Shelly Oswald, business and high performance coach

I learned to be a small business CEO the hard way ... so you don't have to.

SHELLY OSWALD  ·  35+ YEARS AS A BUSINESS OWNER

Certified High Performance Coach  ·  Pumpkin Plan Business Growth Strategist  ·  Fix This Next Advisor  ·  QuickBooks Online ProAdvisor

My Journey

A degree in accounting and growing up in a family of entrepreneurs didn't prepare me to step into the CEO role for a small business. You know, the one where I have to set the vision, manage the growth, and run the high-level strategy while still doing the hands-on daily work.

I learned by making expensive and painful mistakes ... today I share my experiences so the growing is less painful for the women I work with.

After getting my accounting degree, the real start came when I systematized and turned my husband's cash flow challenged plumbing company into a thriving operation.

Then my dad, CEO of my great-grandma Ruth's business, a John Deere dealership and school bus business, got cancer. I stepped in to help. When he died, I became CEO of a struggling business I barely knew, with 30 grieving employees who had just lost him too.

Not long after, my husband and I bought Granny's business outright... after the bank decided a woman who was in her 90's was too old to guarantee 6-figure loans every year.

It was hard for several years. There was no playbook and nobody to call, and I remember the ugly cries behind closed doors when none of what I knew told me what to do next.

But I handled it. I ran that business for 17 years and led it through 9/11 and the 2008 recession, and we came out the other side stronger.

7+ figure revenue every year. 30 amazing employees. Bills paid and payroll met every week.

And a life. Boats and boating every weekend in the summer. Snowmobiles in the winter. Time off to care for ill relatives. I did the work, but I played and had a good life too.

Then in 2010 we sold it, and my job went with it. I started the farm... 113 acres and a herd of grass-fed cattle, from scratch.

And I did what all the "experts" told me to do. More products. More markets. More everything. I ended up at seven farmers markets a week, six figures, no life and no profit. I was pulling every lever I had and none of them worked.

The harder I worked, the harder it got to manage the business, and my nice life and free time disappeared.

I knew what a business supporting a life looked like. I knew it was hard work to get there. And I couldn't figure out why the farm wasn't getting there.

Chaos had taken over.
And I wasn't able to work my way out of it this time.

Looking back, I'd started the farm business just to start a business... because I enjoyed the challenge of being a business owner. Then, I expected it to support my life like the businesses before it.

The problem was I didn't design the business to work for me. In that season of change, I had no vision of what I wanted my life to look like let alone the business would support that vision.

The way out started with getting clear on where I wanted to go and true clarity about my cash-flow numbers.

I carefully let go of the clients and offers that drained me so I could focus on the ones I loved and that made money. I built the structure to serve them better and found a rhythm that made it stick.

Seven farmers markets a week slowly became one delivery a month. Eight to ten hours a day became about an hour a week. Today, I sell to customers I enjoy, and I raise food in a way that I'm proud of.

Here's the part I didn't understand at the time. I'd done this before... in my husband's plumbing company, at the dealership. I knew what a business supporting my life looked like and was able to get two businesses there. I just didn't know what I did that worked. So I went on a search.

That's when I met the work of Mike Michalowicz and discovered Profit First and the Pumpkin Plan and immediately saw the missing piece ... I added complexity when growing the farm when simplifying and removing complexity was what I did in the past. It wasn't about doing more, it was about doing less.

I got certified in Profit First, the Pumpkin Plan, and Fix This Next, and trained with Brendon Burchard in High Performance Coaching for more personal growth.

Years later, the farm season is winding down for me. I'm getting older, and what I want my life to look like has changed. So the business is changing with it - again.

After 35+ years and more than a few hard business seasons of my own, I've decided to use what I've learned to help overwhelmed women business owners do the same - without the pain. 

What I Believe

Integrity is non-negotiable.

  • Speak the truth and assume best intent.
  • Do the right thing even when no one is looking.

We're stronger together.

  • Show up and make a difference.
  • You don't have to figure this out alone.

Mindset matters... but it's not enough.

  • Shit happens ... grow from it, build character, and be grateful for the lesson.

Courage is a practice.

  • Call out injustice when you see it.
  • Be a voice for purposeful change, in your business and your life.

Empower rather than enable.

  • Trust people enough to be truthful and don't just tell them what you think they want to hear.
  • Help others to build the skills and confidence to do it themselves.

What I Talk About

Around here, I help you ditch the chaos and build the brain space and financial stability to run a business that actually supports your life.

Expect real talk on:

Financial Intimacy Building a close, fearless relationship with your numbers, showing up to them regularly, without dread, as a normal part of running your business.

Smart Systems Documented processes and simple systems that make serving your customers and running your business easier, not harder.

Anti-Hustle Life First Building a business that supports your life instead of draining it.

High Performance Protecting the person running the business, with the daily, monthly, and quarterly rhythms that make the systems actually stick.

The Highlights

✓ 35+ years owning and running profitable businesses

✓ 17 years running a 7-figure dealership and school bus operation

✓ Built a 113-acre direct-to-consumer grass-fed beef farm operation from the ground up

✓ Certified High Performance Coach

✓ Pumpkin Plan Business Growth Strategist

✓ Fix This Next Advisor

✓ Accountant by degree. QuickBooks Online ProAdvisor

I've been lost in the weeds and found my way out, more than once. I'll save you the degree, the decades, the dollars, and the drowning.

If you've been carrying the weight of your business alone, you don't have to anymore.

Work with me →