A common misconception of running a business is that "growth at any cost" is the only path to success. As the co-founder of a self-care company, I felt pressure to prioritize rapid scaling, whether that meant accepting lower-quality products, scouring the globe for the cheapest suppliers, or sacrificing sustainability for short-term gains. However, I was running a business meant to improve people's well-being, not just take their money for a quick fix. I knew we had to ensure that everyone the business affected — every employee, partner, supplier, and customer — was better off after doing business with us. So, I based our success on measurements of regeneration: * Improved Well-being: Rather than focus on products sold, we look for indicators of improving social cohesion and mental health. * Localized Wealth Circulation: Rather than focusing on driving down our costs, we utilize local supply chains to retain economic value within the communities where the brands we work with operate. * Net-Positive Impact: Rather than focusing solely on top-line and bottom-line revenue, we assess whether our operations restore more than they extract. As John Doerr says, you have to measure what matters. Website traffic and conversion rates don't tell the story we are writing. So, I focus on sustainability and regeneration. Working in tandem with women running sustainable businesses means I can double down on my values. I choose brands whose suppliers follow sustainable practices, pay livable wages, and source ethically, even if it means I am paying higher prices. The investment ultimately pays off because this ecosystem of regenerative practices resonates more deeply with our audience. Letting go of the extractive growth mentality was liberating. I measure success not just by revenue, but by the health of the business, the happiness of our team, and the integrity of our impact. That's the kind of growth I want to be a part of.
That I had to do everything myself for it to be done right. In the early days of Omni, I clung to every task - product, content, design, you name it. Letting go felt risky. But once I started trusting others and giving them real ownership, the business moved faster and got better. Turns out, you grow more by doing less — if you do the right less. At Omni, we hire industry experts, so me doing less ment their expertise could shine more.
The belief I had to unlearn was that income arrives automatically. Once I left salaried work, I discovered that every dollar is earned, and even the smallest win has to count. Accepting that reality pushed me to treat learning as a daily habit. I rely on artificial intelligence to speed research and outreach, and I lean on mentors plus no-cost courses whenever I spot a skill gap. Admitting I did not have every answer to unlock rapid growth. Staffing evolves quickly. Client expectations, technology, and response times change month by month. Letting go of "how things used to work" and building processes for how they work now has kept my company relevant. In short, replacing the mindset of security with one of curiosity and continuous improvement turned fear into fuel.
One mindset shift that I had to unlearn was imposter syndrome. When we are doing something new or starting to put ourselves out there in business, it feels strange because we've never done it before. And that's when the imposter syndrome kicks in. But you can teach yourself to push through and now let imposter syndrome hold you back. Because it's just a tiny voice in our heads and taking action quiets it.
I had to unlearn the sentiment of "You need extensive experience before you can start a company." In college, I shared my dream of starting a social media agency with a mentor. She laughed. Not the polite kind, but a head-thrown-back, belly laugh. She said, "You need at minimum 10 years of corporate experience before you can even think about starting a company." My internal voice shifted from "You can" to "You are too young" and "You are not ready." I filed away my business plans and took a job at someone else's agency instead. But there was this stubborn whisper—the same voice that once convinced six-year-old me that I was the sole exception to the adult scissors rule. It kept asking: "What if they're wrong?" At 22, I started my social media agency anyway. Spoiler alert: 7 years later, my company is still going strong. I learned that someone else's fears are not yours to inherit. Your age isn't a flaw to overcome. The only permission you need is your own.
The Profit First Method, from the book of the same title by author Mike Michalowicz, fundamentally revised how I related to money in my business. Since reading the book and implementing the Profit First practices I have not only changed how I think about money, but dramatically shifted how my company relates to capital. As the title suggests it simply asks you to set aside profit first and then other essentials and then dares you to run your business on the money left over... instead of calling the profit what is left at the end of the month (if any.) I recommend this to all our clients and authorpreneurs as a game-changing practice. https://profitfirstbook.com/
The biggest belief I've had to unlearn (which is difficult for most women) is I don't have to do it alone. Once I started involving others in my business, either through strategic hires or collaborations, not only did my business grow, but my thinking also expanded. When you hold on too tight to the belief that success solely depends on you, that's a mental contraction when you need to see possibilities.
