Tag: Entrustet

My Entrepreneurial Journey

Note: I wrote this post back in May 2010 for a guest post on a large tech blog, but it never got used.  I found it today while going through my inbox and decided it was too good to not post.  This is my entrepreneurial journey from 2004 until May 2010.

As I made my way from Milwaukee, WI to Madison, WI for my freshman year of college in fall 2004, I had no idea what I wanted to do with my life.  I’d know for awhile that I liked working for myself: I’d been a soccer referee since I was 12, which allowed me to make my own hours and make more money than any 12 year old should be able to earn.  I’d been fairly bored with high school because we learned boring theories instead of practical ideas that would help me later in life.  My biggest take away from high school was “more practice, less theory.”

All of these thoughts took a backseat in my 18 year old mind when I received a letter from the University of Wisconsin notifying me that I’d lost the student football ticket lottery.  I was devastated.

After moving in, I’d been thinking about how to find tickets, but I didn’t have to look very far.  One of my friends invited me to a party my first night at college.  I was about ready to call it a night and walk home when I heard a guy screaming into his cell phone.  He hung up and was so mad that he slammed his phone on the ground, breaking it.  He got even angrier because he said he didn’t have the money to get a new cell phone.

Something in my brain just clicked and I said, “hey, do you have football tickets?”  He looked at me really strangely, but said he did.  I responded, “well I don’t have them, but I’d buy you a new phone for your tickets.”  I wasn’t really expecting anything, other than maybe some choice words, but to my surprise, he got excited.   The next day, I tracked the broken cell phone guy down via a friend in the frat, bought him the money for the phone and made the exchange.

I was pretty excited.  It only took me one night to get my football tickets.  All was right in the world.  I told my story to some of my new friends and quickly realized that there were a ton of kids who were in my same predicament.  I agreed to help them find tickets.  It pays to be in the right place at the right time.

Enter Exchangehut.  I first remember seeing flyers and spray paint stencils for the site a week into my freshman year.  I checked it out, signed up and was user number 1117.  Exchangehut was a ticket exchange that worked like the stock market.  Buyers could input a bid price and sellers could put in an ask price, creating the market.  When the prices matched up, a sale happened and both parties were contacted.  I used the site to help 4-5 friends buy tickets and quickly saw how useful the site was.

As the year went on, I became one of the more active users, I realized that the site had limitations and thought about creating a competitor.  I wrote up a simple business plan, but got discouraged because I was having trouble finding a programmer to write the new site.  I put the project on the back burner and went on with my summer.

I was in the right place at the right time again a month later.  The owner of Exchangehut was selling the site via an auction because he was graduating.  I quickly shot an email back, did my research and put in a bid.  I excitedly talked with my friends about how I was buying a business and to my surprise, one of my best friends from high school said he was too.  I said “what business” and we both said “exchangehut” at the same time.  He was a computer engineering major and we decided to merge our bids.  A month later, we were the proud owners of a 2000 person tickets and textbooks website at age 19.

We ran the site until 2008, growing the site to 150k users across 8 college campuses.  We learned a ton and needless to say, I was hooked.  I loved coming up with ideas for the site, promoting the brand and working my own hours.  I was making more money each week working on average 8 hours per week than my roommates were making bartending and waiting tables full time.  I loved the freedom that came with being able to work from anywhere.  I got to travel places and meet interesting, creative people.  I enjoyed meeting people who though “how can we fix a problem” not “why can’t we.” We sold the business to our ad network in summer 2008, but I knew I was going to start a new business.  This isn’t to say it was easy.  We put in long hours, answered angry customer emails and calls and continued to go to class.

Like many entrepreneurs I know, I keep a business idea list.  I had over 200 ideas on my list and after selling, worked on cutting them down to 10 that I thought were promising and would be fun to work on.  All that stopped when three professors I had gotten to know independently told me that I had to meet a student named Jesse Davis.  At the same time, two of my friends said that Jesse was working on something cool and needed a partner.

I met Jesse in one of the libraries on campus and he pitched me his idea.  Jesse’s pitch went something like this:

“I just read Thomas Friedman’s The World is Flat and couldn’t get through it when I got to US Marine Justin Ellsworth’s story.  He was killed in action in Iraq and his family wanted access to his Yahoo! email account.  Yahoo said no.

After a long court battle, a judge ordered Yahoo! to turn over the contents of his email accounts to his parents.   It shouldn’t take months to gain access to a deceased person’s email account.  Also, what if I don’t want my parents looking into my Facebook account or other sites I might have? Friedman ends the passage by saying “someone sort this out.”  Let’s create a system for people to store their last wishes for their digital assets, which are any online account or file on their computer, and let’s allow them to input their passwords so that their survivors have access.

