Beyond the Playbook: Day 1 Takeaways from My First OEI Experience

Yesterday was my first day at the Okoboji Entrepreneurial Institute, and while I was surprised to be asked to join, once I sat down and talked with the students, I knew exactly why I belonged at that coaching table.

OEI Thank You

Not because I'm the smartest marketer in the room or the most talented business owner in northwest Iowa. I'm there because someone I've built trust with over years of showing up, delivering results, and being transparent about both my wins and my struggles picked up the phone and asked me to join this week.

That matters more than any credential on my wall.

As one of the speed coaching volunteers working with 31 college students from universities across Iowa, I wanted these future entrepreneurs to see something specific: a woman who was born on a US Air Base abroad to an immigrant mother and an American father, who survived a childhood that could have derailed everything, but who built a business and earned a seat at tables like this through connections, follow-through, and refusing to let anyone else's opinion define what was possible.

Because here's what I learned in session after session yesterday: The students who made me stop mid-conversation and lean in weren't necessarily the ones with the most polished presentations or detailed market research. They were the ones brave enough to share what actually mattered to them.

My Coaching Approach: Beyond the Data Points

Here's how I approached every conversation yesterday, and honestly, how I work with all my clients:

Differentiate through your authentic story. Listen to your gut, not just your analytics. Write down what success looks like in 2-5 years and work backwards from there. Then write down your challenges and goals, and hold yourself accountable to your own path.

Any marketing agency can tell you to do X, Y, and Z and give you data to prove it works.

But what we know about marketing - what really moves people - is that sometimes the most powerful strategies are rooted in gut instinct, authentic connection, and the courage to follow through on what matters to you, even when it doesn't fit the standard playbook.

It's about aligning with people who can be vulnerable with you, and you with them.

Because that's where real business relationships are built.

The Commodity Trap

Think of differentiation like a crowded farmers market. Every vendor has fresh produce. Every booth claims to be organic, local and sustainable. The technical quality might be nearly identical across the board. So what makes you stop at one stand instead of walking past ten others selling the same tomatoes?

It's never just about the tomatoes.

I met a flower farmer yesterday whose grandfather started the family business generations ago. I bet he could talk about soil composition and seasonal growing cycles with the best of them. But what made me stop and really listen wasn't his technical expertise - it was his vision to disrupt an entire industry by building on the foundation his grandfather laid while creating something entirely new. His grandfather didn't just sell the plants back then - he also helped develop potting systems that eliminated the need to tear apart root systems when transplanting, solving a problem that gardeners didn't even know they had at the time. So the "root" (pun intended!) of the business was selling plants to other businesses, but the heart was with his innovative grandfather - and why I think this business has seen long-term success.

Today, the family business serves companies like Hy-Vee and Bomgaars, but this next generation isn't content with maintaining the status quo. He wants to take his grandfather's same innovative spirit further, creating new solutions that make gardening easier for everyone.

He sat down at my table looking for marketing and scaling advice - the tactical stuff most coaches would dive right into. Instead, I found myself telling him to slow down and work on telling his grandfather's story, making it real for himself, and listening to his own gut about where he wants to navigate the next iteration of the family business.

Because here's the thing: When you can authentically connect your grandfather's legacy of innovation to your vision for the future, the marketing tactics become secondary.

Your story becomes the strategy.

That conversation reminded me that the best stories aren't just about where you came from; they're about where that foundation is taking you. They're the thing that transforms a commodity into something irreplaceable.

Your Gut Knows Before Your Spreadsheet Does

I watched these students present market analyses that would make MBA professors proud. Detailed competitor research, demographic breakdowns, growth projections - all the "right" stuff. But when I asked them why they cared about their particular solution, why it mattered to them personally, that's when the magic happened.

That's when their voices changed. Their posture shifted. They stopped reciting and started believing.

Your gut has been processing information longer than any business book has existed. It's been reading people, sensing opportunities, and detecting authenticity since you were old enough to notice when something felt off or felt right.

Trust it.

Take the student I met who saw busy college athletes struggling with dorm move-ins because they arrive weeks before regular students for sports. Her gut told her this was a problem worth solving, even though no market research would have pointed her toward "college athlete moving services." But she knew the pain point intimately—and that intuitive understanding is worth more than any focus group. She's listening to her clients' pain points and making adjustments in these first few years to get the processes more clearly defined before tackling a big marketing push. She's trusting her gut and testing strategies.

The Backwards Planning Revolution

Here's the thing about working backwards from your end goal—it forces you to get honest about what you actually want, not what you think you should want.

Start with this question: "What does success look like when I'm looking back on this in five years?"

Not revenue numbers or market share percentages, but the real picture. How do you feel? What impact did you make? Who did you serve? What changed because you existed?

I talked with a creative jewelry maker who's currently running multiple businesses to make ends meet. When we worked backwards from her five-year vision - running just one thriving jewelry business that she loves - suddenly her path became clear. She didn't need to perfect all three ventures; she needed to focus her energy on the one that aligned with her true vision.

