40+ entrepreneurs share what they’d do differently if starting over: build systems sooner, delegate earlier, focus on niches & trust instincts.
When starting a business, you’re going to make mistakes, but you can’t see them clearly until you’re looking in the rearview mirror.
I reached out to more than 40 successful entrepreneurs with one simple question: “If you could go back and start your business all over again, what would you do differently and why?”
Their answers reveal the hard-won wisdom that only comes from building something from scratch.
From focusing too early on growth to waiting too long to delegate, these founders share the pivotal lessons they wish they’d learned on day one.
The Brutal Truth: What 40+ Business Owners Wish They’d Known on Day One
If I could do things differently, I would prioritize cultivating stronger connections with other professionals in the industry. I was so focused on making sales and closing deals that I neglected to nurture connections with fellow realtors, mortgage brokers, contractors, and other key players in the industry. I now understand the importance of having a network of trusted colleagues to collaborate with and refer clients to. Building these relationships not only helps in business growth but also creates a sense of community within the industry.
We run an eight-office law firm that we built in under ten years. The pace has been hectic! The main thing I would have done differently to have made it less stressful, and probably led to even faster growth, is spend more time on projecting the firm’s production and financial metrics. Coupled with this, I would have critically analyzed where my calculations were wrong to get a better understanding of how the firm is really performing and how we can improve. We are significantly better at these skills now, and it leads to much better decisions.
I would’ve focused on building a repeatable service offering sooner. Early on, we tried to be everything to everyone—custom projects, every platform, all industries. It stretched the team thin and made it hard to forecast revenue or scale without burning out. What changed the game was when we doubled down on content and SEO for local service businesses. We built templates, processes, and a pricing model that didn’t require reinventing the wheel every time. It made onboarding faster, quality more consistent, and margins healthier.
I think many early-stage founders fall into the same trap—chasing flexibility instead of focus. You want to say yes to everything because you’re trying to grow, but in reality, it muddles your positioning and eats up your resources. The moment we became clear on who we serve best and how we solve their problems, everything became easier—from marketing to hiring to retention. That’s the piece I’d lock in on day one if I were doing it again.
We’d focus even earlier on educating homeowners, not just connecting them with quotes. In the beginning, we were laser-focused on simplifying the quote comparison process, which we still believe is critical. But we’ve learned that many people come to us feeling unsure, not just about which provider to choose, but about the basics of how solar works, what incentives apply, and whether it’s really right for their home. If we had built our education tools right from day one, we could’ve empowered more homeowners from the start to make confident, informed decisions.
We’d also invest sooner in better vetting standards for our installer partners. Over time, we’ve fine-tuned how we evaluate companies, looking beyond pricing and panels to long-term customer care and service quality. That shift came through experience, but had we nailed it from the outset, we could’ve saved some early users from less-than-stellar experiences.
Still, those lessons shaped who we are today. We’re more than a quote comparison site. We’re a trusted guide in an industry that can feel complicated and crowded. If anything, we’d just speed up the evolution that brought us here.
If I could go back and start Thor Metals Group all over again, I’d spend more time early on building deeper relationships with our clients and partners. In the early days, I was so focused on growth and operations that I sometimes missed the bigger picture of long-term trust. Precious metals are a relationship business. People aren’t just buying gold; they’re investing in security, legacy, and a sense of peace of mind. Looking back, I would have spent more time listening, understanding individual goals, and tailoring solutions with even greater care. That foundation pays dividends far beyond any marketing campaign.
I also would’ve brought in a more diverse team sooner. Different perspectives sharpen strategy and reveal risks before they become problems. It’s something I came to value deeply as we grew, but in the beginning, I leaned too heavily on familiarity rather than seeking out those who could challenge me.
Ultimately, every mistake taught me something valuable. But if I could fast-track one lesson, it would be this: relationships and perspective drive sustainable success. The gold itself is just the medium. The real asset is trust, and that’s built through people, not just products. That’s the part I’d start with from day one.
If I could go back and start Bestonlinecabinets all over again, I would prioritize securing our manufacturing capabilities even earlier in our journey. While we initially focused on curating high-quality cabinets from established brands, it became clear that having our own manufacturing would not only enhance our product offerings but also give us greater control over quality and pricing. The feedback from our customers about wanting more customized options was invaluable, and had we acted on that sooner, we could have carved out our niche in the market more quickly.
