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Financial guidance through the entrepreneurial wilderness

We steady financial uncertainty through strong foundations and strategy so you can grow a durable, lasting business.

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The world needs business owners like you

Running a small business or startup can often feel like navigating uncharted territory. With so many unknowns, competing priorities, and financial information coming from every direction, it is easy to lose your sense of direction.

 

Whether it's regular check-ins, short-term projects, or ongoing support, we offer clear and practical financial guidance shaped around your unique path. We help you find clarity, make confident decisions, and keep moving forward with purpose.

Problems We Solve

Managing your books is a pain and you're not getting enough from the reports

Clean books are important, but the real value is in being able to understand what the numbers are really telling you about your present and future business health. We'll help you with all of it, so you can use that information to make confident and informed decisions.

You don't have anyone to help you workshop ideas or keep you accountable

Sounding Board Sessions are one-hour meetings where you can bring questions, workshop ideas, or get feedback on something you're stuck on. Whether it's financial, strategic, or operational, this provides an experienced and objective perspective.

You feel like your business is off track and you can’t seem to get a handle on it

Reset and Refresh is built for business owners struggling to understand why their business finances aren’t working and need a clear, grounded plan to get back on track. We dig into the numbers, identify the problem areas, and develop a workable and achievable path forward.

You have a new business and need help starting out on the right foot

Launch Pad helps new and early-stage business owners set up their finances with confidence, clarity, and strategy. We establish the right systems and foundations from the beginning so you can focus on what you do best without falling into the traps that derail so many small businesses.

Success Stories

Deepwoods Financial Tree

"Jake has been my guy for over 10 years. Early on, he helped me to set realistic goals for myself when I desperately needed guidance. I’m proud to say that I’ve been able to reach many of those goals by taking his advice. He has helped me to better understand things about my business that I simply never learned elsewhere. I’m very grateful to have Jake lookin’ out."

Tyler - Musician/Producer

Deepwoods Financial Tree

"Jake came on about a month after we opened and I can't overstate the difference it made. In our second meeting, he found thousands of dollars we didn't even realize we hadn't been paid. Restaurants move so quickly and having Jake in the background to help us stay on track and improve has really been such a wonderful partnership."

Michael - Restauranteur

Deepwoods Financial Tree

"We were in a pretty terrible spot and not really admitting it to ourselves. I reached out to a friend who recommended we talk to Jake. I had low expectations, because we hadn't had great luck with other people in the past. Well...that was three years ago. We're still in business and Jake is still on my calendar every month."

Justin - Operations Director

Deepwoods Financial Tree

"We had been working on and talking about our idea for about 5 years, but all on the product and design side. When we finally decided to pursue it, it hit us immediately that we really didn't know how to startJake took us through the first six months pretty much step by step. He took away a lot of the uncertainty that we were feeling at the time by helping us get organized and prepared."

James - Startup Founder

About

My name is Jake Dougher.

For nearly 20 years, I've worked with business owners helping to navigate risk, ensuring financial stability, and building strong, resilient businesses. 

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I spent years in music business management before receiving a Master's Degree in Business with a focus in corporate sustainability. 

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After graduate school, I spent 3 years as CFO for an environmentally-driven startup focused on improving water usage efficiency. 

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My work now is with dedicated business owners working hard to build profitable and impactful businesses.​ Everything I do is anchored in the guiding principal that this is your life's work. My job is to help you get the most out of it. It's that simple.​

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I'd love to answer any questions you might have and learn more about you and what you're working on.

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Get in Touch

PO Box 1593

Petersburg, AK 99833

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