Powerful Lessons from the Unconventional Experiences of Seasoned Entrepreneurs

Posted September 27, 2016 by office

Life’s most valuable lessons are learned not from immediate success, but rather from picking yourself back up after failing. In the ego-fueled world we live in today, we often hear of the triumphs and shining moments of successful entrepreneurs. It’s not every day that you can hear candid advice from leading entrepreneurs and founders about what they would have done differently on their path to success.

That’s where Hindsight 20/20 – MakeOffices’ new monthly speaker series – comes in. Hindsight 20/20 highlights the experiences of successful founders—from the daunting challenges, to lessons learned in hopes of inspiring budding entrepreneurs and creators. Our inaugural event featured Tim McLaughlin, Founder and Chairman of Siteworx, an agency crafting digital solutions for B2B companies, and partner at Vienna, VA-based Caboose Brewery. Tim is a serial entrepreneur, having started five other companies, and also helps numerous founders start and grow their businesses. At the event, Tim shared stories of his unconventional entry into the tech scene with our community of “visionaries” and offered up valuable advice. In case you missed it, here’s a recap of Tim’s insightful talk:

Forge your own path, even if it’s unconventional

When Tim moved to the DC area in 1999 during what he calls “an interesting and different time period,” being an entrepreneur was not something that was universally accepted. At the ripe age of 26 after a brief stint at Lockheed Martin, Tim co-founded Siteworx, then a ASP (applications service provider) company, as chief technology officer. The unconventional route of leaving the security of a global giant to co-found a startup may have been risky at the time, but ended up launching Tim’s career into the right direction.

Sometimes you have to “fake it till you make it”

When the vision at Siteworx pivoted within three years of him joining the company, Tim also had to pivot—from CTO to CEO. Although Tim was the youngest in the company by 10 years, and as he describes, “probably not qualified,” he took the responsibility in stride. That’s not to say there weren’t difficulties along the way.

You’ll have to do things that aren’t necessarily “fun”

Being successful may seem glamorous with rose-colored glasses, but it’s not always going to be that way. As CEO of Siteworx, Tim said he learned that he sometimes had to do things he didn’t want to do if it was in the best interest of his company. Around 2009, Tim decided to focus fully on Siteworx, meaning he had to shut down a couple of companies he was growing because they were becoming distracting. Tim reflects that making that decision took a lot of willpower “as a techie nerd who always wants to be doing new things, not just growing sales and working in management.” Tim’s advice is to find something you love, but realize that there will be times when you have an obligation to the business to take on responsibilities or make decisions that are not always “fun.”

Follow your passions, but be smart about it

A self-described “beer geek and foodie,” Tim and a friend initially started Caboose Brewery, a Vienna-based brewery and restaurant, as a hobby. While Caboose Brewery began as a passion project, Tim also knew it had real potential to be successful. “We ran the numbers and realized that this was a real business here.” Tim remembers, “I wanted to start something that was both scratching an itch that I had as well as addressing a market.”

While one of Tim’s tech companies shut down, Caboose started to make real strides, and is now a mainstay in the Vienna restaurant and craft beer scene. Caboose is also poised to open a 6,000-square-foot facility in the Mosaic District in Fairfax, VA in early 2017.

Don’t waste time over-analyzing

One of the problems entrepreneurs run into is getting caught up in over-analyzing, and not actually going out there and doing it. Tim’s advice for budding founders? “Do it, see if it’s wrong, then adjust.” Although there are many things Tim wished he would have done differently in hindsight, one thing that he has no regrets about his inclination to take action.

Business solutions are not one-size-fits-all

Find what works for your company, even if that doesn’t align with other business’ definition of success. For Siteworx, that meant taking on clients who were not as well known, or as Tim calls, “sexy,” as popular consumer brands like Coca Cola. He found that these underserved companies – some of them billion dollar businesses – were the sweet spot for his business and provided much higher returns than seeking universally well-known brands.

Expect (and embrace) the unexpected

A theme throughout Tim’s experience is that while there were things he would do differently in hindsight, the unexpected twists and turns ended up helping him get to where he is today. Tim reflects that after spending his days coding and his spare time practicing classical guitar, his wrists were fatigued to the point where he struggled doing everyday tasks like turning a doorknob. What seemed like a death sentence for a techie ended up instigating his transition to management—something Tim has a natural knack for. Navigating the uncertainties of starting and growing a business is nothing short of a monumental challenge, but knowing that other founders face similar challenges can be a source of inspiration.

Hindsight 20/20 will continue to shine a light on successful entrepreneurs and creators in hopes of sharing insights, advice, and lessons learned with aspiring founders. Next month, we’ll hear from Shy Pahlevani, Founder of LiveSafe, a mobile safety communications platform, and Co-Founder of HUNGRY, a fresh-cooked meal delivery service. Join the Hindsight 20/20 meetup page to stay in the loop about our exciting speakers each month!