I would invest more in building relationships with our suppliers and logistics partners right from the start. Strengthening these connections early on would have streamlined our operations and helped us better navigate the complexities of the supply chain as we grew.
I’d focus less on looking polished and more on building trust early. Time went into the wrong things, branding, perfect messaging, and unnecessary details. What helped most was showing results. That builds credibility faster than any design or tagline. If I were starting again, I’d lead with proof, not presentation.
I took on too much work that didn’t fit. Saying yes felt like progress, but it pulled the business in too many directions. Focus wins. The clearer the offer, the easier it is to grow. I’d stay narrow, build consistency, and only take on work that supports long-term goals.
Efforts also went into the wrong channels. Not every platform or tactic needs attention. A few strong wins beat constant noise. Publishing meaningful content, staying consistent, and building real relationships outperformed everything else. I’d stop chasing trends and double down on what works.
The biggest shift would be moving faster on what matters and cutting the rest.
If I could go back and start Kate Backdrops all over again, I would focus earlier on building a strong, customer-centric culture. While we ultimately grew to prioritize our clients’ needs, starting this from day one would have accelerated our ability to adapt to their evolving preferences and provide unparalleled service.
Also, I would invest sooner in scalable technology to streamline operations and enhance product quality. These proactive steps would have positioned us to grow even faster and respond to market demands with greater agility.
I would rethink who I learned from. Full transparency, I’m a creative woman in her 20s who built her business from scratch. From the beginning, I should have been learning from people who were similar to me. As in, why was I hiring people twice my age to teach me stuff, when they weren’t even creative business owners?
There’s a misconception that “business” needs to be really professional, buttoned-up, and stale. I was trying to fit into that mold when I first started. Now? My business is completely free-flowing, creative, and fun (and so are my clients.) I only wish I started building that for myself sooner.
If I could start my business over, I’d focus much earlier on building systems and processes instead of trying to do everything myself. Early on, I wore too many hats, which slowed growth and led to burnout. Investing in the right tools and delegating sooner would have freed up time to focus on strategy and scaling. I’d also prioritize customer feedback earlier, using it to shape offerings instead of guessing what the market wanted. These changes would have saved time, reduced costly mistakes, and accelerated growth. Learning to balance action with planning is one of the most challenging yet most valuable lessons I’ve learned. Starting smarter, not just harder, makes all the difference.
I’d invest in a mobile showroom from day one. Too many customers struggle to envision how flooring looks in their homes versus our bright showroom. After seeing countless customers make decisions they later regretted, I realized we needed to bring the showroom to them. Now our sample delivery service solves this, but a mobile unit would have saved years of customer disappointment.
If I could go back and start Aura all over again, I’d spend more time upfront building the right team and getting clearer on what kind of culture I wanted to create. In the early days, I was so focused on getting the business off the ground that I underestimated how important the people side of things would be. The right team doesn’t just execute your vision, they shape it, challenge it, and often make it better. I’d also be quicker to trust my gut. There were moments I second-guessed myself, especially when the stakes felt high, but I’ve learned that instincts honed by lived experience are usually pointing you in the right direction. Looking back, I also think I’d be less afraid of saying no. Opportunities come along that seem great on paper but can pull you away from what really matters. Staying focused on Aura’s mission to bring more humanity and care into funeral services is what’s helped us grow in a meaningful way. I’m proud of what we’ve built, but there’s always something to learn. If I had the chance to do it again, I’d lean into those lessons sooner and trust that staying true to our purpose is what drives everything else.
If I could start over. I would have made assembling a more specialized, cohesive team my first priority right away. I took on too many roles in the beginning. This caused decision-making to lag and made it harder to distinguish between doing and leading. Delegating was about having a system, not about losing control. I would have had more time to concentrate on expansion and long-term planning if I had brought in professionals sooner.
I also would have invested earlier in scalable systems. When you’re starting out, it’s tempting to patch things together with tools that just get the job done. That works until it doesn’t. We spent time rebuilding processes that could have been set up right the first time with a clearer view of future growth. Looking back, I underestimated the value of a strong operational backbone.
