One of my earliest mistakes was believing that following the "safe" path would eventually feel fulfilling. I was studying dietetics, memorizing how to manage disease, but deep down I knew my heart was elsewhere. I stayed longer than I should have—afraid of failure and afraid of letting people down. The boldest move I ever made was dropping out. It felt like stepping off a cliff. People questioned me: How will you ever succeed in your business without a degree? But my gut said otherwise. I chose purpose over permission, and that decision led me to massage therapy, yoga, and ultimately co-founding Blooming Botanicals. Here's the surprising truth: there is no safe path. Security is an illusion. What's real is the fire inside you. Skills can be learned, but desire is what carries you through the messy middle. If something keeps tugging at you, listen—because the scariest leaps often land on the ground you were meant to build. Sarah Birney Co-Founder of Blooming Botanicals https://bloomingbotanicalshemp.com/
Maurina Venturelli, Head of Go-to-Market, OpStart, opstart.co My costliest mistake early on was not viewing financial operations as a strategic growth lever, but rather a necessary compliance burden. This led to delayed insights into critical metrics like burn rate, making investor conversations unnecessarily stressful and hindering proactive decision-making. I now know that clean, accrual-basis financials are foundational. The boldest move that absolutely paid off was at Sumo Logic, where we aggressively invested in marketing-led programs to drive demand. This conviction wasn't always mainstream, but our programs ultimately generated 20% of total ARR and were crucial in taking the company public. It proved marketing's direct impact on the bottom line. A surprising piece of advice that contradicts conventional wisdom: don't chase ARR at all costs. My experience, including as a VC associate, taught me that not all ARR is created equal. Focus on the *quality* and *stickiness* of your revenue; investors increasingly prioritize sustainable, repeatable income over inflated numbers.
**Nina Golban, Founder, SunValue, sunvalue.com** My costliest mistake was rushing a nationwide content rollout without proper localization research. We published solar installation guides that ignored state-by-state regulatory differences, nearly tanking our SEO rankings and credibility. Now I always pause for regional validation--those two extra weeks of research saved us from an 18% bounce rate spike and potential authority penalties. Our boldest move was pivoting to a "journalist-first" content model when AI-generated spam flooded our keyword space in early 2024. Instead of competing on volume, we invested heavily in expert interviews and local case studies. This defensive strategy actually grew our referring domains by 27% in six months while competitors lost ground. Here's what contradicts conventional wisdom: emotional messaging consistently outperforms logical benefits in solar marketing. "Protect your home from rising energy prices" crushed "Install solar to save money" by 32% in our A/B tests. People buy solar with their hearts first, then justify with math--not the other way around. The lesson that changed everything was treating content failures as market intelligence, not just losses. When Google's algorithm updates hit our AI-generated articles, we used traffic drops as signals to double down on human expertise and real-world examples.
Edgar Kleydman, Co-Founder, Kaya Bliss Dispensary, kayablissnyc.com One costly misstep was profoundly underestimating external regulatory and construction timelines. The Department of Buildings delayed our store's construction, forcing a rapid pivot from physical opening plans to virtual education and social media engagement. Looking back, I'd build in much more significant buffer time and pre-plan agile marketing strategies for unexpected bureaucratic problems. The boldest move that truly paid off was openly leveraging my personal journey, including overcoming challenges within the justice system, in our brand story. This authenticity resonated deeply, attracting local influencers and collaborators who shared our values. It truly helped foster a strong network and community even before our grand opening. A surprising piece of advice that contradicted conventional wisdom is that vulnerability can be your strongest asset in business. Instead of downplaying personal narratives or a strong social equity stance, embracing them openly fostered profound trust and loyalty. This transparency attracted both a dedicated customer base and top talent who believed in our mission, showing shared values are paramount.
**Sean Swain, Founder, Detroit Furnished Rentals** My costliest mistake was using personal savings to fund everything instead of securing proper business credit early on. Despite having good personal credit, I waited too long to establish business lines of credit, which limited our growth when we needed to scale from one property to seven units quickly. Now I tell every new host: separate your finances from day one and build business credit immediately, even if you're bootstrapping. The boldest move was switching from generic Airbnb listings to targeting traveling nurses and corporate professionals specifically. I redesigned our units with dedicated workspaces, partnered directly with local hospitals and corporate offices, and offered extended-stay discounts. Our occupancy rate jumped to nearly 100% because we solved a specific problem instead of competing with every other "cozy downtown loft." Here's my unconventional wisdom: Don't chase the highest nightly rates. When we started offering last-minute discounts for bookings within 24-48 hours, other hosts thought we were crazy. But filling those empty nights at 70% of our rate beats 0% occupancy, and many of those "discount" guests became repeat customers who now book at full price.
