This Guy Helps People Escape Golden Handcuffs

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Zach Ashburn didn’t set out to be the Golden Handcuff Guy. But after years of helping tech execs and employees exit the W2 life, he and his partner realized that’s exactly what they should lean into.

Zach runs Reach Strategic Wealth, a tax and investment planning firm built for people on the edge of leaving their W2. His clients are the real deal. Operators, consultants, and tech leaders pulling the ripcord and asking, “What’s next?”

I sat down with Zach to learn more about how he’s building the go-to firm for corporate exit planning.

1. Who are you and what do you do?

I’m Zach Ashburn, co-founder of Reach Strategic Wealth. We do corporate exit planning for executives or employees looking to escape their golden handcuffs.

2. What’s your backstory and how did you get here?

I started in banking, then moved into traditional wealth management, the "give me your money and trust me" world. My co-founder Mike Kelly and I each started our own firms, but we noticed a pattern. His tech clients with equity packages were starting to explore consulting. My consulting clients were starting to receive offers with equity.

That life cycle clicked for us. We merged our firms and built a planning-first practice focused on that inflection point: The moment someone decides to leave corporate.

3. How did you get your first customer?

The classic unscalable way: personal network. We made a list of who might pay us or advocate for us, and just told them what we were doing. Five years later, we still revisit that list and refresh it with updated messaging.

4. What’s worked best to attract and retain clients?

Social media has brought us some of our best clients, especially when we share real stories (carefully scrubbed, of course). It’s made us better storytellers. But the most consistent source is person-to-person networking, especially for high-trust, high-ticket services.

Retention comes from one thing: solving recurring pain points. For our clients, that’s tax planning. As they grow or shift into new life stages, we want to be the ones helping them stay proactive and prepared.

We’ve also built strategic partnerships, like a health insurance concierge and care journey guides, because leaving corporate usually comes with more than just financial questions. We want to be there for all of it.

5. How’s the business doing today, and what’s next?

Right now, we’re deep in a top-of-funnel push. We’ve said it out loud: we want to be known as “the golden handcuff guys”. That’s our brand.

To get there, we’re narrowing in on LinkedIn as our hub. We’re pulling back from other platforms and using this next 90-day sprint to focus on positioning.

Operationally, things are dialed in. We’ve got strong systems, good division of labor, and are starting to delegate more outside our core skill sets. It’s growth mode, but with growing pains.

6. Was there ever a moment you thought it wasn’t going to work?

Honestly? Every day. That’s just part of the game.

The danger isn’t failure, it’s mediocrity. You can coast in this industry if you want to. But that’s not what we’re here for.

Every six months, we have a wake-up moment. We see where we slipped, what we dropped, and recommit. That’s the work. You have to stare at the problem longer than anyone else. Eventually, the problem blinks.

7. What do outsiders not understand about your industry?

Most people think financial planning means managing assets or selling a product. We’re doing something totally different: tax planning, coordinating, and guiding people through big life transitions.

But it’s hard to communicate that when everyone has already slotted you into a mental box. So we simplify: “We’re like the firm you’re familiar with, plus tax planning.” It’s not the whole picture, but it opens the door.

8. Favorite tools?

We intentionally keep our stack lean. Google Suite runs ops. We use industry-specific software for planning, portfolio management, and tax work. And we recently added Zocks, an AI meeting assistant that integrates with our CRM. It handles notes, follow-ups, and emails, basically replacing a full-time admin.

9. Most influential books or content?

Essentialism has been big for us. So has The E-Myth, especially at this stage of transitioning from practitioner to operator. Other favorites: Nathan Barry’s podcast for creator stories, Chris Koerner’s show for shiny object indulgence, and 10x Is Easier Than 2x for shifting how we think about growth.

10. If you had to start a new business today, what would it be?

I’d build a local service for aging in place. Smart home tech, security systems, tech support, maybe even quarterly air filter swaps. There’s so much opportunity to serve older folks who want to live independently longer. The tech exists. They just need help using it.

Also, my kids would actually be able to see what I do. That’s something I think about a lot.

11. Best advice for other entrepreneurs?

Everything works if you do it well and consistently. Pick a channel. Show up. Do the basics. It’s more than hard enough, and more than good enough.

Final Takeaways

1. Your next business might be hiding in your clients’ life cycles. That’s how Zach found his.

2. High-trust, high-ticket services are still won through referrals and reputation.

3. Social posts don’t need to go viral to work. Just be consistent.

4. Tax planning isn’t sexy, but it’s necessary and valuable.

5. You don’t need to do everything. Bring in partners to cover what your clients really need.