What I wouldn’t change is the mission. That has always been clear and rooted in something deeper than revenue. The work has always been about access, dignity, and removing barriers to care. Starting a business in the health space demands focus and flexibility. You learn fast what matters most. Those early missteps were necessary. They sharpened my ability to lead with intention and made the foundation stronger than I ever expected.
Corina Tham, Sales, Marketing and Business Development Director, CheapForexVPS
If I could restart my business journey, I would focus on establishing a solid base in trading methodologies and technological adaptation from the outset. When I initially launched, I wasted too much energy trying to perfect minor details instead of concentrating on scaling the core elements that truly matter, such as ensuring customer satisfaction and creating a reliable infrastructure. I would have placed greater emphasis on understanding my audience and tailoring CheapForexVPS’s offerings to their specific demands from day one.
Another major shift would have been to implement SEO and online marketing techniques earlier to foster organic traction, as these have become pivotal in my work as a Sales, Marketing, and Business Development Director. I’ve come to realize the value of introducing automation systems early in trading operations to optimize time and resources. Cultivating meaningful networks with clients and collaborators would also have been higher on my priority list—these relationships have significantly influenced my career achievements.
Lastly, I would strive to balance innovation with practicality; often, straightforward approaches yield the best results in both trading and business growth. These lessons have shaped how I now seamlessly integrate my trading knowledge with modern strategies to deliver outstanding results.
I would slow down and focus before growing. In the beginning, I moved fast without strong systems or structure. That led to mistakes and unnecessary setbacks. A smaller, stable foundation would have delivered better results. Growth works best when built on consistency and discipline.
I’d also say no more. I wasted time and resources on things that didn’t support the mission. Not every opportunity is worth it. Now I ask one question. Does this help the team, the client, or the community? If not, I move on.
I’d take better care of myself, too. I pushed through stress and skipped rest. That hurt my leadership. Your business reflects your energy. If you’re off track, so is your team. Before building bigger, make sure you’re building right.
If I could go back and start Ozzie Mowing & Gardening all over again, one thing I would do differently is invest earlier in building a strong network of reliable suppliers and skilled subcontractors. In the early days, I tried to handle too much on my own, which stretched me thin and occasionally impacted the speed of service delivery. Once I started leaning into the connections I’d built over the years working in the industry and backed that up with my horticultural training, I was able to partner with people who shared my standards and values. That shift allowed me to focus more on designing, planning and delivering high quality results for my clients, while trusting others to support with materials and specialised tasks.
A great example of this was a large landscaping job for a client who needed a full garden transformation, including native planting, irrigation and paving. Thanks to my qualifications as a horticulturist, I was able to create a planting scheme that suited the soil and sun exposure perfectly, but it was my relationships with trusted trades and my experience managing over 700 projects that helped me coordinate everything seamlessly. The job was completed ahead of schedule, the plants thrived, and the client ended up hiring us again for ongoing maintenance. That project was a clear turning point where I saw the value of leaning on both experience and professional networks to get the best outcome.
When I first started my business, I underestimated the importance of a solid business plan. I jumped in based on passion alone, which, don’t get me wrong, is crucial, but it’s like setting sail without a map. This time around, I’d definitely spend more time planning, especially focusing on the financial forecasts and market research. It’s these blueprints that help anticipate hurdles and keep you on track financially.
Another thing I’d change is how I approached marketing. Initially, I relied too much on word of mouth and underestimated the power of social media and online marketing. If I were to do it over, I’d invest in a good marketing strategy right from the start. Engaging with potential customers on multiple platforms can really boost your business’s visibility and growth. Always remember, knowing your audience and where to find them is half the battle won.
If I could go back and start Zapiy.com all over again, I’d do one thing much sooner: get crystal clear on the problem we were solving—and for whom.
Like many early-stage founders, I made the classic mistake of building too fast without enough friction. We had a great product idea, a talented team, and plenty of momentum. But we didn’t spend enough time deeply validating our core assumption: does this solve a painful enough problem that people are willing to pay for it, today—not in theory, but in practice?
Looking back, I would’ve slowed down just enough to double down on customer discovery—real, unfiltered conversations with our target users, before a single line of code was written. I would’ve asked harder questions, been less attached to our original vision, and more open to pivoting early. That would’ve saved us from some expensive detours and a few months of building features no one truly needed.