Now work backwards. What needs to be true in year four for that vision to be reality? Year three? Next year? Next month?

This isn't just project planning, it's purpose planning.

And purpose is what separates you from everyone else doing similar work.

Write It Down, Make It Real

I told those students something I'm telling you now: If it's not written down, it's just a conversation you had with yourself.

Write down your story. Write down your gut instincts about your market. Write down what success looks like. Write down your backward-planned milestones.

But here's the critical part—write it down to hold yourself accountable, not to impress anyone else.

The most powerful business plans I've seen aren't the 40-page documents with perfect formatting. They're the handwritten pages that someone carries around, refers to daily, and updates based on what they're learning.

They're personal. They're honest. They're alive.

It's Not What Others Say—It's Who Trusts You

I've learned something powerful over the years: It doesn't matter what anyone says about you. What matters is who trusts you enough to be transparent with you, and whether you can reciprocate that same level of authenticity.

I met an engineering student yesterday who's working on something that could revolutionize how we think about community in small-town Iowa. He's developing a new model for American neighborhoods - big, innovative thinking that could genuinely improve how we live.

This is the kind of visionary project that should have him walking into every room with complete confidence.

But here's what he told me when I started asking about his whys. He didn't think he was eloquent enough because he speaks two languages and doesn't always know the best English word to use.

We stopped the session right there.

Here's someone reimagining entire communities, sitting in a room with some of the brightest entrepreneurial minds in Iowa, and his internal script was telling him he wasn't good enough - because he is fluent in two languages?

So I asked him to write this down: "I am eloquent. I can speak two languages very well. I'm sitting in a room with some of the brightest minds in Iowa. I deserve to be here because I have worked hard and I am an expert in engineering."

Because sometimes the most important marketing we do is how we talk to ourselves.

The Hundred Ways Principle

Here's what those students needed to hear, and what you might need to hear too:

There are a hundred different ways to market your business. A hundred different ways to analyze data. A hundred different "correct" processes.

And there is always SOMEONE else telling YOU how to market YOUR business because it worked for THEIRS.

I met a student yesterday who was beating himself up because he'd invested heavily in Google advertising after a convincing sales pitch from a "Google expert." The money was spent, the conversions weren't there, and he felt like he'd failed at the one platform everyone says you "have to" master. He wanted me to tell him to keep pushing and find the right algorithm on Google. He wanted me to help him find that perfect ad content and design.

Instead, I asked him a simple question: "If you tested it and it didn't work, why would you want to stay on that platform?"

Just because Google works for other businesses doesn't mean it has to work for his. He'd already found success on a couple other digital platforms. We are talking MILLION DOLLAR sales success - he's got an amazing product designed for houseplants that is ALREADY disrupting the marketplace! So why not move that BIG ad spend to what was actually working and stop worrying about what wasn't? Scale what works, even in marketing.

This isn't a weakness of business strategy - it's the beauty of it.

You don't have to find the one right way. You have to find your way. The way that aligns with your story, serves your gut instincts, and moves you toward that backwards-planned vision you wrote down.

Day 1 Lessons (With More to Come)

As I drove home from Okoboji last night, I kept thinking about the conversations that stayed with me. Not the ones with the most polished presentations or the most detailed market analysis, but the ones where someone's story broke through their strategy.

The Iowa Lakes Corridor gave me an OEI blanket as a parting gift yesterday, and I'm genuinely grateful for their thoughtfulness. But like the best gifts, it represents something much bigger than the item itself. That blanket isn't just fabric - it's woven from the connections I made, the innovative businesses I learned about, and the reminder that there are people here in Iowa making entrepreneurship a little bit cooler every single day. Just like the students' stories today, the real value isn't in what you can see on the surface.

And if I'm being completely honest, sitting in rooms with successful investors and business owners isn't just about what I can give - I jumped at this - because it's about what I can learn.

The vulnerability and personal connection I share with my clients and in those quiet coffee conversations? That only comes from staying curious, staying humble and recognizing that the best coaches are the ones still learning alongside the people they serve.

Today I'll be on a panel, tomorrow back to coaching. These students (and other business leaders) are teaching me just as much as I hope I'm sharing with them.

But if day 1 taught me anything, it's this: The businesses that truly matter aren't built by the smartest people in the room or those with the most resources. They're built by people who earn trust through transparency, who show up consistently, and who are brave enough to share what actually matters to them.

Your story isn't just how you differentiate - it's proof that you belong at the table, regardless of what anyone else thinks.

Following along with my OEI journey? I'll be sharing more insights as this week unfolds. Because sometimes the most powerful business lessons come from showing up authentically, even when your path to the table looked different than everyone else's. Disclosure: Iowa Lakes Corridor is a client of Vertical Marketing + Design.