2017 – Page 2 – Maybe I'm crazy

Will the Apple Watch be the king?

We have entered into a holding period, like the time in which all the boats wait for a lock to open, to go in get filled and move into the big sea. This period is here because the Apple Watch has moved into the “hype” picture. The 3 year technology product is shifting from a wearable for geeks to a wearable with “real” value. It is not there yet, but on it’s way. For years, the Apple Watch has been thrown to the side as a cool gadget with no real value, yet recently with the focus in healthcare and in research, Apple has shifted its value proposition to pushing the iwatch as “an ICU on your wrist.” It is positioned to be the end all, be all of devices to monitor, track, predict and diagnose you remotly.

As a technology nerd, BIG Apple fan, and healthcare entrepreneur, I do not buy all of this hype. I do not believe that the Apple Watch will be everything for everyone and do everything a doctor can do an more. I certainly see a place for wearables and the capability of the Apple Watch, but not sure I see it as a god-like end all be all. I say this now because over the past few weeks the conversations I have been having between investors has swayed from “your on to something with your wearable” to “you are going to get killed by the big guys.” While I understand the perspective in that I am not a big guy and do not have billions to throw at a product, I am still a strong believer that devices who will be successful will be specialized specifically in healthcare. The ones who will drive real value will be the ones that are focused on solving real problems.

There’s a Fork in My Pitch

Lessons, Startup

Over the past year, I have pitched at 5 different events to audiences totaling over 2000 people. I have spoken to many clinicians from top hospital systems and investors from leading venture organizations. I am not looking to brag nor ask for sympathy, simply I am looking to ask why haven’t I received more financial backing. Why are organizations not more willing to fight for what they believe in and put money where their mouth is. I simply have to wonder.

From the numerous events, conversations and news articles that my company has been featured in, I know that I have struck a true pain point that exists in so many people’s lives. This problem of dementia and caring for loved ones touches so many, yet we are still in the same place as we began this discussion with. I have been toying with this question for the past week, what is the missing link or links that I am not getting. Or is this just the way it works you pitch thousands of people and get no capital interest regardless of how real the problem is to those thousands.

The Inner Circle of Trust

Startup

You would think that in a city of 2.7 million people and over 4000 startups, that you would never run into the same people, yet I am beginning to piece together that this BIG city of Chicago is actually really small if you get on the inside. From all the networking events I have been going to, I have started to see the same people at each event. Not everyone is the same, yet there appear to be a group of people who seem to be more popular than others who keep showing up to the same events I am at. Once I realized this trend, I started targeting those people to network with. As such, I would do a quick pitch, answer some questions, get a few business cards, follow up the next day, and then hope for the best.

Long story short, I think I am doing something right. Tonight I was invited to this new angel group’s launch party. This group broke off of another angel group in Chicago and is made up of successful young guys who love to hang out, invest, shoot the shit and have a good time. The group is made up of a unique combination of people all under 40-years old who have been successful in their careers. The group consists of a wide array of professionals who are lawyers, consultants, entrepreneurs and people in insurance. Beyond the invitation to this party, I was pleasantly surprised that almost all the “popular” people I had been seeing and networking with at various events around town were at this invite-only launch party as well.

Step away from the micro and think about the macro

Lessons, Startup

As a designer, developer, and an entrepreneur, I am a detail-oriented, perfectionist. I obsess over the details of every design, line of code, or product. It is almost like I have an itch that I have to itch and if I don’t then it just bothers me beyond belief. This “perfect” vision that I have in my head drives me to keep pushing until I can accomplish it. By staying up all night or not shipping a product till every feature is working, I work till the last minute. With all this said, I still manage to stay level headed and focused on putting the pieces together, but it can be challenging.

Over the past few days, I have been faced with this challenge. Next week, I have a big investor pitch presentation and I have been reviewing each slide and its content for “perfection.” Additionally, not only have I been reviewing the deck I have had an investor also review it with me. He sees things differently than I do (as expected) and therefore picks and prods at certain elements. This has been challenging because I have already picked it apart myself to the last degree, then to have him do it again is quite frustrating. As with many presentations, its good to have a second eye and in this case is self inflicted as I asked him to help, but it is making me go crazy.