I’d also invest earlier in brand and content. Not just SEO or performance marketing, but building trust through thought leadership and storytelling. People don’t buy just for features—they buy from companies they believe understand them. That trust compounds over time, and I underestimated its long-term value in the beginning.
Lastly, I would’ve prioritized hiring people not just for skills, but for mindset. In the early days, attitude and adaptability beat resume credentials every time. The right people don’t just do the job—they shape the direction.
Starting a business teaches you fast, but in hindsight, alignment—between product, people, and purpose—is where the real leverage lives. And the sooner you find it, the stronger your foundation becomes.
If I could start Fulfill.com over again, I’d focus on three key areas that would have accelerated our growth and reduced growing pains.
First, I’d build our technology infrastructure with greater scalability from day one. When we initially connected eCommerce brands with 3PLs, our matching process was more manual than I’d like to admit. Having experienced the challenges of scaling tech systems firsthand, I’d invest more upfront in flexible architecture that could accommodate rapid growth without requiring constant rebuilds.
Second, I’d establish more comprehensive vetting procedures for our 3PL partners earlier. This insight comes directly from my own journey—before Fulfill.com, I ran my own 3PL called ShipDaddy after experiencing frustration with three different fulfillment providers for my eCommerce board game business. I intimately understand what makes a great 3PL partner versus a mediocre one. The more rigorous our selection process, the better outcomes for our clients.
Finally, I’d focus on educating the market sooner about the strategic importance of fulfillment. Many businesses view logistics as a cost center rather than a competitive advantage. Having witnessed countless brands transform their growth trajectory with the right fulfillment partner, I know this mindset shift is crucial.
What I wouldn’t change? Starting this business in the first place. The logistics space is filled with complexity and frustration—that’s precisely why connecting brands with the right partners matters so much. When I was shipping board games from my parents’ garage before scaling to a 140,000-square-foot warehouse, I experienced firsthand how the right fulfillment strategy can transform a business.
The most rewarding aspect of building Fulfill.com has been seeing brands find partnerships that unlock their potential, something I wish I’d had when I was in their shoes.
I’d focus earlier on building alignment across teams. In the beginning, departments moved on different timelines and priorities. This created confusion, delays, and missed opportunities. When teams stay disconnected, problems stack up, and progress stalls. Setting clear routines for communication would save time. Quick, focused check-ins help teams move with purpose and reduce friction across the board.
I’d also avoid chasing too many ideas at once. Adding features or options without clear value only drains resources and slows momentum. Without focus, execution slips. Some projects never finish. Others don’t solve real problems. Keep the basics strong and make sure they work. That drives better results over time.
Growth comes from focus, clear feedback, and steady execution. Most problems come from mixed priorities or weak communication, not missing skills. When alignment is strong, execution becomes sharper and faster. Fixing root problems early reduces waste, builds trust, and keeps teams moving forward with confidence.
If I could go back and start Green Lion Search all over again, I’d trust my instincts more, and waste a lot less time chasing reassurances.
In the early days, I second-guessed a lot. I’d have a gut feeling about a candidate, a client fit, or even a business decision, and instead of acting on it, I’d go looking for validation: more data, more opinions, more consensus. It felt like the responsible thing to do, but in reality, it often just slowed me down or diluted my direction.
What I thought was impulse was actually highly informed by experience, and more often than not, my initial instinct was the right move. The real risk was letting the opportunity blow past me while I was double-checking my due diligence.
So, if I were doing it again, I’d move faster and with more confidence.
That’s not to say I’d throw strategy out the window. But I’d give more weight to my own perspective early on, rather than looking outward.
I did not realize how complicated compliance could be. I would have involved legal and regulatory experts from day one. Handling extra medical stock is not just about storage or shipping, it also involves laws, ethics, and different rules in each area.
We made some mistakes at first, but they taught us a big lesson: having clear and complete records is not just a formality. It builds trust, shows you are serious, and helps avoid future problems. Now, we document everything carefully, and that simple change has greatly impacted how we are seen.
If I could go back and start Miller Pest & Termite all over again, I’d invest in building a better hiring and training system from day one. In the early years, I focused almost entirely on expanding our customer base—adding more routes, more trucks, and more calls. But I didn’t put the same energy into building the right team structure. We’d hire fast when things got busy, throw new techs into the field with a short ride-along, and hope they figured it out. Some did, but we lost a lot of good people who could have stayed if they’d had better onboarding.