I immediately thought back to ExchangeHut.  In 2005, we hired a programmer to help us make improvements with the site and at one point, I realized that our programmer has all of the usernames and passwords to the server, database, credit card processing, affiliate programs and everything else that was necessary to run the site.   Like programmers like to do, he used a random password generator, so there would be no way we’d be able to guess his passwords if he were to get hit by the proverbial bus.  We ended up having our programmer write down every password on a piece of paper and I stored it in our safe deposit box, just in case.  Jesse’s idea would have solved this problem.

I was looking for a project, Jesse was looking for a cofounder with some experience and we hit it off.  Two months later, we founded Entrustet.

I was sold on Entrustet because we had a chance to create a solution a real life problem.  The death of a loved one is an incredibly stressful time and we thought we could help give people peace of mind that their digital assets would be dealt with according to their wishes, and that survivors wouldn’t have the burden of having to guess what the deceased person wanted done with their online accounts.

We’ve been working on Entrustet since November of 2008 and launched in March 2010.  In our first year, we spent under $20k starting the business.  We were able to spend so little because we hustled and were located in Madison.  We’ve stayed in Madison, even though we’ve had opportunities to move to Silicon Valley, New York, Boston or Austin.  Being located in the Midwest has given us some advantages that are often overlooked by people on the coasts.

It’s incredibly cheap to live and work in Madison.  Our office is located across the street from the state capital and we pay $200 per month.  I pay $400 per month to live in a nice apartment four blocks from the office.  On the coasts, we’d have had to pay 5-10x more.  While the talent pool is not as deep, we’ve found talented employees who cost a fraction of what they would on the coasts.

Madison is small enough that we’re able to get in contact with anyone we want to relatively easily and Madison has groups like MERLIN Mentors that help new startups by pairing founders with successful entrepreneurs who server as in informal board of advisers. Everyone in our company walks to work and we’ve become active in the startup community by starting Capital Entrepreneurs, a founders group with over 60 tech companies in the Madison area.

I’m a huge believer is pursing your passion and starting starups has allowed me to pursue mine.

The Whiteboard Desk

When people come to our office for the first time, they almost always comment on our desks and tables.    Ever since we moved in two years ago, we covered all of the available surfaces in white boards.  I love being able to sit at our big table and just write things down on the table as I think of them.  It’s great for taking notes on phone calls and writing todo lists.  It’s certainly helped increase my productivity and it was super cheap to set up.

We went to home depot and bought two 8×4 foot tile boards for a total of $20.  We had the guys at Home Depot cut our boards into our desks’ dimensions and taped them down with double sided tape.  It was a cheap investment that’s been a unique addition to our office.  Check out some pictures:

Do you have anything unique in your office that helps you work better or more efficiently?

Happy Two Year Anniversary Capital Entrepreneurs

It’s been two years since I started Capital Entrepreneurs, an organization to help Madison entrepreneurs connect. I’ve been blown away by how fast CE has grown and how quickly time has gone by.  On our two year anniversary, here’s the story of how we got to where we are today.

In April 2009, I was a month short of gruduating from UW.  I had just started my second company, Entrustet, with my business partner Jesse Davis.  Many of our friends were taking jobs outside of Madison and the two of us were going to be staying in Madison to startup Entrustet.  We both had been a part of the UW entrepreneur scene and had received support from other students, professors and the university itself, but since we were graduating, we were worried that we would not be able to take advantage of the support system any more.

I realized that most people make new friends after college via their job, but since Jesse and I were the only people in our company, I worried that we’d get isolated.  I knew that there were other founders in town who were graduating who likely felt the same and wanted to do something make us more like coworkers, even though we were all working on separate businesses.

I’d been to most of the startup focused meetups and events around town and thought that there was a niche for a group that was specifically for founders that could compliment the existing networking events like High Tech Happy Hour and Madison Magnet.  I wanted to create a place where founders could get to know each other, hang out and talk freely about their problems, dreams and goals, without having to worry about getting pitched by attorneys, insurance agents, accounts or the press.  I wanted a place where ideas flowed freely and entrepreneurs would feel comfortable both asking for help.  I wanted it to be free and without structure.  I wanted Madison’s entrepreneurs to be a community of friends, not a disparate group of people who just happened to start companies.

At the end of April, I talked to a few of my entrepreneur friends and asked them what they thought.  Everyone loved the idea, so I started to look for a venue that would give us a private space for free, along with some other enticement to get our business.  Our friends at Brocach gave us a space in their upstairs bar, along with a nice food special and we set our first meeting.  I invited all of my friends who met two simple rules.  They were:

  1. The founder or first employee of a Madison business
  2. Were not a service provider like an attorney, accountant, insurance agent

Our first meeting was right before graudation in May 2009.  Around 10 founders showed up.  We introduced ourselves, had beers and talked.  It was great.  We decided to do a second meeting that next month.  I quickly realized that Madison entrepreneurs were doing some amazing things, but that the rest of the community had no idea.  So I started a website.  It’s a simple blog that gets updates whenever a CE company gets press, sends out a press release or the city itself makes news.  It also includes a list of member companies, resources for Madison’s startups, along with info on how to join.

