The biggest leadership lesson has been learning to compete strategically against companies with larger advertising budgets. By focusing on building genuine relationships through business communities and creating a multi-channel content strategy that prioritizes earned media over paid advertising, we've been able to punch above our weight. This approach proved that authentic engagement and authoritative content on platforms like LinkedIn can level the playing field when you can't outspend the competition.
The biggest leadership lesson from this year includes transforming how I develop teams. As an entrepreneur, mentor and parent I was disjointed, cluttered and constantly scattering. I had leadership styles for each form of work, and some worked, some didn't and some were sporadic with results. It wasn't until I took a step back and started to realize that I could apply one type of leadership style to my entire life. As such, I created a series of daily non-negotiables that applied to running multiple side hustles, helping aspiring entrepreneurs start their own side hustle, and parenting. Instead of becoming the boss, I wanted to take a different approach. First, I focused on outworking everyone around me. That included more reps, more calls, more published content, more meetings, more everything. I didn't work longer, I just jam packed more into the hours I did work. Second, extreme coachability. I wanted this to be a two-way street whereas I learn as much from my clients, collaborators, and kids as much as possible. Third, maximum positivity and uplifting. Every day, I try to spread as much positivity as possible with each interaction and uplifting others through continued support, asking the question, "How can I help you achieve your goals?" or "What can I do for you today that will help you get a small win?" It's been tremendous for PR, it's been contagious, and has been mentioned numerous times that other entrepreneurs and organizations are adopting this approach.
2021 has taught us that true leadership is about taking action before you are forced to, and this was demonstrated by the decision that we made to invest in automation a long time before this current wave of customer claims began to disrupt the market. The risk for us was to divert budgets from short term income, and focus on building out our onboarding and claims processing infrastructure from scratch, however it allowed us to then scale without affecting accuracy, quality and trust. The most significant outcome has been in enabling the team to question existing processes, and innovate solutions that not only reduced our turnaround times significantly, but also increased transparency for customers who have been let down by other financial institutions in the past. One lesson that I have taken from all of this is that leadership isn't about being the most vocal person in the room, but rather about providing direction, having faith in your team to take action, and remaining responsible at all times.
This year we changed everything by adding more daytime, evening, and weekend therapy spots. We went back and forth on it, but it was the right call for families who are constantly juggling schedules. We're finally seeing people who could never make it in before. Honestly, my advice is just meet people where they are, even if it means scrapping how you've always done things.
I thought scaling Medix Dental IT to over 1,000 dental practices meant losing our personal touch. I was wrong. We built small client advisory teams who actually knew the practice owners by name and understood their specific IT headaches. That direct connection is what kept them with us. Turns out you can get bigger and still stay close.
At Magic Hour this year, our sports video edits hit 200 million views completely by accident. The reason? We weren't chasing some algorithm or shortcut. We just focused on real emotion and teamwork. It showed me that what actually lasts in media is connecting with people, not using the latest tech trick. If you're trying to grow, focus on real stories. That's what works.
This year I bet big on automation at CLDY.com. We had to retrain the entire team and basically rewrite how we did everything. Getting everyone up to speed was a tough few months. But now we get back to customers way faster and can handle bigger projects without running our team into the ground. If you're scaling, my advice is to do it early. The upfront headache is worth it.
Taking Dirty Dough from an idea to 100 stores in two years was something else. We made it work by letting the numbers pick our new markets and keeping our operations tight. It wasn't always smooth; we had to switch up our real estate strategy a few times, but trusting the data kept us on course. The big lesson? Be ready to change direction fast when the numbers tell you to.
This year I realized we only win when our clients win. We switched our pricing to focus on actual results, and suddenly my team stopped caring about task lists and started figuring out how to actually move the needle for clients. In a crowded marketing world, this made us different and clients stuck around longer. My advice is to tie your success directly to your client's results. It's hard, but it works.
This year I took RentalRealEstate from a simple blog into a site homeowners actually use. Instead of just hoping for clicks, we built the platform around the real questions people were asking, and our numbers climbed steadily. After adding webinars and some calculators, the same people kept coming back. What I learned is that listening to what people want and responding quickly is what makes an online business grow.
When we were scaling YEAH! Local, I learned remote leadership isn't about task lists. It's about the five-minute call to ask how their weekend was. My marketing background showed me that clear feedback works, and I saw that when people knew they weren't going to be blindsided, they just took the initiative. The work started moving faster. So, spend more time telling someone they're on the right track than you do correcting their mistakes.
This year I learned that trusting my team is what actually grows the business. We were always struggling to keep good people, so we started cross-training everyone and sharing our actual goals. Suddenly, my staff started solving problems on their own, and customers noticed the difference in service. If you work in a tough industry like hospitality, just listen to your people and trust them. It works better than any strategy.
At Lakeshore Home Buyer I realized hiring wasn't about resumes. We just started being completely open with the team, sharing the wins and the bad screwups. People started working harder. They started caring about the outcomes like it was their own company. That honesty is what let us actually grow. It's the only thing that worked.
The big thing I learned this year? Don't put all your money in one type of property. We had some single-family homes, and when that market got unpredictable, our few duplexes carried us. Having that mix was everything. If you're getting into real estate, I'd say don't wait to diversify. It saved us when one sector slowed down completely.
The biggest risk I took was closing properties in just seven days. It helped people in tough situations and got our name around town locally. That quick service built trust faster than any sales tactic. My advice? Earning trust is the best way to compete, especially when you're up against an industry that's been doing things the same way forever.
Getting our AI scheduling tool for Tutorbase off the ground was tough at first. But now, a few months in, hundreds of language centers have cut their admin work in half. Teachers suddenly have more time for students instead of paperwork. Seeing them focus on actual teaching, that's the win that matters most to us.
When the market got volatile we didn't panic. For our bridge loans, we kept rates the same but got much stricter on who we lent to. I mean we called every single reference ourselves. It took more time, but we didn't lose a single loan and our clients were relieved. The lesson I learned is that when things get crazy, going slow is actually going fast.
At ShipTheDeal, we stopped relying on paid ads and focused on getting found through search. That shift let us scale faster while spending less, which was crucial when our budget got tight. It's a better long-term bet than short-term campaigns and helped us reach customers in new places. If you're just starting out, I'd make search a top priority.
When demand for our teen mental health services exploded, growth felt impossible. But once we stopped focusing just on the numbers and started actually supporting our team, everything shifted. We invested in training, we listened to their feedback, and they came through with new ways to get the work done. I learned that when the pressure is on, your best move is backing your people.
I was nervous about hiring younger people at Jacksonville Maids. I thought they wouldn't stick around. But I gave them flexible schedules and actual control over their work, and it changed everything. Our service improved and our team is way more loyal now. Honestly, giving new people a real chance has been huge for us.