That gap hit hard when a couple of senior techs left in the same month and I realized how much institutional knowledge walked out with them. Since then, we’ve built a training program that includes a mix of fieldwork, shadowing, and check-ins throughout the first 90 days. It’s made a massive difference in retention and consistency. Looking back, I wish I’d realized earlier that growth without strong people systems underneath it is just a mess waiting to happen. You can always sell more work, but if you can’t deliver it well, it won’t last.
If I could start over, I’d focus on making sure every tech effort connects to a clear business goal. Many teams jump into tools too fast and lose sight of results. That wastes time and slows progress. When you start with the outcome, teams move faster and make better choices.
I’d also bring in experienced leaders earlier. Early on, we relied on people doing too many things. That made decisions slow and messy. Once we had experts focused on key areas like security and operations, things improved fast. Clear roles and ownership made the work smoother.
I’d also change how we measure work. Charging for hours doesn’t always lead to results. Tying work to impact builds trust and pushes everyone to focus. It’s better for clients and the team.
Starting strong matters. When you focus on outcomes, bring in the right people, and track real results, everything moves forward with less waste.
This is a great question. I am so pleased with where we are today, so I wouldn’t want to change much, however if I had to do something differently, I think I would expand my team earlier. We had a very small team for a while, and because of that I remember feeling pretty overworked and burnt out, having to take on so many responsibilities. I think I waited a bit too long to expand the team simply because I was afraid of accidentally doing that prematurely, but I definitely could have done it earlier and we would have all benefited from that.
I’d bring in operational support earlier and stop trying to do everything myself.
In the first year, I handled every detail. Scheduling, compliance checks, quoting, customer service, stock, and fleet. That kept things tight but slowed growth. I thought staying hands-on meant staying in control. It didn’t. It meant firefighting. Once I hired support staff to manage scheduling and admin, engineers had fewer delays, customers got quicker updates, and I had time to focus on planning and strategy.
I also waited too long to invest in better systems. We used spreadsheets, emails, and paper files far longer than we should have. Job tracking was slow. Communication was messy. Switching to a central system gave everyone real-time visibility. Engineers, office staff, and clients worked from the same data. That reduced mistakes, saved time, and improved service. That change should have come in month six, not year two.
I would have been more selective with projects. We said yes to everything at the start. That included jobs outside our strengths. They added pressure, dragged timelines, and hurt team morale. Focusing only on work that fits our expertise helped us serve clients better and keep quality high.
If I started again, I’d ask for help sooner, simplify our systems, and say no more often. You need to protect your time and energy from day one. What task are you doing right now that someone else should own? That’s where to start.
If I had the chance to start over, I would focus more on learning what HVAC customers need in different parts of the country. The country is large, and the weather varies a lot. What sells well in a hot and humid place might not work in a cold place, and what works in a rainy place does not work in a hot place.
Back then, my team and I treated the HVAC market as one big group, which slowed us down. Planning our inventory and marketing based on local climates would have helped us connect better with customers and avoid wasted stock. It is a simple change that could have made us faster and more focused from the start.
If we had to start over, we would plan with more flexibility in mind. The land taught us to be patient, but the market moves fast. We did not realize how quickly customer needs and habits would change.
Now, we are quicker to adjust, like setting up a drive-thru or changing how we run farm tours for school kids. In the past, we focused on building something steady and strong. But looking back, we see that being more open to change early on could have helped us grow faster and stay better connected with the people we serve.
I have gained valuable experience and knowledge over the years that has helped me grow my business. However, there are always things we wish we could do differently if given the chance. Reflecting on this question, there are a few key areas where I would make changes to my approach.
Also, I would place more emphasis on building strong relationships with clients from the very beginning. While delivering results is important in any business, establishing trust and rapport with clients is crucial in the real estate industry. It not only leads to repeat business and referrals but also creates a positive reputation for your brand.
I would also focus on implementing effective systems and processes right from the start. As the market is ever-changing, having a solid foundation of systems in place can help streamline operations and adapt quickly to new market trends. This could include using technology for efficient communication, task management, and data analysis.
If I could rewind and do it all over, I’d focus less on services and more on productized offerings from day one. In the early years, we said yes to everything—custom campaigns, one-off projects, messy scopes. It got us work, but it also burned time and blurred our positioning. Clients didn’t always know what we stood for, and neither did we.