Since May 2009, CE has grown slowly, but surely each month.  The second meeting had 12 founders, the 4th 17.  It just kept growing.  One year later, CE had 34 member companies and 60 registered members.  As we grew, service providers wanted to attend to meet the entrepreneurs.  We decided service providers could sponsor CE and attend ONE meeting per year.  At that meeting, they are not allowed to sell their services, just answer questions and get to know the entrepreneurs.  They also have to pay for our bar tab.

We were lucky enough that Neider and Boucher, Michael Best, Boardman Law Firm, Marquette Golden Angels and Venture Investors agreed to be our first sponsors.  Sponsorship worked out great for CE and the sponsors.  It was a great way for entrepreneurs to get to know service providers and for the service providers to get to know us.  It was also a great way to attract new, high growth clients.

CE continued to grow, but I was a little worried when Jesse and I got selected for the Startup Chile programForrest Woolworth stepped up and ran CE while I was gone and did an amazing job.  Over the last year and especially in the last six months, CE has started to take off.  We now have over 75 member companies and 120 people on the email list.  We’ve been featured in Techcrunch, Read Write Web, Madison Magazine and tons of other publications.

Member companies have been featured in the NY Times, The Economist, Financial Times, Wall Street Journal, Techcrunch, Mashabale, Forbes, BBC and hundreds of other influential blogs, newspapers and magazines.  CE companies have created over 300 full and part time jobs during one of the worst economies in recent history.  We’ve raise over $15m in funding.  Spinback, founded by CE alumni Andrew Ferenci and Corey Capasso, was acquired.  Spill, founded by CE alum Heidi Allstop was selected for Techstars.  My company, Entrustet, was selected for Startup Chile.  CE members have been instrumental in helping start the Forward Technology Conference, Build Madison and other entrepreneurship initiatives in Madison.

Madison’s startup scene has grown significantly in the past few years and I’m excited and proud that CE has been a part of it.  I can’t wait to see what the Madison startup scene looks like in another year!  I’d like to thank everyone who’s helped make Capital Entrepreneurs what it is today.  It would never have been a success without all of your help!

How to Live Before You Die: What I’ve Learned From Entrustet

At the end of the segment on NPR’s Forum yesterday, the host asked me if my life or worldview has changed at all since starting a death-focused company.  I deal with death on a regular basis.  It’s forced me to confront many issues of mortality and the unpleasantness that goes along with thinking about my own demise.  I’m thankful that I’ve had the opportunity to think about issues that most people only think about in their 50s or even potentially on their death beds.

So how has working in the “digital death” industry changed me and my worldview?

I no longer take anything for granted.  I’ve read so many stories of people dying unexpectedly that I’ve realized how special life truly is.  Jesse will say from time to time “Isn’t it ridiculous that we’re alive?  Think about all of the things that had to go right for us to be here today. It’s amazing.”  It really is true.

If the average life expectancy is 80 these days, it means we only have 29,200 days on this Earth.  Before Entrustet, sometimes I thought days were boring, or were simply impediments in time before I got to do something I really wanted to do.  Now that I’ve been working on Entrustet for almost two years, I never take a single day for granted.  It’s one of my 29,200, and only if I’m lucky.

Dealing with death has caused me to care even less about what other people think.  You only live once, so do what makes you happy.  In the whole scheme of things, rejection isn’t that big of a deal.  Seize your opportunities and take your chances with alacrity.  You never know when you won’t have the ability to take them in the future.

I’ve become even less materialistic.  You can’t take your possessions or your money with you when you die, so I’ve come to realize that I don’t need things or to make $1b (unless we get hyper inflation!).  When I read about people on their deathbeds, they all say they regret not spending more time with friends and family or taking a trip to a foreign country or taking the opportunity to work on the things they loved.  They never say they wished they had bought a bigger TV or a nicer car.  I’ve realized that it truly doesn’t take much (money) for me to be happy.  I know I can live well on a small amount of money.

It’s strange that I’m dealing with these issues as a 25 year old, but I think I’m lucky.  Most people push the idea of death down the road and many people don’t end up following their dreams.  I’m glad I’m realizing these truths now, not when I’m 50, 90 or not at all.  Sometimes it takes a near death experience, but for me, all it’s taken is being near death.

Please watch Steve Jobs’ speech to Stanford’s graduation class.  Jobs was diagnosed with an extremely deadly type of cancer and miraculously survived.  He’s an authority on how to live before you die and his speech is where I got the title for my post.  Do yourself a favor and take the time to watch.  You only live once, make the most of it!