, leverage big data to fix the US healthcare systems, make the world a better place, and create a billion-dollar company. Oh, and did I mention it all runs in the cloud?

You’re not really buying that, are you? I don’t blame you. It’s not a very good opening line.

Opening Lines

I’ve spent much of the last few months delivering opening lines – to (potential) investors, team members, strategic partners, pilot customers, editors of healthcare IT publications with proper-capitalization fetishes …

It’s not like I’ve never delivered an opening line before I became a startup founder. In everything we all do, there’s always a first line, a first slide, an opening paragraph, a first impression, a useless abstract class at the top of the object model hierarchy (what, I’m the only former software engineer in the room?)

I’ve had to pitch ideas, sell things, present solutions, and introduce myself many hundreds of times. No, I haven’t ever written a column in a publication like HIStalk (is there even such a thing?) But I’ve delivered really bad opening lines countless times! I’m even experienced enough to know it’s not the end of the world. At various times in my past, I’ve somehow managed to get hired, promoted, selected in an RFP, invited back to a conference, and even married, despite being opening-line-challenged.

So why am I having such a hard time writing this column’s opening?

Matchmaker, Matchmaker, Make Me A Match …

Today, I’m attending a “Matchmaking Session” in New York as part of the ONC Market R&D Pilot Challenge. To help encourage innovation around some of its strategic priorities, ONC is sponsoring a contest that will select six winning pilot projects. Each pilot proposal has to be presented jointly by an innovator (an early-stage healthcare technology company) and a host (an established healthcare organization operating in a clinical environment). To help match up hosts and innovators, there are three of these matchmaking events taking place over the next few weeks.

If “matchmaking session” sounds like something from “Fiddler on the Roof,” you’re on the right track. The format here is speed dating for startups, commonly used at events that bring together startups and investors. I will have 13 minutes to woo my date(s).

They also sent me a colorful one-page tip sheet to help me prepare. It seems they think I will do a better job if I make an effort to have a clue in advance about the company I will be meeting with, make my presentation engaging, explain what I do, and say something about my team and business model. And, they suggested that I practice in advance.

I’m being a tad cynical about their tip sheet. I suppose it’s pretty good advice… for presentation beginners.

My Kindergarten Artwork

My memory from when I was five years old is probably flawed, but I think this is close to being a direct quote from my kindergarten teacher to my parents about my artwork: “Brian is trying hard and we don’t want to discourage him. The important thing is to keep at it.”

A couple of weeks ago, I was in a meeting with a senior executive at an important partner of ours. It was a preparation meeting in advance of a larger meeting she had coordinated in which I would be presenting my startup to other leaders at her company.

I showed her what I had prepared. In a very polite and cheerful way (curiously reminiscent of the disposition of my aforementioned kindergarten teacher), she told me (in not so many words) that what I had prepared for the meeting clearly showed I was trying hard and she didn’t want to discourage me, but the important thing was …

… to just say very concisely what the problem was we were trying to solve, what our solution was, why it was good for her company, why we could do a good job, and “then just show them the demo.”

I dusted off my ego, did my best to do exactly what she suggested, and I thought it went pretty well.

I’ve coached others with similar advice countless times. Why did I need to be told that now?

Introductory Presentations

Last week I had a call with the CMO of a very large healthcare organization, which I can barely allow myself to dream might one day be a partner of ours. The call lasted less than 15 minutes.

Just as I was concluding my build up to Slide 1, he said he was already on Slide 8 and asked me a couple of short questions. Then he told me it all looked pretty clear, sounded interesting, he would do some checking internally, and get back if they were interested in hearing more. He got back to me the next day about setting up a follow-up meeting to go into more detail. We’ll see where it goes.

I’ve done 10s of similar calls before that one. They run 30-60 minutes and my results generally weren’t as good. I now have a much better presentation than I had before and the obvious advice I got a few weeks ago was clearly something I needed to hear.

What’s Different/Special About That?

My column will only be worth reading if I have unique and valuable perspectives to share with you that emanate from the fact that I’m a healthcare IT startup CEO, not just some guy who has to get better at introductory presentations and opening lines.

Can I do that? I’m not really sure – and this might be a very short-lived column.

For now, I just want to share with you why (I think I’ve figures it out) I am now having experiences like the ones above that sound like something out of “my first days a junior salesman” – when I am quite certain I knew how to do an effective introductory presentation many, many years ago.

Starting Up Means Starting Over

Each step in our career generally lets us build on the previous ones. When I was EVP/SVP/pick-your-favorite-letterVP of products, my title, the company and organization I represented, the many people working for me, a ton of support infrastructure — all came through the front door with me.

But it’s even more than that.

Once you get your degree, you don’t have to pass your mid-term exams anymore. But could you if you had to? On the way to the where you are today in your career, you probably paid your dues on many rungs of the ladder. But could you go back and do a good job at each level again, now?

When you are given a new challenge today, is it really all that new? Or is it a natural evolution of what you do today that lets you relatively easily carry over your skills, expertise, experience, and credentials?

I’m no longer the exec who gives good advice to others about how to structure their presentations. I am the junior salesman getting better at making a pitch. I’m the guy at the ONC matchmaking event who needs the tip sheet. I’m the guy working on the template, the web site, the demo, the story. Everything I do starts with a blank piece of paper. I’m the guy who now needs the feedback that people who do that kind of stuff get.

The fact that I could do a good job presenting as a corporate exec doesn’t mean I can do a good job presenting in this context. The fact that I could give advice to others about the kinds of presentations I am now making doesn’t mean I don’t need to hear that advice myself from others, now.

Whatever I think I’ve learned or accomplished in my career to this point only matters if I can translate it into something concrete that helps me better do the stuff I need to do now. That’s always a true statement for all of us, but it takes on a whole new meaning when you have to do something that isn’t a natural evolution of what you did yesterday.

What Is This?

Two weeks ago, Mr. H put out a call for a "startup CEO or a venture capitalist who wants to share their keen insight and sharp writing skills with the world."His intent, I believe, is that this column provide interesting and different insights and perspectives for the many HIStalk readers who are employees in established companies and interested in getting an insider view of the world of healthcare startups.

I told him I qualified as, “A startup CEO who wants to share” and we could see about the rest.

The column I’m planning to write (exact frequency to be determined) will draw from both agendas – the healthcare IT topics we’re focusing on and the ups and downs of the stages in the growth (I hope) of a startup – with a special emphasis on where the two meet.

I’m a beginner column writer. I hope to not completely disappoint relative to Mr. H’s objectives. If you’re able to suggest topics, approaches, improvements, etc. that can help me do that – I’d be most grateful. You can write to me directly.

Brian Weiss is founder of Carebox.