**Charles Kickham, Managing Director, Cayenne Consulting** My costliest mistake was letting a client launch their fundraising campaign with a valuation in their business plan. I learned this lesson watching investor after investor immediately reject otherwise solid plans because the price was either too high or suspiciously low. Now I coach every entrepreneur to never include valuations--your job is to tell a compelling story that gets you to the negotiation table, not to price yourself out before the conversation starts. My boldest move was turning away a $50K project because the client refused outside review of their plan. They'd been "perfecting" it internally for eight months and insisted it was ready. Six months later, they came back after zero investor interest--we rebuilt it from scratch and they successfully raised $2M. Sometimes saying no protects both parties. Here's my contrarian take: Stop obsessing over your business plan's perfection. I've seen entrepreneurs spend 18 months tweaking financial models while competitors capture their market. The "500-hour rule" I share with clients isn't about creating a flawless document--it's about getting investor-ready fast enough to actually matter. A good plan executed quickly beats a perfect plan that's six months too late.
As Dr. Barbara Eaton, a business coach with decades of entrepreneurial experience, I've steerd the highs and lows of building and scaling. My journey, from launching my first practice to leading a seven-figure enterprise, has been rich with lessons. My costly mistake was prioritizing relentless outward growth over my well-being and family. My children were "paying the price," wanting presence not prestige. I'd now build a business that rises *with* me, not rests *on* me, integrating peace and purpose from day one for sustainable growth. The boldest move I made was embracing surrender after a snowmachine accident, prioritizing my health and peace. My coach showed me "slowing down was the way to speed up," which felt counter-intuitive. This rewired my brain for deeply-aligned thriving, shedding emotional weight and restoring relationships. A surprising lesson is that true change requires confronting what you're "pretending not to know." I realized I was "helping a client hide," not grow. Conventional wisdom might maintain relationships, but I chose clarity, ending the unproductive dynamic. Truth unifies, allowing real progress. Dr. Barbara Eaton, Business Coach, Dr. Barbara Eaton, www.drbarbaraeaton.com
Jeremy Rivera, Co-Founder & Owner, Terp Bros My costliest mistake was thinking my construction background would automatically translate to retail cannabis operations. I underestimated the complexity of cannabis regulations and initially tried to handle compliance solo, which led to a three-week licensing delay that cost us roughly $25K in lost opening revenue. Now I immediately hire specialized consultants for any new regulatory territory--it's always cheaper than the alternative. The boldest move was leaving a stable construction foreman job with zero cannabis industry connections to pursue a CAURD license. Everyone said I was crazy to bet everything on an untested program. That leap of faith made Terp Bros one of Queens' first legal dispensaries and we're now expanding to our second location in Ozone Park. Here's what contradicts conventional wisdom: hire people with criminal records, especially in cannabis. While most businesses avoid justice-involved candidates, I actively seek them out through my non-profit training programs. These employees have incredible loyalty, work ethic, and street credibility that resonates with our community. Our best budtender came straight from my construction training program--customers love his authentic story and expertise. The lesson: your biggest perceived weakness can become your strongest competitive advantage.
Nate Raine, CEO, Thrive; Division Head, Lifebit One costly misstep in Thrive's early years was underestimating the complex web of multi-state regulatory requirements for virtual behavioral health. This forced us to recalibrate expansion plans; now, I'd prioritize comprehensive regulatory expertise much earlier. My boldest move was co-founding Thrive, stepping away from a secure corporate path. Despite initial self-doubt, embracing uncertainty, deeply listening to client needs, and rapidly iterating led to significant growth and expanded mental wellness access. A surprising piece of advice from a mentor was "strategic patience." This counters the 'move fast' mantra, emphasizing disciplined growth by balancing long-term vision with precise short-term execution. It guided Thrive's scaling and Lifebit's complex partnerships.
