Getting Started in Small Business: Lessons from a Serial Entrepreneur
Entrepreneurs are built differently. We feel a passion, a calling, to realize our dreams and take risks to make them happen. We want the sense of accomplishment that comes from building it ourselves and reaping the rewards.
After building three successful SaaS startups, I’ve learned important lessons that transcend industries and sectors. Whether you’re offering products or services, here are some tips to grow your business, make more money, and become a better leader.
Know Your Customer Inside and Out
One of the most important lessons I’ve learned is that a deep understanding of your customer is the cornerstone of success. You may think you know what your audience wants, but it’s not until you listen to their pain points, goals, and aspirations that you can create solutions that really offer real value.
Make sure you engage with your customers regularly. Whether you offer products in a small boutique or you’re a service provider, the customer is still king. Gather feedback through surveys, social media, or face-to-face interactions to better understand your customers' needs and deliver value to them. Use that feedback to choose “tester” customers and develop a minimum viable product or desirable offerings that better fit the audience.
Focus on Solving Problems
Each of my startups succeeded because they addressed specific, pressing problems for the target audience. Solving a real problem creates value, and customers are willing to pay for that.
Evaluate your offerings. Are you solving a genuine problem for your audience, or is your product or service something that’s “nice to have?” Focusing on high-impact problems can justify premium pricing and ensure customer loyalty — especially if the market doesn’t offer a suitable solution.
Leverage Data to Drive Decisions
With SaaS like community management software, metrics like customer acquisition cost (CAC) and lifetime value (LTV) are crucial to ensure that you’re on the right track. In a small business, the metrics may differ, but the principle stays the same: use data to inform your strategies, rather than your assumptions. While your gut instinct can get you far, it should be combined with data to get better results that are grounded in evidence.
Identify your key performance indicators (KPIs) based on your goals for your business. Track them consistently to uncover trends and areas for improvement. Whether it’s website traffic, customer retention, or sales conversions, data-driven insights can guide smarter investments in marketing and sales.
Build the Right Team
No business succeeds without the right team at the helm. Early in the startup world, I realized that hiring for skill alone wasn’t enough. Cultural fit, alignment with company values, and adaptability were equally important. A cohesive team can weather the challenges that are inevitable in business and innovate to overcome them.
Quality candidates have plenty of options, including attractive compensation packages at established, well-known companies. They choose to work for a small business because they want to play a role in building it from the ground up and seeing how their work contributes to success. Invest in your team’s growth and create an environment where they feel valued. Whether you’re hiring your first employee or expanding an existing team, prioritize people who share your vision and are eager to grow with you.
Embrace Experimentation
Success rarely happens on the first try. My startup success came with pivots and changes that were necessary before they found their stride. Experimentation and learning through trial and error is a natural part of building a business.
Don’t fear change, especially as an entrepreneur. You have to get used to it. If something isn’t working, be ready to adapt — even if you’re attached to your idea and feel passionately about it. Test small changes to your products, services, and marketing campaigns, learning from the results. Flexibility can lead to breakthroughs you never thought possible.
Prioritize Marketing and Sales
For many small business owners, marketing can feel overwhelming, or even unnecessary. But without it, your offerings may seem invisible. One of the most important lessons I learned is that even the best product or service won’t sell itself. Effective marketing and sales strategies are essential to attracting customers.
Allocate time and resources to your marketing efforts. This may mean refining your social media presence, investing in local advertising, or building your email list. Remember, consistency is key.
Learn to Say “No”
One of the toughest lessons was learning to say “no.” Entrepreneurs are wired to seize opportunities, even if that means spreading yourself too thin. But in doing so, you risk making mistakes and reducing your impact.
Set clear priorities and stick to them. Always evaluate new opportunities and consider whether they contribute to your goals. If they don’t align, don’t be afraid to decline them and focus your energy on the activities that serve you. Outsourcing some of the work, such as bookkeeping or marketing, can help you free your time to focus on your goals.
Invest in Yourself as a Leader
Leadership is a skill that requires learning and refinement. Many leaders underestimate the importance of emotional intelligence, communication, and delegation, but your ability to lead directly influences your team’s performance and morale — and your business’s success.
Commit to your personal and professional growth. Seek mentorship, read books about leadership, attend workshops, or take short courses to develop your leadership skills and important soft skills. Becoming a better leader is an incredible long-term investment.
Plan for the Long Game
It’s easy to get caught up in the quick wins, but sustainable growth requires a long-term perspective. For me, this is about balancing immediate revenue goals with investments in innovation, relationships, and brand equity that serve the long-term goals.
Develop a strategic plan that accounts for both short- and long-term objectives. Revisit it regularly to ensure you’re on track and adjust as needed. Growth is a marathon, not a sprint.
Don’t Put Your Idea Off Any Longer
Building a business is an incredible journey. Whether you’re opening a consulting firm, launching an e-commerce business, or running your own local artisan shop, the principles of understanding your customers, solving real problems, leveraging data, and investing in leadership apply. Embrace the challenges and celebrate the wins.
About the Author:
Michael Bollinger, a Lexington, Kentucky-based entrepreneur, has left a lasting mark on the tech and software landscape. As the founder of LegFi and File990, Michael launched PayHOA.com in 2018 after Togetherwork acquired his first two ventures.
PayHOA is an affordable community management software for homeowner associations that streamlines payments, communication, and vendor management. Beyond his entrepreneurial pursuits, Michael finds fulfillment as a devoted husband and a loving father to his three children.