Motherlode Advising LLC, Chicago IL

Tobey Wyatt

Motherlode Advising LLC

About Us

You built something that works. So why does it still need you for everything?

Your P&L is solid. Your team is growing. But somehow you're working harder than year one — and the fixes you've tried keep breaking six months later. New hires, better tools, tighter processes — they help for a while, then the same problems come back.

That's not bad execution. That's a diagnostic problem. You're solving symptoms, not root causes. And you can't see that from inside.

I help founder-CEOs of 5-75-person companies find what's actually broken—not just what's on fire today. I don't give you a playbook and walk away. I coach you through the diagnosis so you understand the pattern, not just the fix.

20+ years from scrappy bootstrapped startups to Fortune 50 giants. I've been in your seat. I know the difference between a system that's actually failing and a founder who just needs someone to help them see what they're too close to see.

I don't execute for you. I don't build your systems. I build your capacity to think like the CEO your business needs — so your next hire, your next fix, your next decision actually sticks.

If you've tried multiple fixes and none of them stuck, let's talk.

How We Got Started

I launched Motherlode after 20+ years as "the operator behind the visionary" — from scrappy bootstrapped startups to Fortune 50 giants, making big ideas actually work.

The pattern I kept seeing: brilliant founders building amazing businesses, then getting trapped by operational complexity. New software, new processes, new hires... and six months later, everything breaks again. Not because they weren't capable, but because they were treating symptoms instead of root causes.

Founders didn't need another implementer. They needed coaching to think differently. To see patterns they were too close to see. To develop thinking that identifies what's actually broken, not just what's loudest.

That's why Motherlode exists: coaching founder-CEOs from operational firefighting to strategic leadership. I don't build your systems — I build your capacity to think about them differently.

Networking Events
Friday Mar 20th 1pm-2:30pm CDT
Napkin Networking: Chicago with Motherlode Advising LLC
The best business ideas start on napkins. So do the best connections. Napkin Networks is in-person networking that actually works - no awkwar...
Friday Apr 10th 9am-10am CDT
Loop'd In: Chicago Networking with Motherlode Advising LLC
Tired of Zoom networking that feels like watching paint dry? Loop'd In is different. Virtual networking for Chicago business owners who actually ...
Friday Apr 24th 9am-10am CDT
Loop'd In: Chicago Networking with Motherlode Advising LLC
Tired of Zoom networking that feels like watching paint dry? Loop'd In is different. Virtual networking for Chicago business owners who actually ...
Products & Services
1:1 STRATEGIC COACHING ($1,500/month) by Motherlode Advising LLC
Description: Every decision lands on your desk alone. Your team can't understand the weight you carry. Venting to your board feels dangerous. You...
Operator-in-Residence ($500/month) by Motherlode Advising LLC
Lonely at the top. No one gets it. You're burning out. Most CEO groups are either expensive country clubs or cheerleading circles. This is neithe...
Motherlode Office Hours (4 session pack for $100) by Motherlode Advising LLC
You're curious about coaching but cautious about the cost. You want to test the fit before committing thousands. You need help now, but can't commi...
Recommendations Given (1)
"Rosalie is such a pleasure to work with! She can translate ideas into actionable plans and..." Read more "Rosalie is such a pleasure to work with! She can translate ideas into actionable plans and marketing materials, and is able to listen and pull out the key information and takeaways while a visionary type brainstorms (not everyone can do that!). ePIC is doing some amazing things to benefit consumers in the estate planning space, as well as agents in the financial and insurance spaces, to improve their own sales, marketing, and product offerings."

Our Recognition

We're highly recommended by locals on Alignable

Highly Recommended

By 25+ Local Business Owners!

Team

Founder / CEO Advisor