Coaching you through what's next.

Choosing your own path doesn't mean walking it alone.

Jake Wolpert

Who I work with

Two situations. Same thing underneath: you're ready for what's next, and you want a plan, not a pep talk.

Ready to make the leap

You're successful, but restless.

Good job. Decent money. And Sunday nights feel heavy. You keep landing on the same question: is this it for the next twenty years?

I help you build the exit strategy while you're still employed. No reckless quitting. Systematic planning that turns "someday" into a real timeline.

Out on your own, and it's hard

You're building it solo, and no one warned you how heavy that gets.

Whether you just launched or you're starting to gain real traction, it's all on you. Every decision, every priority, every high-stakes call with no playbook and no one to think it through with.

I help you get out of your own head: what to focus on, what to let go, and how to make the big calls with someone in your corner who's seen it before.

If you've caught yourself thinking one of these, we should talk.

You don't need a total life overhaul. You need a clear head, an honest second opinion, and a plan you'll actually follow.

"I know I want out. I just don't have a plan."The ready-to-leap
"I wish I was less scattered."The scattered builder
"This is taking off faster than I'm ready for."The early-success founder
"I don't need someone to do it for me. I need someone to think it through with."The one who wants a partner

How I coach

The ETHIC Method.

Breakthroughs aren't luck. They come from the right environment. ETHIC is the five things I make sure are true in every conversation. They're the difference between feeling good for an hour and changing what you do on Monday.

E

Empowered

You leave feeling confident and in control of your transition, not reactive to circumstances. The point is movement, not reflection for its own sake.

T

Taught

You gain frameworks for thinking intentionally that stick with you long after our work ends. Practical tools, not theory.

H

Heard

Your specific situation, values, and aspirations get fully understood and honored. Most high-performers don't have anyone who really listens without an agenda.

I

Inspired

You move past limiting beliefs and connect to a bigger vision of what's possible. Not hype. Genuine possibility you hadn't considered.

C

Challenged

I push you past safe thinking and name the limiting beliefs you've stopped questioning. You're hiring me to help you think bigger, not to be agreed with.

I ask more questions than I give answers. When you say it out loud yourself, it sticks.

In their words

Don't take my word for it.

"
I've worked with Jake across multiple companies over nearly a decade. From pricing to negotiation to growth strategy, he turns my messy thoughts into obvious decisions. His coaching has accelerated my growth as I've gone from W2 employment to running my own business, and I wouldn't want to do it any other way.
Ryan BurgessFounder, Iceburged
"
Working with Jake has been one of the best investments I've made in building my business. He has saved me months of trial and error by helping me avoid costly mistakes, think through challenges, and make better decisions faster. I genuinely would not have been able to build PClub Talent as quickly without his guidance. Beyond that, he's been an incredible resource and someone I truly enjoy working with.
Lauren SzuchanFounder, PClub Talent
"
Working with Jake is an absolute pleasure. He helped me set up my business and build the habits that grow it, but what sets him apart is that he never loses sight of the life around the work. He reframes whatever I'm wrestling with so the right decision gets clearer, and keeps my own enjoyment and family life at the center of it. He gives sage advice, listens well, and challenges in the right way.
Matt CoxFounder, Matt Cox Consulting

Working together

Two ways in. Both start with a conversation.

One strong conversation

The Working Session

For when there's one real decision or fork in front of you, and you need to think it all the way through with someone who'll push.

  • One focused 45-minute session
  • Built around one decision, idea, or stuck point
  • A recap email capturing what we decided and your next moves
  • Pre-work so we go deep from the first minute

$450

A real arc of change

The Coaching Program

For navigating a full transition, whether that's the leap out or the rebuild of how your business runs, with structure and accountability the whole way.

  • Four 75-minute sessions
  • A tailored plan, and the frameworks to keep running it
  • Accountability between sessions, not just during
  • Written recaps that keep the work alive between sessions

$2,000

Not sure which fits? That's what the first call is for.

Book an intro call
Jake coaching his son on the pitching mound

I've been doing this for years. I just didn't call it coaching.

For most of my career, I was the person colleagues, founders, and friends came to when they were stuck at a real crossroads. A job decision, a business that had stopped working the way they built it, the question of whether to leap. I'd help them cut through the noise and find the move that was actually theirs to make.

Eventually I realized that that was the work. Not the title on the org chart. It was the part where I help someone remove the belief that's holding them in place and see the bigger version of what's possible.

My approach is direct and practical. No vision boards. No "find your passion" sessions. Just honest conversation, frameworks that work in the real world, and someone in your corner who'll tell you the truth and hold you to the plan.

I run a sales consulting practice too, which keeps me close to how real businesses actually grow. But this, coaching people through what's next, is the work I believe I was put here to do.

Let's talk about what's next.

An intro call to talk through what's pulling you toward a change, what feels stuck, and whether working together makes sense. No pressure, just a real conversation.

Book an intro call

Usually 30 minutes. No prep needed.