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Lessons Learned: Local Business Owners Share Their Early Career Mistakes

September 24, 2017 by Michelle Boudin

Charlotte is a great place to live and, in recent years, a great place to build a business. That’s not just Chamber of Commerce talk, there’s a national magazine or big-time survey proclaiming it just about every month. But even then, it can be tough to build a business from scratch, and there are often bumps along the way. Those bumps can lead to bruises — or bigger things. So we asked some of Charlotte’s most successful business leaders what mistakes they made, and what they learned in the process.

Mistakes Made, Lessons Learned

Betsy Hauser Idilbi, Founder and CEO, Tech Talent South

Mistake: Not bringing in outsiders early on

Takeaway: The addition of investors – for their cash and know-how – can bring the company to the next level.

“I think the mistake that impacted me the most was putting too much pride into ‘bootstrapping’ the company. While it’s fantastic to build a profitable company and hold out on bringing in outside capital until it makes sense, I wish I had recognized the ‘make sense’ point a year or so earlier in our journey. Despite continued profitability, it became smart to look for investors when the company essentially outgrew the hustle and heart of our young team. We had amazing folks stepping up to work on projects that were outside their pay grade and significantly outside their comfort zone. The addition of capital allowed TTS to acknowledge that we, as a company, needed the wisdom of folks with experience to take the company to the next level. Adding the right people in leadership also provided me, as the founder, the ability to re-focus on mission and strategy for the future of the business. That change has re-energized my work and created a better culture for longtime employees as well.”

Betsy hauser Idilbi, Founder and CEO Tech Talent South  

Betsy Hauser Idilbi, Founder and CEO, Tech Talent South

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Angel Rutledge, COO and CMO, SignUpGenius

Mistake: Viewing challenges as potential failures

Takeaway: Tackling challenges leads to growth

“There’s nothing better for developing humility than running a growing technology company with your spouse while raising four teenagers. I have to fess up to not knowing exactly what I’m doing on an almost daily basis. That used to bother me a lot because I didn’t want to be the reason anything failed. Then, I started to realize that the most challenging areas were the ones where I could look back and see the most growth over time, and the biggest setbacks often led to the best new opportunities. Running a business is much more like climbing a mountain than running a 5k. I have a card my husband gave me on my whiteboard that says, ‘The best view comes after the hardest climb.’ It’s a great, consistent reminder to me to embrace the challenges as they come, and keep climbing.”

Angel Rutledge, COO and CMO, SignUpGenius

Dianne Espositio, Owner and Co-Founder, Split Second Sound

Mistake: Trusting employees to do what owners should have been doing

Takeaway: Read the dotted line!

“You think you have it all figured out, and you begin to let down your guard thinking you hired a replica of yourself. You begin to trust and not oversee important things. We had a manager and thought she had the ingredients to run our operation. We fell short in managing our manager, overlooking incredibly important documents. She wrote out a contract for one of our DJs and a couple of words flipped the contract around so that one year later we found ourselves in a legal battle. Our hard lesson is that if you have contracts or anything that can be legally binding, you as owners must take the final look at it. Never trust anyone to write them unless it is your lawyer or financial advisor.”

Dianne Espositio, Owner, Co-Founder

Dianne Espositio, Owner and Co-Founder, Split Second Sound

Ivy Robinson, President, Ivy Robinson Events

Mistake: All work and no play isn’t fun for anyone.

Takeaway: The importance of separating business and personal life

“One of the mistakes I made (trust me, there have been more than one!) in 16 years of business is not having boundaries between my business and personal life. I let my business life dictate my personal life. In the event industry, we work a lot of nights and weekends. This lifestyle had me either missing or always working on family trips, birthdays, friends’ weddings … and I would be available to my clients 24-7 because I wanted to provide the utmost customer service. But with that approach also came no boundaries, and I was enabling my clients to feel like they had the liberty to reach out anytime and I started realizing that an 11 p.m. panic call could probably wait until the next morning when I wasn’t with family or friends. So I learned to say no, not answer and put my life and myself first again. My business was in control of me, and it was time to take over and get back in control of my personal life. So far, I think it’s working.”

Ivy Robinson

Ivy Robinson, President, Ivy Robinson Events

Ross Saldarini, President, Mountain Khakis

Mistake: Not being patient

Takeaway: Take the time to get it right the first time.

“Incredibly, my partners and I failed to wash-test our sample fabric on our initial launch product. It’s a very routine step any apparel maker takes in the development of a new style, so there is no excuse. We blew it. We shipped to our first three dealers who had taken a chance on us, and everyone who’d bought the new pairs had a problem. They fit great, the fabric was amazing and the product looked great. Until you washed and dried it. Coming out of the drier, a beautiful pair of Mountain Khakis turned into a big heavy ball of canvas. The wrinkles took hard work to get rid of! We delivered new and improved product with the following shipment and learned a valuable lesson – temper the enthusiasm a bit in the early stages, the customer wants your great new product, but they want it even more if it performs correctly. Patience is a difficult virtue to maintain in startups. By applying just a bit, you might avoid a near-death experience for the company.”

Ross Saldarini, President, Mountain Khakis

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Chris Harker, Owner, Triple C Brewing Company

Mistake: Going into business with friends

Takeaway: Sometimes you have to keep friendship and business separate.

“I found out the hard way that going into business with friends can be tough and that a signed operating agreement with an agreed to exit strategy was a very good idea! We just opened a new event space and celebrated our 5th anniversary … so it all worked out in the end.”

Chris Harker, Owner, Triple C Brewing Company

Haley Bohon, Founder, SkillPop

Mistake: Doing something because it’s what you’re ‘supposed’ to do

Takeaway: Don’t follow the rules that aren’t there.

“Even though I knew it wasn’t the right fit, I felt guilty leaving my first job out of college because I hadn’t been there very long. I knew in my gut that it wasn’t the career path for me, but a tiny whisper of ‘three years, minimum!’ in the back of my head made me feel like I was making the wrong decision. I took a deep breath and took the leap anyway, leaving my stable corporate job for an up-and-coming tech startup. Looking back, staying on for additional experience at the wrong job would have been just that – experience at the wrong job. Now that I’ve launched a growing startup myself, I’m grateful that I made the move and even more grateful for what I learned – to not follow the rules that aren’t there.”

Haley Bohon, Founder, SkillPop

Haley Bohon, Founder, SkillPop

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