Entrepreneur by Accident

I’ve been on my own” professionally for almost 12 years now. It’s still crazy that it all really happened by accident.

In the Spring of 2005, I decided to change jobs after a rewarding stint at Musictoday. Musictoday was my first start-up experience, but it wasn’t as small as the company I was going to work for. That company had less than 10 employees and I was going to lead an eCommerce division that only included one person, me.

I took a long weekend in between jobs. My wife and I visited the Homestead resort and that’s when I received the call. The CEO of the company that I was going to work told me that the owner has decided to shut down their eCommerce line of business. Therefore, I was without a job. I was a little taken aback, to say the least.

Thankfully, I left Musictoday on good terms. Luckily, they had yet to fill my position. I didn’t want to go back full-time though. So, I decided to freelance as a Project Manager/Business Analyst. I picked up a couple other gigs and liked it. Specifically, I liked the freedom and the variety of work. I also enjoyed the chase for new business.

Over the course of the next 12 months, I freelanced and also interviewed for jobs. I received one offer that was really hard to turn down. I also was helping my wife go through some very difficult family issues. It was a period of transition that finally ended during the second half of 2006 when I decided to fully focus on starting a business.

I never thought too seriously about starting my own business. I never felt a burning desire to become an entrepreneur. I’m not sure I would even be in this position if it wasn’t for those series of events in 2005. However, it taught me one of the most important lessons of entrepreneurship: how to transform a setback into opportunity.

14 February 2017
Entrepreneurship Life

My 2016 Homescreen

M.G. Siegler has been posting his home screen every year on the last day of the year for the past 4 years. It is a simple look into one person’s current app usage, which I find interesting given his deep tech experience.

So I figured I would do something similar, but with a slight difference. Below I’ve posted my home screen as of the first of the year, after I spent some time reorganzing apps based on previous usage and potential usage in 2017. You could say that my homescreen reflects some things I want to change in the new year.

My 2017 HomescreenMy 2017 Homescreen

The apps that have occupied a space on my homescreen for awhile now, which I doubt will be replaced this year are Calendar, Dark Sky, Phone, 1Passowrd, Maps, Safari, Messages, Photos, Slack, and Camera.

I’ve tried to organize the rows to the best I can. The third row contains my news consumption apps. ESPN is the only one that has been a constant. The other three are recent additions to the homescreen. I started listening to more podcasts last year, subscribed to the New York Times, and revived my usage of Instapaper.

The fourth row is my work row. Slack, Asana, and Harvest are staples, but HubSpot is new. We are using it as our CRM right now although I have had a history of changing CRM platforms, so we will see if it lasts the year on the homescreen.

The last two rows are organized in a way that is designed to produce content. When I glance at my phone, the apps on the right side of the screen stand out for me. Thus, I’ve organized these rows so that the app on the far right kicks off a process that is followed by each app to the left. For example, this blog is powered by Blot. I write posts in Byword and then save each one to Dropbox, which will automically publish the post to this blog. Safari is to the left of Dropbox, so I can view the post in a browser and then tweet it out using Tweetbot (my Twitter app of choice). The last row is similarly designed. After taking a photo, I use Camera+ to edit the photo (sometimes), and post it to Instagram (if it’s worthy). Making a return to not just my homescreen, but my phone, is Tumblr since I am using it for a 365 project. The plan is to post one photo a day to Tumblr.

The money row is filled with my two most used music apps - Amazon Music and Sonos, the Photos app, and Messages.

The only other apps that are relatively new to my homescreen are Airmail, Notes, and Lifesum. Airmail is my current email app, but it’s on shaky ground. It’s a bit slower than other mail apps, and I just might go back to the native mail app. Now that you can share Notes with others, this is the app that my wife and I use to share lists and notes. I’ll be shocked if that leaves my homescreen. Lifesum is my health/diet app. My relationship with Lifesum is on again/off again. Since it’s the first of the year, it’s on again. Hopefully it will stay on my homescreen.

What does your homescreen look like? Do you have any apps that you recommend?

2 January 2017

My 2016 in Live Music

Time again for my annual musical nerd post. After a stellar 2015, this year was a bit of a letdown. I saw 25 acts this year, down from 30 in 2015. I did see quite a few acts for the first time in 2016, but only one blew me away. Most disappointing though is that I only caught one show in a new venue (new to me). Oh well, here is to a better 2017!