One mindset I've had to shift is believing that offering a high-quality product or service is enough to attract customers. It's not. I've had to learn, and re-learn, that success comes when you combine quality with consistent visibility, intentional marketing, and genuine community connection. We recently sold our 15-year-old restaurant, Two Keys Tavern, and we continue to run our environmental company, KLM Environmental. Most recently, we launched a travel blog, Wandering Everywhere. Across all of these ventures, I've had to constantly remind myself that offering the best, whether it's food, content, or customer service, isn't enough in today's fast-paced landscape. People have to know about what you're doing. With thousands of platforms and channels available today, especially through social media, staying visible and relevant is an ever-evolving habit, and one of the most important ones to keep growing any business.
You have to get over any shame or embarrassment about putting yourself out there. In the early days of my business, I felt like I was spamming my friends and family, letting them know about my new venture. And many did unsubscribe (which can sting, especially when you're just starting out), but it also led to some of my first clients, and many of them were (delightfully) unexpected. And then those clients recommended me to others, helping me grow a sustainable business that has existed almost exclusively on referrals for over two years.
I'd like to talk about unlearning the idea that if you only micromanage, you are assured success. During the early days of Angel City Limo, I would not delegate any aspect of the business, from driver schedules to client bookings. This micromanaging delayed us and crushed the spirit of initiative among my team, leading to our operations breaking down. Acknowledging the need for a change, I leveraged a delegation attitude and put my trust in an operations manager. We started having feedback sessions within our teams weekly, where we can express and submit possible solutions. This transition led to a 36% improvement in operational efficiency and a 24% gain in bookings in six months. Most importantly, it lets the team feel trusted and work more innovatively and quickly. Unlearning micromanagement was a key part of scaling Angel City Limo. That freed me up to work on my strategic partnerships, such as cutting a deal for a corporate shuttle that ultimately would contribute 15% of our annual revenue. My suggestion: substitute micromanagement with defined roles, constant checks, and autonomy.
I had to unlearn the belief that mistakes are a sign of failure. In reality, your business won't grow without them. I co-founded a company that creates premium fashion merchandise. Early on, we made a hilarious mistake on one of our first big orders. The thing is that we don't just print on ready-made t-shirts, we sew everything from scratch with high-quality materials. Due to a mix-up in the specifications, we ended up with one company's logo on the front and another company's logo on the back. We only discovered it when we opened the boxes and were both shocked and amused. The biggest lesson? Always double-check every detail! Production is a complex process, and having a solid system in place is what helps you maintain great quality. We now make it a rule to verify every single detail before moving forward. So, while you're likely to make mistakes, don't treat them as failures. Instead, see them as valuable lessons, and it's by learning from these lessons that your business truly grows and succeeds.
Something I had to unlearn was that success is in scaling faster. Initially, I was obsessed with growth hacks and speed "move fast and break things" kind of attitude. But in education, that breaks people, not systems. I realized that real growth occurred when we slowed down to truly listento families, to students, to teachers burning out in silence behind their screens. That shift from speed to depth changed everything. We no longer chased scale, but instead, we started to build systems that could build trust at scale. Another habit I had to get out of was lone-wolf syndrome. You're a founder, you want to be the smartest guy in the room. But Legacy only scaled once I began to hire people who were smarter than me, especially those who disagreed with me. It's humbling and required. Finally, I've learned that building a business with purpose isn't about proving that you're right. It's about building something that's right even after you're gone from the room.
One of the biggest things I've had to unlearn while growing my business is that I can't do everything—and I definitely can't do everything well. I can handle a lot, but there are certain tasks I either don't enjoy or simply shouldn't be the one doing. Over time, I've learned to farm out things like marketing strategy, ads, and even some gift design. But as much as I don't love social media, I've realized that part still needs to come from me. I'm the one in the shop making the gifts, attending events, and capturing those behind-the-scenes moments. No one else can snap those photos or shoot those quick videos in real-time. It feels a bit like doing taxes—something I'd rather avoid—but promoting my business on social media is just too important these days. So, I've learned to embrace it and make it part of my routine.
One mindset I had to unlearn was that I needed to do everything myself to ensure it was done 'right.' Scaling a company takes a different set of skills where you need to transition from hands-on entrepreneur who does it all to an enterprise-builder. Like many founders, I started as a one-woman show: I cut, joined, embossed, and assembled each frame by hand in my basement and handled all of the marketing, sales, operations, and customer service myself. That scrappy mentality served me well in the early days, but as the business grew, I learned I can't sweat the small stuff and needed to put my trust in my teammates. It's hard to let go, but the ability to embrace change and not 'micro-manage the minutiae' requires building a team of capable leaders who are stronger in their respective areas than you are and can collectively take the company to new heights. I had to learn to delegate and trust others, even if their approach was different from mine. Empowering your team is essential for building a sustainable and innovative company culture. Growth happens when you take a step back, actively listen, and give people the room to take ownership.