As the founder of Rocket Alumni Solutions, I've had my share of 'aha' moments learning tough lessons in scaling a software company to $3M+ ARR. One costly misstep in our early years was stubbornly holding onto a feature I was personally fond of, despite clear market signals it wasn't landing. It drained resources and delayed crucial pivots. What I'd do differently now is accept humility faster and scrap ideas mercilessly when data or feedback indicates. Shelving that failing feature eventually freed us to develop our flagship interactive donor wall. Our boldest move that absolutely paid off was allocating budget to build prototypes for an untested market segment in corporate lobbies. This was a significant gamble beyond our initial K-12 focus. That calculated risk secured long-term relationships and expanded our footprint, adding entirely new revenue streams. A surprising piece of advice that contradicts conventional wisdom: share your struggles, not just your wins. It feels counterintuitive, but showing vulnerability about our challenges fosters immense trust with donors and supporters. This authenticity transforms casual supporters into deeply committed lifetime partners, building true loyalty and sustained engagement. Chase McKee, Founder & CEO, Rocket Alumni Solutions, digitalrecordboard.com
**Jessie Eli, Founder, Dermal Era Holistic Med Spa, dermaleraspa.com** My costliest mistake was trying to be everything to everyone when I first opened. I offered every beauty treatment imaginable instead of focusing on what made us different--our trauma-informed, holistic approach. Within six months, I was bleeding money and had zero brand recognition. Now I'd launch with three signature services maximum and build from there. The boldest move that saved my business was starting Woman 360 to mentor other female entrepreneurs while running my spa. Everyone said I was crazy to "distract" myself, but those connections became my strongest referral network. My mentees' clients became my clients, and vice versa--it created this beautiful ecosystem that conventional business advice never teaches. Here's what contradicts everything you'll hear: don't separate your personal story from your business story. I spent two years hiding that I was a single mom building this during custody battles. The moment I got real about my journey, my client base exploded. Women don't want perfect--they want authentic, and they'll pay premium prices for practitioners who've walked through fire themselves.
**Chase McKee, Founder & CEO, Rocket Alumni Solutions, rocketalumnisolutions.com** My costliest mistake was obsessing over product features instead of donor relationships in our first two years. I thought better software would automatically drive growth, but we plateaued around $800K ARR until I started personally calling donors monthly with progress updates and impact stories. That simple shift open uped our path to $3M+ ARR--relationships, not features, drive retention. The boldest move that paid off was scrapping a feature I personally loved because market feedback was lukewarm. Shelving it freed our entire dev team to build interactive donor walls, which became our flagship product and primary revenue driver. Sometimes killing your darlings is the best business decision you'll make. Here's what contradicts conventional wisdom: vulnerability with donors and customers actually builds trust, not weakness. When I started sharing our struggles alongside our wins in monthly updates, donor engagement spiked 25% and referrals jumped 40%. People want to support real humans facing real challenges, not polished corporate facades.
Seth Gillen, Founder & CEO, Sierra Exclusive Marketing, sierraexclusive.com My costliest mistake was initially chasing every digital marketing trend and short-term tactic for quick wins, rather than focusing on foundational, ethical strategies. This led to unstable results and wasted resources. I learned that sustainable growth requires adhering to "white-hat" SEO and building long-term value, which truly impacts ARR for our clients. One bold move that paid off significantly was the strategic adoption and integration of AI tools, specifically custom chatbots, for our clients. There was initial hesitation about automating customer interactions. However, a client's e-commerce site saw their chatbot handle over 500 queries in the first month, boosting sales and reducing support emails by 30%, proving the efficiency and customer satisfaction gains. A surprising piece of advice that contradicts conventional wisdom is to prioritize building "owned communities" over constantly chasing fleeting social media reach. While platforms shift and algorithms change, cultivating direct relationships through email marketing and private groups ensures consistent engagement. Email marketing, for instance, consistently yields a high ROI of $36-$40 for every $1 spent, fostering loyalty beyond volatile social feeds.
As Chase McKee, Founder & CEO of Rocket Alumni Solutions, my costliest mistake was clinging to a product feature I personally loved, despite early market signals it wasn't landing. We wasted resources, but by learning to swiftly scrap such ideas, we developed our flagship interactive donor wall, crucial for our $3M+ ARR. Our boldest move was a calculated risk: allocating budget to prototype for an untested market segment beyond K-12 schools. This gamble paid off, securing long-term relationships in corporate lobbies and expanding our footprint, which became a gateway to new revenue streams. A surprising piece of advice is that authenticity, including sharing struggles, builds stronger relationships. Counter to conventional wisdom, when we entrusted donors with our challenges, their renewed energy and deepened trust solidified our partnerships.
Chase McKee, Founder & CEO, Rocket Alumni Solutions, walloffame.us One costly misstep was prioritizing raw data over individual stories in our early user engagement. I initially missed the qualitative nuances, but shifting to in-person interviews and interactive feedback sessions quickly tripled our active user community, teaching me to embed stakeholder listening deeply from day one. Our boldest move was allocating budget to build prototypes for an untested market segment beyond K-12 schools, specifically corporate lobbies. That calculated gamble paid off significantly, securing new long-term relationships and expanding our footprint into entirely new revenue streams. A surprising piece of advice that contradicts typical startup narratives is to openly share your struggles with your community and donors. Our vulnerability fostered deeper trust, leading to renewed energy and increased support from donors who appreciated our authenticity and built lasting partnerships.
