“We're going to get through this. It's okay. And… It's not going to be fun. But then that quote comes back, ‘This too shall pass.’ It's going to pass like a kidney stone, but it's going to pass.”

As founders, our paths to entrepreneurship don’t always look the same.

Some have heartfelt dreams that are years in the making. Others might notice a gap in an industry and decide they'll be the one to fill it.

And sometimes, our identity might end up on the dark web, and after the horrible, life-changing experience, we decide: no one else should ever have to deal with what I just went through, and I’m going to be sure of it.

That’s exactly what happened to Amy Wood, leading to a new mission in life and the founding of Copper Penny Consulting.

The mishap that changed her life and her career

“When this all happened, I was like, this is ridiculous. Our dental offices are at huge risk and a lot of it falls under HIPAA… So that's when I decided to just fully embrace this new direction.”

For most of her entire adult life, Amy had been self-employed. Working as a fractional IT provider alongside her husband, Scott, for nearly 20 years, the idea of “being your own boss” was deeply engrained.

They catered their services to small practices, especially dental, that just didn’t have the budget to have their own IT person on staff.

Ironically, a 2013 data breach at the dental office where she was a patient led to big changes she never planned on making.

“I found out my dental x-rays had ended up for sale on the dark web, along with my name, birthdate, social security number, and my insurance medical record number. I started having identity theft. I started having fraud, impersonation… I had all kinds of things. And it still comes up.”

At that point, the work Amy had been doing with IT and cybersecurity was all intertwined with the very things that had failed her with this breach.

It only made sense to take matters into her own hands.

She and Scott started a second business that would tackle IT and HIPAA together, eventually building a team and becoming a one-stop-shop for any needs a dental office may have.

“We started adding OSHA, infection control, human trafficking, and opioid prescribing safety for dental professionals. Basically, we're turning into all things safety, compliance, and regulation.
There aren't many companies that actually have experts that will do all those things. And on my team, we have people that are experts in their own rights.”

Right before COVID hit, they were unhappy continuing the IT work they had been doing for 20 years. They sold their business, moved back to Amy’s hometown, and decided to go all in on Copper Penny Consulting.

The unexpected fear that came with growth

One of the hardest parts of becoming a founder is the fact that we make our own rules. There’s no playbook to lead us step by step through what we “should” be doing.

But for Amy, who had been self-employed for so long, fear didn’t show up when it was time to dive into the new business.

“I was like, I understand all the pros and cons. I know that if it's really good, I'll benefit, and if it's really bad, I might not take a paycheck, or I might have to contribute extra money… So, I kind of went in knowing all of that. But it doesn't make it any easier.”

At that point, any uncertainties were overshadowed by the fact that there was a serious problem she knew she could solve.

She started gaining work in her new consulting business by reaching out to existing clients. Slowly, it began to grow and she was faced with a new challenge she never expected: She was being asked to speak at events.

“I was aggressively getting booked on stages, so then I spent a lot of time on my end learning how to be a better speaker, be a better presenter, have better slides, learn how to do activities. That's the part where I definitely had Imposter Syndrome.”

It’s interesting how Imposter Syndrome can sneak in when we’re tasked with doing something new, even when it’s related to something we’re entirely skilled at or qualified to do.

“I knew what I was doing. I worked directly with Health and Human Services and the Office for Civil Rights. I've done over 500 data breaches, I've worked with all these HIPAA-specific attorneys and forensic people, and I'm on a task force with the FBI…
I'm involved in all these government things, and that part doesn't scare me anymore. But getting up on stage, especially in front of my peers and not saying ‘um’ 47 times, was daunting.”

The speaking engagements only grew. More frequent opportunities, bigger stages… But by taking her fear into her own hands, she was able to build her confidence on stage.

All while making boring topics like HIPAA fun.

This makes the struggle worth it

“I mean, I would like a paycheck at some point. I have that safety net, but it would be really nice to start contributing again, and not feel guilt. Thankfully, it's starting to turn around.”

Moments of struggle still like to creep in, even as Amy continues to nail her stage presence and experience major successes with her clients.

It’s these wins, no matter how big or small, that make it easier to keep her eye on the future goals.

