a day ago
20 things biz leaders wish they had done differently from the start
Hindsight can be a powerful teacher, especially for entrepreneurs who've weathered the highs and lows of building a business from the ground up. From financial decisions and branding strategies to selecting the right partners and saying 'no' sooner, many business leaders have learned what they'd do differently if they had the chance to start fresh.
To that end, Fast Company Executive Board members reflect on 20 hard-earned lessons and share the changes they'd make if they were launching their companies today. Here's how they've used what they've learned as a valuable roadmap for building stronger, more resilient companies.
1. START TAKING A PAYCHECK SOONER.
There is no doubt in my mind that I would start to pay myself much sooner than the first time around. I sacrificed a lot and realized after the fact that taking care of my finances first sets the business up for more success faster. – Mike Rizzo,
2. BUILD SELF-SERVICE DATA INFRASTRUCTURE EARLY.
I would focus on building a data infrastructure with more emphasis on self-service analytics. We realized over time how critical it is, not only for business decisions, but for continuously improving the student experience. I'd invest in systems earlier that let us measure and act on learning outcomes with more precision, without constantly invoking analysts to code dashboards in SQL. – Max Azarov, Novakid Inc.
3. DEVELOP THE BRAND PUBLICLY FROM DAY ONE.
If I were starting from scratch today, I'd build the brand in public from day one—sharing the process, the pivots, and even the ugly parts. For too long, I focused on outcomes instead of letting people in on the journey. However, I've learned that showing your work builds trust faster than polished metrics ever will. – Reuben Yonatan, CX Foundation
4. SECURE MORE LIQUIDITY AND CAPABLE PARTNERS UPFRONT.
I would secure ample liquidity through various financial instruments, such as credit cards and lines of credit. I'd also strategically partner with one or two capable individuals to effectively share operational responsibilities and mitigate the pressures associated with launching a new business. – Martin Pedersen, Stellar Agency
5. PRIORITIZE SCALABLE OPERATIONS FROM THE BEGINNING.
If I could start from scratch today, I would make sure to think long-term about operational efficiency to create and streamline internal processes in a more scalable way. By doing so, this action would have saved time and supported faster, more sustainable growth as our client base expanded and their security needs evolved. – Justin Rende, Rhymetec
6. INVEST IN THE RIGHT TEAM RIGHT AWAY.
When you first start a business, you are focused on saving every dollar. One thing I would have done differently would be to invest in a great team right away. Yes, it may cost more, but it will end up saving you time and making you more money in the long run. Invest in your people, and they will take care of the rest. – Victoria Chynoweth, Victoria Chynoweth
7. DEFINE CORE COMPANY VALUES EARLY ON.
I would implement foundational company values from the start. By establishing clear pillars, leaders can define what drives their purpose and passion, and align those values with business objectives. It also gives employees a solid foundation to lean on, fostering a stronger sense of community, collaboration, and purpose beyond daily tasks. – Tom Amburgey, Euna Solutions
8. CHOOSE A BUSINESS-SAVVY PARTNER OVER AN INDUSTRY PEER.
I would partner with someone who knew business, not someone who knew the same industry I did. Anyone can start a business. There are some non-obvious things about staying in business that I had to learn over time. – Bob Sprague, Yes&
9. BUILD AN AUDIENCE BEFORE LAUNCHING.
If starting over, I'd build an audience first—sharing valuable content to grow trust and demand before launching. This approach validates the idea early, attracts feedback, and reduces marketing costs later. – Scott Keever, Keever SEO
10. CRAFT A STRONG BRAND NARRATIVE FIRST.
I would invest earlier in building a strong brand narrative. In the beginning, I focused heavily on execution—getting deliverables out the door—without fully defining what made us different. A clear, compelling story would have helped attract better-fit clients, talent, and partnerships from day one. – Maria Alonso, Fortune 206
11. DESIGN FLEXIBILITY INTO THE BUSINESS MODEL.
Prioritize building flexibility directly into the core business model from day one. Rather than focusing exclusively on long-term fixed strategies, adopt a lean, iterative approach—quickly testing and learning from early customer feedback. Embracing this mindset from the start would position the business to swiftly adapt, grow sustainably, and stay resilient in an evolving market environment. – Britton Bloch, Navy Federal Credit Union
12. FOCUS ON REAL CUSTOMER PAIN POINTS.
I would place greater emphasis on being customer-centric from day one. If we had truly understood our users' real pain points early on, versus assuming what their needs are, it could have been much quicker to product-market fit and move faster. – Asad Khan, LambdaTest Inc
13. SAY 'NO' TO DISTRACTIONS EARLY AND OFTEN.
I'd say 'no'—and more often. Chasing every shiny opportunity delayed our clarity. Focus is a superpower, and early-stage distraction is the villain that looks like growth. – Stephanie Harris, PartnerCentric
14. LEARN FROM A MENTOR OR PREVIOUS OWNER.
I would get a mentor, or maybe even shadow someone. If I could, I would buy an existing business and ask the seller to train me. Many mistakes I made the hard way would have been avoided if I had done that. – Al Sefati, Clarity Digital, LLC
15. TEST AND SCALE A DIGITAL-FIRST MODEL.
If I were starting over today, I'd flip the sequence: I'd launch a digital-first playbook and membership built around my frameworks before offering one-on-one retainers. If I tested the templates, workshops, and community perks with a small email list first, I'd iterate faster, build user feedback into my systems, and scale impact and revenue without the slow grind of a traditional agency launch. – Kristin Marquet, Marquet Media, LLC
16. PLAN THE EXIT BEFORE BUILDING THE BUSINESS.
If I could start my business from scratch today, I'd build the exit before the entrance. Instead of obsessing over product-market fit and the competitive landscape, I'd first define who I want to sell to, how I want my days to feel, and the kind of investors, customers, and team I want to work with. Your business should enhance your life, not consume it. – Shayne Fitz-Coy, Sabot Family Companies
17. STICK TO THE ORIGINAL PLAN LONGER.
I would stick to my original business plan, rather than leaning toward revenue. When I counsel other founders today, I commiserate with them about how tempting it is to pivot before they've truly tested product-market fit. I shifted quickly in the early days; had I stuck to my plan, I would have been much further ahead, much faster. Patience and discipline are critical; timing can be managed. – Mack McKelvey, SalientMG
18. PRIORITIZE PROFITABILITY OVER HYPE.
If I could start over, I'd ditch the Silicon Valley playbook. We chased growth and raised early, but not enough attention was paid to profitability. I've learned that lean, revenue-first businesses are stronger, saner, and more sustainable. I'd focus on building something real before scaling it—hype doesn't pay the bills. – Chris Erhardt, Chris Erhardt
19. BUILD A MORE INTEGRATED TECH STACK EARLY.
If I could start from scratch, I'd build a more cohesive tech stack from day one, rather than piecing tools together as we grew. Starting with Google Docs and Sheets was great for low costs, but we've had to create workarounds for systems that don't always play nicely together. We've made it work, but having it work with us as we grew would have saved hundreds of hours of work over the past 15 years. – Travis Schreiber,
