Aug 19, 2015 - Things to Do

Fast advice: 11 things I learned by quitting my job (most are personal)



My wife, Lindsey, and I both quit our corporate jobs at the same time (about 150 days ago). Our son, Watt, was 4 months old.

Here’s the interesting thing, we both loved our jobs.

Lindsey planned events at Bank of America and I was the Director of Digital Strategy and New Initiatives at the Charlotte Observer. We were both happy and loved our coworkers.

But, we decided to quit.

Lindsey wanted the opportunity to spend more time with Watt. I had this overwhelming fear that tomorrow’s media companies are being born today and I would be caught on the sidelines watching others build them.

Let’s be honest, it’s horrifyingly scary. I’m scared every day.

It’s so much easier to enjoy your job and click refresh on your Bank of America checking account every other week on payday. Yes, some days I want to curl up in a ball and cry because I miss that so much.

I want to share a few things I’ve learned with the Charlotte startup community with the goal of demystifying quitting.

(1) Health insurance. It’s intimidating, but it’s really not that hard. Lindsey and I sat on our living room sofa and went to We studied the available plans and researched which plans covered our current doctors. We ended up choosing a plan that costs about $700/month and we were able to keep all of our current doctors. If you’re young and single, plans are relatively inexpensive.

(2) The law. If you’re starting a business, get the legal stuff done right. It’s worth it. I feel so fortunate to have hired Justin Agans. His transparency and turnaround times are insane. The work he did for me included: LLC docs, freelance writing agreements, privacy policy, employment agreement review, user agreement and advertising contracts. My total bill was much less than I budgeted (don’t tell him). Hire him, seriously. Having this done right also took away the fear that I would have a shaky foundation for what could be a serious company. Now, the foundation is solid.

(3) Place to work. Some people (ex, Katie Levans) can just work via laptop at places like Earl’s Grocery or 7th Street Market. I’m not one of those people. I highly recommend a coworking space – Industry, C3 Labs, @809, Level Office (coming soon), Advent Coworking (coming soon), Hygge (coming soon). These spots will have different membership levels (desk, dedicated desk, office) and prices typically range from $50 – $750 for monthly memberships. I work out of @809 and I love it here.

(4) Connect with other founders or former founders. Non-founders don’t understand what it’s like to start something. They read Good to Great and think their management principles work at startups. I’ve found it very helpful to be able to pick up the phone and talk candidly with people like Mark Bruinooge and Chris Halligan (both have lived it before). They understand the emotional side of starting a business. Seek out other founders – they’re the only people with the right type of empathy. But, real founders don’t have time for wannabe entrepreneurs – if you haven’t brought something to market or if it’s just part time, nobody cares.

(5) Find a partner. I’m a psycho. It’s hard for me to trust others when it comes to shaping the Agenda. By far, the best decision I’ve made as a business owner was partnering with Katie Levans. We are extremely different people, but similar on the stuff that matters: integrity and effort. Partnering with Katie changed the Agenda’s trajectory, but – it wasn’t easy. Just ask her about the countless times I gchatted her asking, “Are you sure you know how to send the newsletter? This is how we do it.” Katie finally freaked out on me and said, “Ted, I know how to send a damn newsletter.” The first day she sent it, we set a record on open rate and visits to the site. Find a partner who you respect and has more talent than you… then trust them.

(6) Personal cash burn rate. Lindsey (my wife) and I sat down and mapped out all of our personal fixed and variable costs on a Google Speadsheet. We know our exact monthly cash burn rate and we compared this with our savings. We know the exact runway we’re comfortable with. Knowing this burn rate allowed us to plan for the long term and to set financial goals for our family. It was critical for our peace of mind to know what we’re risking.

(7) Startups are more than just tech startups. Our city has some incredible entrepreneurs – 99% of which aren’t in tech. A founder is a founder is a founder. Look outside of tech for a mentor and advice.

(8) Early revenue partner(s). I didn’t want to raise capital, so it was important to me to have a partner from day one. But, not just any partner. I needed a partner that would trust us, provide feedback and grow with us. I’ve always been 100% transparent with OrthoCarolina and they’ve been an outstanding partner as we figured out ad products together. I love them. Instead of bringing on a bunch of partners, I decided to bring on the right partner. It was a small decision, that changed everything. I love OrthoCarolina, but I hope I never have to use them :).

(9) Ask for help. This is hard for me. I’m used to knowing the answers and having other people ask me for help. It’s hard for me to go to Garrett Tichy and ask him to help me optimize my WordPress site because I don’t know what to do. It’s hard for me to go to Dave Oakley and ask him to help me evaluate ad products because I need help. It’s hard for me to ask Tim Cheadle what type of font we should use because I don’t know fonts. It’s hard for me to ask Kate Civali (who used to work for me at the Observer) how to setup ad serving technology. For whatever reasons, Charlotteans are very giving with their time. Stalk somebody on LinkedIn and ask them for help. Be specific on what you want them to do; smart people are busy.

(10) Listen. I’ve found asking the question, “If you had one piece of advice for our media company, what would it be?” to be very, very helpful. Go get feedback. Pitch your startup at pitch breakfast. Go ask investors for money. Don’t be afraid of sharing your idea and becoming vulnerable. But even more important, make sure to actually listen.

(11) Massive failure isn’t that bad. More Charlotte employers and hiring managers are valuing entrepreneurial experience. In my opinion, this may be one of the most important things for our city’s entrepreneurial growth. This means that even if you stink and fail, those skills and battle scars will make you stand out for your next job. It’s no longer a resume killer. Think about it; If you’re a company or hiring manager looking for breakthrough innovation (who isn’t), would you rather hire the perfect resume or the person that has brought an idea to reality?

Quitting isn’t for everybody and I don’t recommend it unless you’re psycho. Hope this helps.


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