“Whenever I speak with a client or a meeting attendee, anyone that says, ‘I didn't know that,’ or ‘I didn't know it was that easy to fix…’ those are the moments where I know I made an impact. Something that I said helped them make their lives easier, or more secure for the patients.”

Having directly dealt with the very problem she’s working to eliminate, Amy holds a certain level of empathy and passion when it comes to working with her clients.

She truly never wants her clients’ patients to be in the same position she’s been in.

“When someone has a data breach, I tell them, ‘Hey, this isn't going to be the end of the world. We're going to get through this. I know exactly what I'm doing, I'm not new at this.”

And her approach works. To date, she hasn’t had fines, penalties, patient lawsuits, or bankruptcy in any of the data breaches she’s worked on.

So in those moments that feel particularly rough, every success is a reminder she’s making a difference in people’s lives.

And her team is always there to make sure she never forgets that.

You’re never alone when you build a strong team

Amy will be the first to admit, her incredible team is what makes Copper Penny Consulting so successful.

“I'm very fortunate that I have a team of ladies that are just… They're all in. They go above and beyond. I am beholden to them. I know that they've got my back, and they're not going anywhere.”

Part of what makes her team so powerful is how she approaches leadership.

Amy sees people’s potential and invests in them, aiming to be less of a boss and more of a mentor, or a guide.

“When I took on my OSHA and infection control person, Deanna, I was more than a mentor. I was like, I want to mentor you, yes… But I also want to teach you how to do these things, and I'm going to throw you in the deep end, and make you do hard things, and break you down, and build you back up.
But now she's gotten on stage with me, and she just crushes it.’”

This investment she makes in her team never fails to pay off, often leading to deep connection and mutual feelings of respect.

“Deanna had talked about the struggles of her previous employment, and how I took her under my wing and gave her freedom and flexibility, but gave her some structure to follow, and lots of encouragement. And, so that hits hard.”

Those on her team are invited, and encouraged, to have an active voice within the business. They lean into their strengths and aren’t afraid to reach out to others when they need help.

“I feel like I'm steering the ship and giving some of the ideas, but at the same time, they're all invited to come with their ideas and create things of their own to make them happy and more efficient as well.”

Key takeaways from a lifetime of self-employment

With a little bit of seriousness and a whole lot of fun, Amy’s pretty clear on what she’s learned through this journey so far.

🌱 Kindness, patience, and empathy goes a long way

It doesn’t take much to be kind. And remember, your face has subtitles. If you’re thinking something unkind, your face may be showing it.

🌱 Don’t be afraid to have fun

“I talk about boring topics that are scary and daunting and overwhelming and grossly misunderstood, especially when we talk about cybersecurity and technology… I have to have fun with it.”

🌱 Get creative with how you approach communication

“I took an improv comedy class during COVID, and I have to say that is the single best thing that I've ever done for me as a consultant, to actually communicate with people on the fly, and try to have fun with them.”

🌱 Make time for hobbies that bring you joy

“I think once you turn 40, you have to have an old lady habit. Mine turned into gardening and home restoration."

Living in a 1876 Victorian home, she’s always on the hunt for unique antiques and old restored items. It’s turned into a hobby that also adds life and character to her house.

When’s the last time you audited your own wellness?

You get plenty of advice. What you rarely get is a pause. Each month, we’ll share a simple prompt to help you step out of execution mode and consider what “founding well” looks like in your world right now.

Reflecting on your past self can help you reconnect with the spark that got you started, before growth targets and investor updates became the daily measure.

It’s less about “Am I succeeding?” and more about “Am I honoring the person who started this journey?”

Feel free to pull out old fashioned pen and paper, or create a new doc just for journaling, and spend a few focused moments thinking about the following:

What would the “me” who first had this idea think of where I am today?
What would they be proud of, surprised by, or disappointed to see?
How did I imagine this would feel when I started?
What promises did I make to myself early on? Have I kept them?
How would that earlier version of me feel about the trade-offs I’ve made along the way?

There’s no right or wrong answer. If nothing comes up, that’s okay too! Use this as space to notice what is real for you today. A few messy lines are enough.

If you're comfortable sharing your insights with us, we'd love to hear them! Let us know at foundingwell@vallelegal.com.

The good that came from a data breach 🦷