I had to unlearn the belief that no one else could do the job as well as I could. Initially, I was responsible for conducting every inspection, answering every call, and managing every route. I thought that was just how it had to be to guarantee "quality". However, once I started delegating and trusting the team to handle things their way, the business grew faster and more smoothly. Not only were they capable, they often brought better ideas to the table. Letting go was uncomfortable at first, but it was the only way we scaled.
For the longest time, I genuinely believed that if I didn't handle everything myself, it just wouldn't get done right. Classic founder syndrome, honestly. Sure, in those early days, wearing every hat did feel necessary, like, who else was going to do it? But after a while, it hit me: trying to steer the whole ship solo just jams up the works. Micromanaging? It's like throwing a wrench straight into your gears. The real breakthrough came once I started trusting my team to actually own their roles. Letting go didn't mean checking out; it meant purposely making space for people to step up and deliver. That shift? Not only did it unlock growth for the company, but it also forced me to level up as a leader, too.
I had to unlearn the belief that "data tells the whole story." Coming from investment banking, I was obsessed with metrics and analytics dashboards for everything. Early on at Rocket Alumni Solutions, I made all decisions based on usage statistics and conversion funnels. We were missing why our donor retention was plateauing at certain schools despite good engagement numbers. The data showed people were using our touchscreen displays, but something felt off. I finally started doing in-person interviews with actual donors and school administrators instead of just analyzing their behavior. Turns out, they wanted to see emotional stories and personal connections—not just clean data presentations on our displays. When we shifted from showing "John donated $500" to featuring donor testimonials and impact stories, our repeat donations jumped 25%. The breakthrough was realizing that behind every data point is a human story. Now I spend equal time talking to users as I do reviewing analytics. Our active user community tripled once we started building based on conversations, not just conversion rates.
The biggest belief I had to unlearn was that my past mistakes made me unworthy of real business success. Coming from eleven years in and out of prison for cannabis-related convictions, I initially tried to hide my background when starting Terp Bros, thinking it would hurt our credibility. This actually held us back massively. When we finally acceptd our story and positioned ourselves authentically as a social equity business through New York's CAURD program, everything changed. Our authentic messaging about second chances resonated with customers who became loyal advocates, and we went from struggling to get noticed to becoming one of Queens' most respected dispensaries. The turning point was when we launched our educational sessions where I openly shared my journey from incarceration to business ownership. Instead of driving customers away, it built deeper trust and community connection. We saw a 40% increase in repeat customers after we stopped hiding our story and started leading with it. Now I actively hire justice-involved individuals and train them through my nonprofit construction program before bringing them into cannabis. What I thought was my biggest weakness became our strongest differentiator in a crowded market.
After leading growth at companies from pre-IPO Sumo Logic to early-stage startups, the biggest mindset I had to unlearn was **"Financial planning is just for compliance and investors."** I used to treat bookkeeping and financial operations as necessary evils—something to outsource cheaply and ignore until board meetings or tax season. At one portfolio company I advised, the founder was burning $30K monthly but had no real-time visibility into cash flow patterns or unit economics. The breakthrough came when we implemented monthly financial reviews tied directly to growth decisions. Instead of just tracking expenses, we started using cash flow data to time product launches, delay equipment purchases during tight months, and identify which marketing channels actually drove profitable growth. Revenue per customer improved 35% because we could finally see which segments were worth the investment. Now at OpStart, I see this pattern everywhere—founders who treat their finances as an afterthought miss massive opportunities. When you have clean, real-time financial data, every growth decision becomes sharper. You know exactly when to double down on what's working and cut what's not.
The biggest mindset I had to unlearn was that I had to be the smartest person in the room to succeed. As a Brown grad and former investment banker, I thought my job was to have all the answers and make every decision myself. This nearly killed my company early on. I'd spend weeks perfecting features based on my own assumptions instead of asking users what they actually wanted. When I finally started doing in-person interviews and letting customers guide our product development, we tripled our active user community and hit 80% year-over-year growth. The breakthrough came when I scrapped a feature I personally loved because market feedback was terrible. That freed up resources to build our interactive donor wall, which became our flagship product and helped us reach $3M+ ARR. Now I actively seek out people smarter than me in specific areas and let them lead. The hardest part was admitting that my expertise in finance didn't automatically translate to product development or customer needs. Once I acceptd being the dumbest person in rooms full of educators, designers, and users, everything clicked.