Looking back, the smartest move would’ve been packaging what we were best at—like SEO audits or social content plans—into clear, repeatable products. It would’ve saved countless hours on proposals, reduced scope creep, and built brand clarity much faster. That structure now lets us scale without losing our sanity. So if you’re just starting out: make it easy for clients to understand what you do and how they can buy it.
Kevin Heimlich, Digital Marketing Consultant & Chief Executive Officer, The Ad Firm
If I could go back and start The Ad Firm all over again, the very first thing I’d do differently, without a doubt, is specialize much earlier. When I first started out, especially fresh off my real estate experience and seeing the possibilities of digital marketing, my natural instinct was to say “yes” to every single client opportunity that came our way. We truly tried to be everything to everyone.
The problem with that approach, I quickly learned, is that it really dilutes your expertise. It becomes much harder to genuinely stand out in a crowded market when you’re trying to master every single facet of digital marketing for every single industry. If I had a do-over, I would choose a specific niche from the beginning, such as B2B SaaS lead generation or e-commerce conversion for a particular product type, and then dedicate all our energy to becoming the undisputed experts in that one area. Focusing like that not only attracts higher-value clients who specifically need your precise expertise, but it also makes your marketing efforts so much simpler and more powerful. It truly defines who you are and what you do best.
If I could hit reset, I’d focus on building an audience before building offers. In the beginning, I spent too much time perfecting services and systems, assuming “if it’s good, they’ll come.” They didn’t; at least not fast.
What I’d do differently is start creating value-driven content from day one: case studies, behind-the-scenes breakdowns, even quick wins on LinkedIn or email. That early visibility compounds faster than any cold outreach.
The biggest lesson? Trust builds before sales happen. If people know your voice, see your thinking, and get consistent value, the business part comes much easier and with fewer awkward pitches.
If I could start over and rebuild my business from scratch, I’d make one major change: I’d quit jumping from idea to idea and commit fully to one venture. Looking back, it feels like such an obvious choice—but at the time, each new concept felt like the one. I wasn’t just chasing trends for fun—I genuinely believed I was being creative and flexible. But what I didn’t realize was that spreading my focus so thin was slowing me down far more than it was helping me move forward.
In reality, I was splitting my focus, scattering my energy, and diluting the impact I could’ve made by staying the course with a single, well-chosen path.
At the beginning, it’s easy to get swept up in the thrill of new ideas. Everything feels wide open—you’re free to explore, driven by curiosity, and surrounded by endless inspiration just a click away. That kind of energy is electric. It makes you feel like anything’s possible.
But here’s the problem: switching from one concept to another—before the first even takes root—leads to a cycle of false starts. I wasn’t giving any of my ventures the time or focus they deserved to flourish.
What I’ve learned is that mastery takes time. Markets don’t reward dabblers—they reward depth, resilience, and consistency. If I’d picked one idea and nurtured it through the hard, messy middle, I would’ve built not just a product or service, but a brand with a voice, an audience, and momentum.
The magic happens when your energy isn’t constantly resetting. It compounds. With a single venture, you can streamline your processes, build trust with your audience, and refine your offer based on real feedback—not hypothetical possibilities from a pivot that came too soon.
So if I could go back, I wouldn’t brainstorm more—I’d build more. I’d plant one flag and defend it. Because real growth doesn’t come from trying everything. It comes from showing up for one thing, every day, until it works. And if that isn’t the heart of entrepreneurship, I don’t know what is.
If you’re in the middle of choosing between ideas, let this be a nudge: pick the one that won’t leave you alone and go all in. You’ll thank yourself later. I know I would.
I would start with more focus and patience.
In the early days, the goal was fast growth. More work, more clients, more activity. That led to scattered priorities and uneven results. If I start again, I’d take it slow and focus on basics. Set standards. Stay consistent. Take on the right opportunities, not every opportunity. Growth without structure creates more problems than progress.
I’d also pay closer attention to how things operate behind the scenes. Too much depended on one person doing too many things. That created pressure and weak points. I would’ve built better systems earlier. Defined roles. Clear processes. Routines that made the day smoother. Once those were in place, everything from client service to job performance improved.