Below is a list of the musicians that I saw live in 2016 with favorites in bold.

Lockn’ 2016Lockn’ 2016

  • Zoso— 1/14, The Jefferson, Charlottesville VA
  • Heartless Bastards — 02/28, The Southern, Charlottesville VA
  • Yo La Tengo— 03/27, The Jefferson, Charlottesville VA
  • White Denim— 04/19, The Southern, Charlottesville VA
  • We Are Scientists — 05/15, The Southern, Charlottesville VA
  • Lake Street Dive — 06/11, Charlottesville Pavilion, Charlottesville VA
  • Tony Furtado — 07/03, Eddie’s Attic, Decatur, GA
  • Joe Russo’s Almost Dead— 08/25, Lockn’ Music Festival, Arrington VA
  • Vulfpeck — 08/26, Lockn’ Music Festival, Arrington VA
  • White Denim — 08/26, Lockn’ Music Festival, Arrington VA
  • Charles Bradley & His Extraordinares — 08/26, Lockn’ Music Festival, Arrington VA
  • Peter Wolf — 08/26, Lockn’ Music Festival, Arrington VA
  • Ween — 08/26, Lockn’ Music Festival, Arrington VA
  • Phish — 08/26, Lockn’ Music Festival, Arrington VA
  • Keller Williams Grateful Grass — 08/27, Lockn’ Music Festival, Arrington VA
  • Twiddle — 08/28, Lockn’ Music Festival, Arrington VA
  • The Wailers — 08/28, Lockn’ Music Festival, Arrington VA
  • Chris Robinson Brotherhood — 08/28, Lockn’ Music Festival, Arrington VA
  • Phil Lesh & Friends — 08/28, Lockn’ Music Festival, Arrington VA
  • Gary Clark Jr. — 08/28, Lockn’ Music Festival, Arrington VA
  • Phish — 08/28, Lockn’ Music Festival, Arrington VA
  • Real Estate— 09/29, The Jefferson, Charlottesville VA
  • Chris Robinson Brotherhood— 11/10, The Jefferson, Charlottesville VA
  • The South Carolina Broadcasters— 11/19, Cville Coffee, Charlottesville VA
  • Driftwood — 11/19, The Southern, Charlottesville VA
31 December 2016
Music Lists

Why Rogue One’ Is a Better Star Wars’ Movie Than The Force Awakens’

In other words, Rogue One contains more Star Wars head nods, hat tips and hidden treasures than an eight-year-old’s toy collection and a San Diego Comic-Con exhibit hall combined. So why is it, then, that the film somehow feels fresher than The Force Awakens’ nostalgia?

Warning: Spoilers in the article linked above and my thoughts below.

I loved TFA, but if it were not for the new characters, the film would have been disappointing due to its all too familiar story. Rogue One is a very familiar story of course, but it’s told from a new perspective with an atypical ending and that is why it’s better.

I can see why some compare the tone of Rogue One to Empire, but it more closely aligns to Revenge of the Sith. While the Rebels didn’t win one battle in Empire, no major characters died.

Of course, Empire is still the best movie in the franchise, but Rogue One is clearly the best prequel, just for that final Vader scene alone. That’s the Vader we were all hoping to see in ROTS.

20 December 2016


There is a simple message that keeps popping up in my life over the last few weeks. It’s become a source of motivation and an answer to occasional thoughts of doubt, negativity, and just feeling overwhelmed.

No matter what, always be on the offensive.

Throughout my life, I’ve had a habit to go with the flow. I’m not afraid of confrontation or stand for what I believe in. I often do in business. But, I’m also content to sit back and let others drive decisions if I sense that my opinion or viewpoint could ruffle someone else’s feathers, especially in matters that don’t pertain to my business.

That kind of attitude often puts me and my family on the defensive.

It’s come up in my family’s volunteer efforts. My wife and I can continue to sit back and be assigned tasks that might overwhelm us or we can speak up and take on what we know we can deliver while also making the scope of our request clear so we do not over commit or be taken advantage of.

It’s come up in the precious time together as a family. We have been taken on some wonderful vacations thanks to the grandparents. Week long beach vacations in the Carolinas, Disney World and the Mickey boat to name a few. With three kids under the age of 10, it’s tough to do more than that for a variety of reasons, mostly financial and time off from work. Of course, that’s the easy way out. You only live once, right? Before you know it our kids will be off to college and we will regret not taking them to more places. Again, it’s a matter of going on the offensive and making it happen regardless of the hurdles.