A day in the life

Startup

As I have made this transition, the question I continuously get from friends, family and prospective entrepreneurs is what is your day like. Before leaving my job I had this understanding that it was going to be busy and stressful but couldn’t really put it into words beyond that because I frankly just didn’t know. My girlfriend thought about it logically if you were working 80 hour weeks with 2 jobs then when you just work careband you will have more time to hang out. The reality is that’s not the case.

Just this morning as I am writing this, I looked at my calendar and I have 3 back to back meetings this morning and one more in the afternoon. What comes with this is the question, how do you ever get work done. And that question is a tough one. When looking at the to do list there are a hundred things to do, things that require my time, attention and focus, not just delegating to others. My strategy so far has been to bring my computer and a notepad with me everywhere I go and use my time between meetings and events wisely. With this I mean, working on the train, the bus, at local coffee shops for spurts of time 15 30 min. I have cut out the occasional social media browse or news article browse when I have a few extra down minutes. The other area of time is at night after the “work day”. I usually spend that time working and doing the things I need to do to move the company forward.

Take time for yourself

Startup

I had a great week, not just because I am starting to feel situated but because I took a trip to Denver, CO. One of the things I had told myself before I joined my company full time was that I was going to take me the trip as soon as I left my previous job. Unfortunately, I couldn’t get the details situated fast enough so had to do it this past week instead. I had decided to take a trip to Denver, CO to climb some mountains and clear my head. Also, a good friend of mine whom I started my first company with in college lives out there, which gave me a chance to spend some time with him and a free place to stay. My goal in going to Denver was to take a break. To help me close the chapter of my past job and start the new chapter of this journey of my company. I was hoping I could just get away from the city and surround myself in nature in order to refocus and energize myself for the coming year.

On the plane to Denver, I was fortunate to sit in the middle seat on a Southwest flight. Many people would dread sitting in the middle seat, but I love to sit there. I also am different than most as I love to talk to the people around me. It is a game to me to see how long it takes me to get my neighbor to open up and tell me their story. It is also an opportunity for me to be who ever I want to be. Because the chances are you will never see that person again, you have this rare chance to live your dream or make up a few details in your current life. (I once convinced someone that I worked for google, because I was flying from San Fran to Chicago wearing a google shirt. That was a fun conversation. I can talk about this weird interest of mine for hours, and may in another post.) On this occasion though, I didn’t fill in any details and just told my story. Most of the time though I end up just listening and asking questions to learn about their stories as I did this time with Ruth.

Getting Organized

Startup

In an effort to transition smoothly from my fulltime job to working for myself (my company), my advisor suggested reading The First 90 Days. The First 90 Days is a book for people (mainly executives) transitioning into new leadership positions to help them quickly and efficiently “prove their worth” to a company. Although, a little different for my situation I hope to take the techniques and strategies and apply them to my role as CEO of my company. One of the first chapters talks about how each month of your plan should have a specific goal or outcome. For me, I have made month 1 (August) all about getting organized. Without a clear roadmap or known framework of getting organized, I set out to create my own roadmap. Ironically, the timing is similar to how freshmen in college start their university experiences in August. I hope to apply similar steps as I did when I was a freshman in terms of meeting people, getting into a routine, completing homework on time, and many other important areas.

Ruth at Paperback Trading Company

People

At first I didn’t remember that southwest had open seating, but I embraced the opportunity to pick my seat when I got on. Being in the last group to board, I knew that I would have the opportunity to pick my seat, so I looked around and found the most interesting looking, friendly looking person (with my limited options) and sat down. I knew like with most plane rides that I had to figure out my neighbors story so as the plane started moving I started talking and we didn’t stop till the wheels came out to land, 3 short hours later.

Here is the story of Ruth: The Chicago native, book store owner, cat lady, best grandmother to her only grandson, letter writer, and lady who believes love and respect to all is the way to a happy and good life.

I cannot decide between two women

Startup

People constantly ask, usually with a bit of shock, how I could possibly do such a thing. A nice, trustworthy, honest guy, sneaking around, splitting my time between not one, but two women, and keeping it up for more than a year! My short answer is that I love each one for different reasons and I see a future with both – their interests and passions directly line up with mine. When I am spending time with each one, I feel empowered and confident enough to accomplish anything. I know that I will have to choose at some point. I’ll have to make up my mind and go full force with one while leaving the other behind. The conversation will be difficult; to discuss all we’ve been through and why I have to move forward with my other love… and if it’s even possible, to break up on good terms.