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Coaching for Founder-CEOs Who've Tried Everything | Motherlode Advising

"Everything still lands on my desk."

You've hired. You've delegated. It's still there.

"I hired good people and it's still not working."

You did the right thing. It should have worked.

"We keep solving the same problems."

You're not crazy. And you're not missing something obvious.

"We're profitable but I'm grinding harder than year one."

No one else sees it because the numbers look fine.

"Something's broken and I can't figure out what."

You've tried everything that should have worked.

Let's chat See how I work
Sound familiar? Find out what's actually driving it →

Choose Your Level of Support

Operator-in-Residence: group coaching for founder-CEOs who are solving everything alone

Operator-in-Residence

$500/month

You can't afford a COO and wouldn't know what to hand them anyway. You're tired of solving everything alone — or dumping it on your partner at dinner.

Weekly group sessions with 4 other founder-CEOs. Real problems diagnosed live. Your board of advisors — not a support group.

  • Stop reinventing every wheel
  • Companionship through the hard parts
  • Real advice, not motivational fluff
Yeah, I want in
Strategic coaching for founder-CEOs making high-stakes decisions alone

Strategic Coaching

$1,500/month

The decisions are getting harder, the stakes are getting higher, and you're making them alone. You don't need another hire — you need confidence, momentum, and clarity.

Weekly 1:1 sessions. Your agenda, your priorities. A thinking partner who's been in your seat — not just read about it.

  • High-level direction for the hands that execute
  • Lighten the weight of the hardest calls
  • Complete confidentiality
Let's chat
Leadership team coaching for CEOs whose teams can't align

Leadership Team Coaching

$5,000/month

You hired leaders to take work off your plate. Somehow you're busier than before — and meetings feel aligned until everyone walks out the door.

CEO coaching + team observation + leader 1:1s + strategic facilitation. I see the whole system — not just your view of it.

  • Alignment that survives the meeting
  • Leaders who actually take work off your plate
  • Patterns visible only from outside
I need this

Upcoming Webinars

Coming Soon

Live sessions on the patterns that keep founder-CEOs stuck — and how to break them. Sign up for updates.

Tobey Wyatt - coaching founder-CEOs through the problems no one else seems to get

It shouldn't be this hard.
You're not wrong about that.

I've spent 20+ years inside companies like yours — from scrappy bootstrapped startups to Fortune 50 giants — as CEO, COO, and Chief of Staff. I've been in your seat. I know what it feels like when the fixes don't stick and no one else seems to see the real problem.

I help you find what's actually broken. Then I coach you through fixing it — so it stays fixed.

To the long version

Why Founders Work With Me

Fixes weren't sticking: compass icon representing finding the real problem

Their Fixes Weren't Sticking

They'd tried new hires, new tools, new processes. I help find what's actually broken underneath — so the solution addresses root cause, not surface.

Honoring complexity: stethoscope icon representing real diagnosis

No One Else Seemed to Get the Complexity

I don't simplify your business into a 3-step framework. I help you navigate the real complexity — because that's where the real answers are.

AI-enhanced thinking partner: brain icon representing expanded capacity

They Were Making High-Stakes Decisions Alone

I bring a second brain to the table — supported by AI that surfaces patterns and context a single conversation can't hold. The judgment stays human.

Been in your seat: lighthouse icon representing experienced guidance

They Needed Someone Who's Actually Done This

I've been CEO, COO, and Chief of Staff — from scrappy bootstrapped startups to Fortune 50 giants. I don't coach from theory. I coach from 20+ years of operating at every scale.

What Founders Say

"

Every week, Tobey helps me cut through the chaos and focus on what actually matters. She sees consequences I miss and helps me make decisions that land well across the organization.

Zak
Founder & CEO, Mental Telehealth
"

Tobey helped me see how to make our abstract creative work measurable without losing what makes it special. She translated complex operations into plain English my team could actually use. For the first time, I had clarity on systems I'd been avoiding building.

Elliot
Founder & CEO, Full Service Video Game Audio Agency
"

As my company grew, managing everything from business development to HR became unsustainable. Motherlode helped establish the processes for efficient and sustainable business operations. THIS enabled me to focus on building great software products for our clients.

Keith
Founder & CEO, Boutique Software Development
"

Thank you for all the time and wisdom you've poured into this community. You have made us better in myriad ways – with better processes, improved communications, and a shared sense of mission. You have been a gift not only to our beautiful team as a whole, but to me personally.

Shoshanah
Lead Rabbi, Chicago Synagogue

Free Diagnostic Tool

Not sure what's actually broken?

The Operator Trap Diagnostic maps your symptoms to the pattern keeping you stuck. 10 questions. 3 minutes. No email required.

Take the Diagnostic

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Book 30 Minutes

No pitch, no pressure. Tell me what's going on and we'll figure out if I can help.

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Not ready to talk yet? Drop me a message and I'll respond within 48 hours.

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