And then there is my business. It takes a toll on me, but I love it. The peaks and valleys throughout the years have given me a lot of grey hairs. Every time we hit a valley, it’s a stressful period. We keep bouncing back by going on the offensive, but maybe we should be doing even more.

I recently saw John Bassett III, CEO of Vaughn-Bassett furniture speak at the University of Virginia and subsequently have been reading his book, Making It In America. Mr. Bassett and his family have been in the furniture business for generations. While all his competitors were selling out to the Chinese in the early 2000s, Mr. Bassett and his team held their ground and keep producing their furniture in America … and were successful. But they didn’t hunker down during this crisis, they went on the offensive by investing in new ideas and programs, which led to higher revenues, incentivized workers, and improved production.

As I get older, I am starting to feel time ticking away like never before. Sitting back is not a way to live life to the fullest no matter what the situation. Go after it every day like it’s your last.

2 August 2016


My son on the high diveMy son on the high dive

I love the month of August. It’s a transformative time on the calendar as the dog days of summer wind down and give way to fall.

On August 1st, I’m in the thick of a summer haze. It’s miserably hot, but that means I’m at the pool almost every day. August is the time for that last summer getaway; the last chance to attend a music festival or a larger-than-life stadium show. It’s the month typically reserved for that 10 game west coast swing, which could kill your baseball team’s playoff chances. If you’ve been golfing all summer, August usually produces the best round of the year. August makes me think of Maine. I love Maine.

But as August moves on, an excitement of a different sort builds. Friends, neighbors, and colleagues all return home after that last summer road trip. It’s good to see them, catch up and make plans for the fall. It’s back to school and whether you are a teacher, student, or parent, it always symbolizes a new start. After one of the slowest stretches of the year, work finally returns to a normal pace because everyone is back at the office.

August begins in a stupor that slowly wears off as the days pass by. At the end of month, that stupor has been replaced with a sense of purpose, optimism, self-motivation and focus to get busy again.

It’s this transformation that makes August the best month of the year. I can’t wait to experience it again, but first things first.

See you at the pool.

1 August 2016

It’s The End of The Laptop As I Know It (And I Feel Fine)

About one month ago, I purchased my 4th iPad. The first 3 didn’t go so well. I still own the first 2 (1st Gen iPad and the 1st Gen iPad mini), but they belong to my kids and have for years. About a year ago, I thought I could use an iPad Air for work to go along with my MacBook. That didn’t work out too well either. I stopped using it after a couple weeks. I sold it after a couple months.

Why the hell would I buy another iPad?

One reason and probably the main one is that I’m a sucker for gadgets, specifically Apple devices. I’ve owned at least a half dozen iPhones and Apple TVs over the years. I also own an Apple Watch (at least I waited over 6 months after its release to purchase it). I wanted to try the iPad Pro.

The other reason is I wanted to try to replace my laptop with a tablet. That was never my motivation when purchasing the previous iPads. Regardless, I was fully aware that I could be returning it within the 30 day policy. I was hopeful, but realistic.

Before I dive into the result of my first 30 days, I should explain what I do for a living, which will explain what I use a computer for. I’m the co-owner of the digital and branding company, Storyware, in charge of Sales & Operations. Our team currently consists of 5 people, so we all wear a lot of hats. Occasionally I would roll my sleeves up for some very basic front-end development or use PhotoShop.

During the last 6 months though, my business partner and I decided that I won’t be writing code or pushing pixels around anymore unless it’s an absolute emergency. I need to focus on my day job — selling and running the non-technical side of our business. Thus, I use a lot of communication, documentation, and productivity applications. So when the time came for a new laptop, I decided to take the plunge and buy the 9.7 inch iPad Pro with the Apple keyboard and Pencil.

Now I don’t plan to use the iPad Pro as my only computing device. I still have a Mac, in fact two, but they are rather old machines. I will be using a 2010 Mac mini at the office. It’s getting a new hard drive, which will be nice. I also have a 2010 11 inch MacBook Air at home. However, I am giving it to my kids. I only plan on using it in case of an emergency.

