Running a business solo is like navigating a cross-country trip with no map and no co-pilot. The Headway Advisory Group gives small business owners the seasoned, practical guidance that big companies take for granted — without the corporate overhead.
“Most small business owners have no board of directors, no trusted advisor group, and no one to call when a hard decision hits at 10 PM. They’re making it up as they go — and paying the price for it later.”
— Doug Thorpe, ICF ACC | Executive Coach | 5x Entrepreneur
SOUND FAMILIAR?
Owning a small business is one of the most rewarding things a person can do. It’s also one of the loneliest — especially when the weight of every decision falls on you.
Cash flow, pricing, projections — you’re making calls that could sink or save the business, often without a finance background or trusted sounding board to test your thinking.
You hired good people. But developing them, holding them accountable, and building a culture where they actually want to stay? That’s a different skill set than running the business.
You’ve hit a plateau and you’re not sure why. More effort isn’t producing more results. Something in the operations, the offer, or the leadership needs to change — but what?
Employees look to you for answers. So does the bank. Without a trusted outside perspective, it’s hard to know if you’re making bold moves or just expensive mistakes.
Whether you’re buying a business, planning an exit, or passing things to the next generation — ownership transitions are among the most complex, emotional, and high-stakes things you’ll face.
You didn’t start this business to feel exhausted and isolated. But somewhere between the dream and the day-to-day, it got heavy. You need a system — not more hustle.
Think of a Fortune 500 CEO. They don’t make major decisions alone. They have a board of directors, a leadership team, and advisors they trust deeply. The Headway Advisory Group gives small business owners that same kind of reliable, experienced guidance — a real team in your corner, working alongside you through the day-to-day and the high-stakes decisions alike.
We help you understand your numbers — not just read them. Cash management, business plans, financial projections, and preparing for funding or growth. Because smart ownership starts with knowing where you actually stand.
Process mapping, project planning, and sustainable profit margin — we help you build a business that runs reliably, scales without chaos, and doesn’t require you to be everywhere at once.
Great teams don’t just happen. We work with you to develop the people under you, build accountability systems, and shift from managing tasks to multiplying talent. That’s the real unlock for any growing business.
Buying a business, planning your exit, or passing the torch? These moments matter. We bring decades of M&A, integration, and succession experience to help you navigate the process — and the emotions — with clarity and confidence.
The best ones don’t just answer your questions — they ask you the questions you haven’t thought to ask yourself yet. That’s what we do. We bring a clear-eyed, outside perspective to your business, challenge your blind spots with respect, and help you see around the corners that are hard to see from inside.
A no-pressure 30-minute conversation about where you are, where you want to go, and whether the Advisory Group is the right fit. We're not for everyone — and that's intentional.
Pick the level of access that makes sense for your stage and goals. All plans are month-to-month — no long-term contracts, no fine print. You're here because it's working, not because you're stuck.
You set the agenda. Bring real challenges, real decisions, and real questions. We show up prepared, engaged, and focused on your specific situation — not a generic playbook.
Our monthly peer advisory group puts you in the room with other small business owners who get it. Real conversations, real accountability, real progress — together.
There’s something powerful that happens when small business owners sit in a room together — even a virtual one. The Headway Huddle is our monthly peer group where owners bring their real challenges, get honest feedback, and walk away with clarity they couldn’t find alone.
Think of it like a trusted mastermind — minus the hype, plus the practical common sense you actually need to move forward.
Consultants hand you a report and leave. We stay in the boat with you. Our advisors have founded companies, run operations, navigated M&A, and led teams — so when they guide you, it comes from real experience, not a textbook.
"I cannot express how thankful I am for the conversations and guidance over the past 6 months. You have helped me set a straight course for who I want to be as a leader — and that is something I may never have gotten without you."
"Doug epitomizes a great leader — a servant leader. He is humble and willing to share his experiences to help others reach their potential. Doug empowers everyone he works with. So fortunate to have had the opportunity."
"I learned so much about my leadership style — but more importantly, how to take it to the next level. Even after our sessions ended, Doug continued to check in. He helps you understand the psychology behind your style and how to improve."
Here’s the truth about advisory work: it’s only valuable if the advisor has actually been where you’re going.
Doug has founded five companies, led banking teams for 20 years, served as a U.S. Army officer, and coached more than 1,500 leaders across 19 industries. He’s not advising from a theory — he’s speaking from the same room you’re standing in.
His approach is simple: common sense over complexity. He helps business owners cut through the noise, see their situation clearly, and take practical steps forward — without the corporate jargon or the ivory tower advice.
1,500+ Leaders coached across every level of business
19 Industries served — from banking to manufacturing to healthcare
20 Years – Senior banking executive and M&A experience
5X – Entrepreneur who has built, scaled, and exited companies
3 Years – Culture transformation at Fortune 500 scale (ExxonMobil)
The Headway Huddle is a monthly peer advisory group for small business owners. Real conversations. Real challenges. Real progress — together.
A free 30-minute intro call is all it takes to find out if the Headway Advisory Group is the right fit. No pitch, no pressure — just an honest conversation about your business and what you’re trying to build.
Or reach us directly at 24 Greenway Plaza, Suite 1800 · Houston, Texas 77046