One costly mistake: In my early years at DataNumen, I developed products based on what I thought was innovative—a photo viewer (UniView) and DLL converter—without validating market demand first. Both flopped with minimal sales because I was building solutions to problems that didn't urgently need solving. The boldest move that paid off: After those failures, I pivoted to Advanced Zip Repair for corrupting zip files. Initially, sales were disappointing again. But instead of abandoning it, I invested time analyzing the market and adjusting my approach. That "boring" utility software suddenly generated $2,000 monthly, becoming DataNumen's foundation. Surprising advice that contradicts conventional wisdom: Don't chase the "sexy" innovative product. The market's invisible hand has incredible power—sometimes the most mundane solutions to genuine pain points outperform flashy innovations. My photo viewer was technically superior to competitors, but zip file repair addressed a real, urgent need people would pay to solve. This taught me that successful entrepreneurship isn't about building what you think is cool; it's about solving problems people actually have and will pay to fix. Chongwei Chen, President & CEO, DataNumen Website: https://www.datanumen.com/
In my early days of building our social media presence, I wasted countless hours crafting what I thought were "perfect" posts - meticulously editing captions and creating polished content that ultimately generated zero engagement. My biggest mistake was prioritizing perfection over authenticity, as I quickly learned that audiences connect with real, human voices rather than corporate-sounding messaging. When I finally started sharing genuine thoughts and behind-the-scenes glimpses into our work, our engagement skyrocketed and meaningful relationships with our community began to form. Looking back, I would have saved myself months of frustration by simply being more authentic from the beginning.
One of the most expensive mistakes we made in our early days was relying too much on other companies for our cabinet supply. We started off as a pure online retailer, hoping to build a great business by selling cabinets from companies that were already manufacturing cabinets. What we didn't realize was that we were relying on the manufacturers for quality and performance. When a manufacturer switches to lower-quality materials or completely changes their styles or colors, it is the customer who complains, and sometimes, it is we who deal with the customer's anger. If I could go back, I would have made the decision to open our own manufacturing two years sooner. The boldest decision we made was to stop being a retailer and open our custom cabinetry factory. I remember being told by many people that we were nuts, we were making a huge investment and logistical nightmares, but our customers continued to tell us that they wanted better quality, and size options than those that existed in the marketplace. Taking control of the supply chain was daunting, but it was unbelievably worth it. It enabled us to keep our promise and create high-quality cabinets that were actually made to a customer's vision. It became a competitive advantage, and eventually led to a reputation for quality that became a key part of our growth.
Hi there! I'm Lachlan Brown, co-founder of The Considered Man and founder of a few digital platforms including Hack Spirit. I've been building businesses online for nearly a decade, mostly from cafe tables and coworking spaces around Asia. I've collaborated with FemFounder in good old Haro times and I'm excited to share my insights again on this platform. One of my biggest early mistakes was assuming that growth meant speed. I thought I had to scale quickly — hire early, grab every opportunity, and keep the momentum going at all costs. The result was stress, scattered focus, and systems that weren't ready to handle the load. If I could do it again, I'd move slower and make sure the foundation was steady before building higher. The boldest move I've made? Walking away from a profitable site because it no longer aligned with who I was becoming. On paper, it looked foolish. In practice, it gave me the freedom to create The Considered Man and this site really feels deeply aligned with my values. And here's my surprising advice: don't obsess over passion. Passion ebbs and flows. What matters most is consistency — showing up daily, even when the work feels unglamorous. That's how businesses, and identities, are built. Thanks and don't hesitate to contact me directly if you need more quotes. Cheers, Lachlan
As the Founder & CEO of Sierra Exclusive, having scaled multiple businesses to seven and eight figures, including Fiori Delivery, I've learned many tough lessons in operational structure and revenue growth. My costliest mistake early on with Fiori Delivery was underinvesting in robust automation for order processing and inventory. We relied on manual tracking for too long, leading to fulfillment errors and slower delivery times as order volume surged. I'd now prioritize investing in advanced CRM and logistics software from day one, even if it seemed excessive for initial scale. The boldest move I made was launching Fiori Delivery with aggressive daily discount programs, like 20% off specific product categories *every day of the week*. This seemingly risky strategy paid off by driving significant repeat business and cultivating a highly loyal customer base who actively anticipate our deals. Conventional wisdom often preaches strict margin protection, but my surprising advice is to prioritize customer lifetime value over immediate per-transaction profit. By consistently offering deep discounts and free delivery, we've built incredible loyalty and word-of-mouth for Fiori, turning one-time buyers into regular, high-value customers. Seth G, Founder & CEO, Sierra Exclusive, Fiori Delivery, fioridelivery.com