When I purchased the tablet I envisioned using the desktop as my primary device at the office and the iPad Pro as my primary device away from the office. This is no small change. As a small business owner, I used my laptop a lot away from the office — including almost every night.

What has happened though is more than I expected. When given the choice of the desktop or tablet at the office, I prefer the iPad Pro. I do use both at the office, but I expected the tablet would be in the bag in favor of the desktop. Now it’s the first device I boot up each morning. The iPad Pro has become my primary computing device, rather quickly.

Why now though? How is the 4th time a charm?

It’s the keyboard and the pencil, without a doubt. I was very skeptical when I bought the Apple keyboard. In fact, I almost didn’t buy it, but I figured I could return it. The exact opposite has happened. I love it. The iPad Pro keyboard just feels natural to me, which was a surprising development. I made a lot more fat-finger mistakes on my last laptop, a 12 inch MacBook, than I do with the iPad Pro keyboard.

The Apple Pencil definitely lives up to the hype. I was more excited about that purchase than the keyboard and it has not let me down. I have only used it with one app on a regular basis (GoodNotes), but it has been flawless.

So, my 30-day trial has ended and I am fully committed to using the iPad Pro as my primary computing device. It feels different, fun, and odd at the same time. Most of all, it feels powerful. It is the first device that meets my computing and entertainment needs. I like that feeling a lot.

12 May 2016

My 2015 in Live Music

2015 was one of my best years ever when it came to seeing live music. Here is a rundown of whom I saw, with my favorites in bold.

All Good Festival 2015All Good Festival 2015

  • Chris Forsyth and the Solar Motel Band — 1/3, Union Arts & Manufacturing, Washington D.C.
  • Umphreys McGee — 2/11, The Jefferson, Charlottesville VA
  • TAUK — 2/11, The Southern, Charlottesville VA
  • The War on Drugs — 3/29, The National, Richmond VA
  • Delta Spirit — 4/11, The Jefferson, Charlottesville VA
  • Avers — 4/17, The Southern, Charlottesville VA
  • Futurebirds — 4/17, The Southern, Charlottesville VA
  • Ryan Adams — 5/3, nTelos Wireless Pavilion, Charlottesville VA
  • Beck — 5/20, nTelos Wireless Pavilion, Charlottesville VA
  • Other Lives — 6/2, The Southern, Charlottesville VA
  • Alabama Shakes — 6/9, nTelos Wireless Pavilion, Charlottesville VA
  • Sonny Landreth — 6/18, The Southern, Charlottesville VA
  • John Butler Trio — 7/9, All Good Music Festival, Berry Hill Farm — Summit Point, WV
  • The Motet — 7/9, All Good Music Festival, Berry Hill Farm — Summit Point, WV
  • moe. — 7/9, All Good Music Festival, Berry Hill Farm — Summit Point, WV
  • Everyone Orchestra — 7/10, All Good Music Festival, Berry Hill Farm — Summit Point, WV
  • Chris Robinson Brotherhood — 7/10, All Good Music Festival, Berry Hill Farm — Summit Point, WV
  • Railroad Earth — 7/10, All Good Music Festival, Berry Hill Farm — Summit Point, WV
  • The Word — 7/10, All Good Music Festival, Berry Hill Farm — Summit Point, WV
  • Joe Russo’s Almost Dead — 7/10, All Good Music Festival, Berry Hill Farm — Summit Point, WV
  • Primus — 7/10, All Good Music Festival, Berry Hill Farm — Summit Point, WV
  • The Wood Brothers — 7/15, Waterfront Plaza, Brookfield Place, NYC
  • Foo Fighters — 7/16, Citi Field, Queens NYC
  • My Morning Jacket — 7/21, nTelos Wireless Pavilion, Charlottesville VA
  • Phish — 8/16, Merriweather Post Pavilion, Columbia MD
  • JR JR — 11/2, The Jefferson Theater, Charlottesville VA
  • Chris Forsyth & the Solar Motel Band — 11/12, Bowery Ballroom, NYC
  • Futurebirds — 11/12, Bowery Ballroom, NYC
  • Stevie Wonder — 11/17, JPJ Arena, Charlottesville VA
  • We Were Promised Jetpacks — 12/4, The Southern, Charlottesville VA
1 January 2016
Music Lists

The Gift of Great Radio

WNRN has been a mainstay in Charlottesville since 1996. I recall discovering the station on a Saturday morning back then during their Grateful Dead show - two hours of live dead. It was love at first listen.