Marketing needed the same shift. I believed good work would speak for itself. But visibility matters. People search online. They check reviews. They want proof. I would’ve focused sooner on showing that work—sharing results, staying active online, and building trust through consistent messaging. You don’t need a large reach to make a strong impact. You need to show up where it counts.
If I could rewind the clock and start over, I’d spend more time upfront building a tighter alignment between strategy and execution. Early on, I was so focused on big-picture growth, the deals, the partnerships, the capital, that I occasionally underestimated how critical it is to have every team pulling in the same direction from day one. I’ve learned that momentum is fragile. It doesn’t matter how strong the strategy looks on paper if the execution lacks clarity or buy-in. I’d also put more emphasis on culture as a strategic asset. In high-growth or turbulent markets, culture isn’t just a feel-good factor, it’s what holds everything together when things get messy. Finally, I would’ve said “no” more often. Not every shiny opportunity is the right one, and learning to focus on fewer, higher-impact moves earlier would’ve saved time, money, and energy. That said, I don’t believe in regrets. Each misstep taught me something I’ve carried into future partnerships and investments. The messiness is part of the process. But if I were starting fresh, I’d walk in with sharper focus, tighter alignment, and a much clearer sense of what actually moves the needle.
If I could start Estorytellers all over again, I’d invest earlier in systems and delegation. In the beginning, I tried to do everything myself—from client calls to backend operations—which slowed growth and led to burnout.
I’ve learned that building a solid team and trusting them with responsibility frees up your time to think bigger and lead better. I’d also focus more on building community and brand storytelling from day one, not just conversions. That emotional connection with clients is what drives long-term success in our business.
My advice is to prioritize people and processes early. It makes the journey smoother and the impact stronger.
If I could go back and start Apps Plus all over again, I’d focus earlier on narrowing our niche. In the beginning, we tried to serve everyone, which diluted our impact. It wasn’t until we got really clear on who we were best positioned to help that things accelerated. I’d also invest in building out our leadership team sooner. I spent too much time in the weeds early on, which slowed our growth. Having the right people in the right roles not only freed me up to focus on strategy but also created space for the business to mature faster. Another big one would be prioritizing partnerships. The tech world moves fast, and collaborating with the right partners opens doors you simply can’t force open alone. I learned that the hard way, trying to build too much in-house when collaboration would have been a smarter move. Still, I don’t regret the journey, it taught me the value of focus, trust, and knowing when to let go. If anything, starting again would just mean accelerating what I now know works. Clarity, talent, and connection aren’t just nice to have. They’re what move the needle. And I’d double down on all three from day one.
If I had a do-over with Lindenwood, I’d lock down our internal systems way earlier—things like onboarding flows, campaign checklists, and reporting frameworks. In the early days, we relied on instinct and hustle, which got the job done but made everything slower and more stressful than it needed to be.
Once we finally built out clear processes, we saw immediate lift: fewer missteps, faster turnaround, and a better experience for clients and team alike. It turned chaos into consistency.
Bottom line: your talent gets you started, but your systems are what let you scale. Build them sooner than you think you need to.
I’d invest in building stronger systems from day one. In the early years, everything lived in my head—routes, pricing, how we handled certain pests. That worked when it was just me and maybe one other tech, but once we started growing, things got messy fast. I recall that once, we double-booked three appointments on the same day because there was no shared calendar. It made us look unprofessional and stressed the team out. If I’d taken the time early on to set up better processes, we could’ve scaled smoothly and saved ourselves a lot of headaches.
What I’ve learned is that structure doesn’t kill flexibility—it enables it. When your team knows where to find information, how to handle issues, and what’s expected, they’re more confident, and you’re less tied to the day-to-day. So if I had to start from scratch, I’d map out those workflows, even if they seemed basic at the time. You can always adjust as you grow, but you can’t retroactively install a foundation once things are already moving too fast.
If I could start over, I’d invest in stronger financial ops from day one. Early on, we focused so much on product and sales that we treated budgeting like an afterthought. I remember scrambling to figure out burn rate during our first real cash crunch—it was avoidable, and it distracted us at a critical growth point.
Since then, we’ve built out proper forecasting and scenario planning, even for small decisions. If I had done that earlier, we could’ve scaled cleaner and with less stress. It’s not the flashiest part of running a business, but it’s what keeps the lights on when things get messy.
