
When I started Wainger Group 25 years ago, I had a desk, a phone, a big idea, and no clue what was ahead. What I did have was a deep curiosity, a passion for storytelling, and a belief that communications done right can change everything. A quarter century later, I’ve learned that running a business is equal parts strategy and serendipity, grit and grace. Along the way, I’ve worked with inspiring clients, navigated tough calls, celebrated wins, and yes, made my share of mistakes. To mark this milestone, I’m sharing 25 lessons, hard-earned truths, practical advice, and a few “wish I’d known that sooner” moments that have helped me build a resilient, values-driven business. Whether you’re just starting out or decades in, I hope these spark insight, maybe a laugh, and most of all, encouragement.
1. Know When to Let Go
Whether it’s a contractor, a project, or even a lucrative client, holding on too long can cost more than it’s worth. Trust your gut when performance drops or values clash and move on gracefully.
2. Diversify or Die (Metaphorically)
Don’t rely on one industry or client type. Spread your work across sectors to stay resilient when markets shift—and uncover unexpected synergies.
3. Make Curiosity Your Superpower
You don’t need an MBA to succeed—just an insatiable appetite to learn. Dive deep into your clients’ worlds, speak their language, and show them you care by truly understanding what drives them.
4. Leave People Laughing (and the Door Open)
End every relationship on a high note, even the tough ones. You never know where people will turn up again, and a gracious exit can be your ticket to future opportunities.
5. Go For It
Don’t wait for perfect clarity or a flawless plan—take the leap. Growth comes from movement, not hesitation.
6. Don’t Go It Alone
Success is never solo. Surround yourself with smart, supportive people who challenge and guide you.
7. Stay True To Who You Are
Growth doesn’t have to mean getting bigger. Stay true to the life and business you actually want, not the one others expect.
8. Put Clients First, Not Your Process
Tailor your work to each client’s needs, not your comfort zone. Flexibility builds trust—and long-term relationships.
9. Know When to Walk Away
Whether it’s a contractor or a client, if it’s not working, let it go. Protect your time, values, and sanity.
10. Diversify to Thrive
Avoid relying on one industry or client type. A broad base not only offers security but sparks unexpected opportunities.
11. Let Curiosity Lead
A hunger to learn can take you further than any degree. Ask questions, dig deep into your clients’ worlds, and stay genuinely interested—it’s the best way to build trust and grow expertise.
12. Exit Every Relationship with Grace
Always leave things on a high note, even when it’s hard. You never know when paths will cross again, and a kind, professional exit can open unexpected doors.
These first ten lessons are just a glimpse into the insights I’ve gathered over 25 years in business. From leaping to knowing when to let go, they reflect the everyday realities, tough choices, and rewarding moments that come with building something meaningful. Whether you’re leading a company, launching a venture, or navigating your next chapter, I hope these takeaways offer perspective and encouragement.
Stay tuned for more lessons in Part 2, because the learning never stops.