Years later I moved to Charlottesville and listened on a regular basis. I found out that NRN plays much more than the Dead. They play about everything you can imagine from acoustic to alternative to hip hop to 80s to bluegrass - music you won’t hear on commercial radio.

And that’s the other great thing about NRN - they don’t play commercials. They are listener-supported. Twice a year they do on-air fund drives. I started donating a few years ago, but this summer I signed up for their evergreen program. I donate 5 dollars a month for as long as I want. It’s a simple way to give. It’s also a simple way to get cool things too.

NRN has a VIP program for evergreen and other regular members. Every Monday we receive an email with an opportunity to win prizes or be included in special private events. Through the VIP program since Labor Day, I’ve seen Delta Spirit play a catered private show, had lunch with The Head and The Heart, and take my family for a catered dinner at First Colony Winery with a performance for kids by a local duo, Tom and Mary. I also won tickets to see Kings of a Belmont play at The Southern. I repeat - all since Labor Day and all for 5 bucks a month.

NRN is the best radio station that I’ve ever regularly listened to. That alone deserved my donation. Now they’ve raised the bar. Their staff and volunteers have done a wonderful job with these VIP events and giveaways. I plan to increase my donation and if you listen to NRN you should become a VIP member. If you haven’t listened to NRN before now is a good time. The Grateful Dead and Phriends show kicks off at 9 this morning.

15 November 2014

Learn By Example

I’m not a conference junkie, but I make sure to hit one, maybe two, a year. Brooklyn Beta has been my choice of conferences the last two years. Fictive Kin runs the conference and does a tremendous job. It is the best conference I’ve attended.

Last year I volunteered my time for Charlottesville’s Tom Tom Founders festival by contributing to the programming (securing speakers, not writing code). Tom Tom and Brooklyn Beta are totally different events, but there is one big overarching similarity. Brooklyn Beta celebrates making/working on something that you love. That’s why many people become entrepreneurs. Tom Tom’s innovation track focuses on founders, start-ups and entrepreneurship. Two weeks ago, Tom Tom launched Founding Cville, a program that recognizes founders from our community.

Brooklyn Beta was such a good conference because:

  1. It was extremely well run. I mentioned that already, I know. Hats off to Chris and Cameron and the entire team behind it.
  2. It was not too expensive. The price was $299.
  3. It had an atmosphere of intrigue and surprise. There is very little promotion leading up to the event. The website is always very simple. You also have no idea who is speaking until they take the stage.
  4. It celebrated Brooklyn through its vendors and sponsors.
  5. We, the attendees, were always the focus. Instead of head shots and bios of the speakers, the website displayed all of the attendees’ Twitter bios. The conference provided long breaks for us to socialize and meet new people. We had two hours for lunch, an hour in the late afternoon for beer, whiskey, and rainbow sprinkles, and the first talk didn’t even start until 11 giving us plenty of time to walk around, drink some coffee, and see who was there.

I think the innovation portion of Tom Tom can take a few cues from Brooklyn Beta. Obviously celebrating local has always been in the forefront. The fall block party last month was a great example. That could spill over to the innovation track with a local food truck serving lunch and a local beer sponsor providing afternoon beverages. Give the attendees an atmosphere to engage with one another instead of making it all about the speakers and the topics.

Even though Charlottesville is a great place to visit, the fact remains that it will always be much more difficult to get here than Brooklyn or Austin or Portland. Thus it’s going to be harder to pull in people from outside our region to attend. So let’s focus on getting a few out-of-towers as the speakers to entertain and enlighten the local (and regional) design and tech community here as attendees. The best chance to put fannies in seats is by targeting local design and tech professionals In Charlottesville, Harrisonburg, Waynesboro, Richmond, Culpeper, Lynchburg, Roanoke, and DC.

Finally I think the innovation track should provide talks that are focused on stories of creating, building, and founding something that someone was driven to do. The brand name doesn’t matter. What matters is their story. Find the best stories to inspire the crowd, mix in Mudhouse coffee, The Bavarian Chef for lunch, background music courtesy of WNRN, Wild Wolf on tap, and that crowd will keep coming back to celebrate entrepreneurship in Charlottesville on Thomas Jefferson’s birthday.

21 October 2014