If I could start over, I’d invest earlier in customer onboarding and success—not just as a support function, but as a growth engine. In our first year, we were so focused on acquiring new clients that we treated onboarding like a checklist instead of a strategic moment. We’d hand off the product, send some docs, and move on. But looking back, we missed a huge opportunity to build stickiness early. The turning point came when a long-time customer churned and cited confusion about feature value—something that could’ve easily been addressed in week one.
Now, we treat onboarding like a campaign. We map out the first 90 days with intentional milestones, proactive check-ins, and even tailored mini-trainings. It’s not just about making sure users can log in—it’s about getting them to their first “aha” moment fast. If I had understood sooner how closely retention ties back to that early experience, I would’ve built the function from day one, not retrofitted it after mistakes.
I’d invest in building a real sales engine much earlier. For the first couple of years, we relied almost entirely on referrals and word of mouth. It worked fine—until it didn’t. When deal flow slowed, we had no outbound strategy, no CRM hygiene, and no clear offer that someone could sell if it wasn’t me. I didn’t think of sales as a system; I thought of it as something I just had to do when needed.
Looking back, we could’ve grown faster and with less volatility if we’d treated sales like a product—something to refine, test, and operationalize. Now we’ve built that engine, and it’s changed everything. It’s not about being aggressive—it’s about being intentional. If you’re starting out now, don’t wait for the referral train to run out of steam before you figure out how to sell. Build the process before you need it.
I would’ve documented our processes from day one. In the beginning, it felt easier to just show someone how to do something in person or explain it on the fly. But as we grew and added more techs, that approach fell apart fast. Everyone started doing things a little differently—treatment methods, how they talked to customers, even how they stocked their trucks. It wasn’t until we had a few service missteps and some uneven reviews that I realized we needed clear, repeatable systems.
Looking back, building those SOPs earlier would’ve saved us a lot of headaches. It’s not just about consistency—it’s about giving your team the confidence that they’re doing it right. Now we’ve got a shared digital handbook, short training videos, and service checklists that new hires can rely on. My advice to any new owner? Don’t wait until things break to systematize. Build it while it’s small, and scaling becomes a whole lot smoother.
I’d focus on building out our internal systems and documentation earlier. When we first started, everything was stored in my head—routes, customer notes, treatment preferences, and billing quirks. That worked fine when it was just me or a couple of guys, but as we grew, it created confusion and bottlenecks. People had to come to me for answers constantly, and that slowed everything down. It wasn’t scalable, and I didn’t realize how much that would hold us back until we were already feeling the pain.
Looking back, I would’ve taken the time to document processes, create checklists, and invest in software that could grow with us. Having that structure from the start would’ve saved us from a lot of trial and error—and probably a few frustrated employees. The lesson I learned is that hustle can only take you so far. If you want a business that lasts, you have to build a foundation that lets other people succeed without you standing over their shoulder every day.
I’d invest in building a stronger customer onboarding system from day one. In the early stages, we were so focused on selling that we treated onboarding as a checklist—get the contract signed, hand them a setup guide, move on. What we didn’t realize was how much churn we were creating just by not holding their hand through those first few weeks. One client even told us, “I wanted to love it, but I never really figured out how to use it.” That hit hard.
Looking back, I would have built onboarding as a product in itself: structured milestones, proactive check-ins, and a dedicated team to guide customers through early value. It would have saved us months of rework and rebuilt the trust we lost early on. The lesson? Retention starts before the first renewal. If your customers don’t feel successful fast, you won’t keep them long enough to fix it later.
How Would YOU Start Over If You Could?
The patterns in these responses are striking. Whether running a pest control company, a tech startup, or a marketing agency, successful entrepreneurs consistently wish they had built stronger foundations such as better systems, clearer processes, and more focused strategies from day one.
The most repeated themes? Stop trying to do everything yourself, narrow your focus instead of chasing every opportunity, and invest in the unglamorous backend work that actually scales a business.
As Richie Gibson put it perfectly: “Real growth doesn’t come from trying everything. It comes from showing up for one thing, every day, until it works.”
If you’re just starting your entrepreneurial journey, take these lessons to heart. You don’t have to learn everything the hard way. Sometimes the best business advice comes from those brave enough to admit their mistakes, and generous enough to help you avoid making the same ones.
