I f*cked Up

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Most of the best lessons I’ve learned about building teams and business didn’t come from textbooks or management blogs—they happened in real life, often in a booth over coffee, trading stories with friends who know what it means to risk time, sanity, and cash just to keep the lights on. If I sound like someone who’s failed a few times, it’s only because I’ve lived some things: hired too soon, invested in people with big promises, moved roles around hoping for magic.

This isn’t theory—it’s a reflection with grit, heart, and some real scars.

Why Failure and Vulnerability Really Matter
(From My Own Messes)

When you’re running a small business, mistakes aren’t just a possibility; they’re practically mandatory. Every bold move carries a lesson. Back when I hired my first real sales expert, I thought I was setting up for a home run. He built out a fool-proof offer, dialed in a call structure, and brought genuine sales discipline to our ragtag bunch. But I brought him in too early—didn’t have enough inbound volume to keep a high-value closer busy or justify the cost. It was humbling and awkward, but through the struggle I found out what pieces were missing, and he helped carve a playbook I still use.

Another time, I went all-in on paid acquisition and content. Built out a team of smart, creative folks—paid up front and burnt a chunk of our war chest. Trouble was, I didn’t have the machine ready to turn their stellar content and campaigns into actual offers. They delivered, but I couldn’t convert it into business that stuck. That hurt. Payroll went out, but the engine waited. Learned a lot about timing and what teams actually need.

Probably the most personal story, for me, is moving my chief of staff between companies. I’ve seen them tackle everything from customer work to sales and partner conversations. Sometimes it worked, sometimes it didn’t; but I keep coming back to the idea that creating new opportunities together—even after the role changes—means betting on people over titles. The hope is that the long-term relationship, tested through a lot of restarts, will pay off.

Mistakes like these don’t always make the numbers look great. Sometimes the business is less profitable, sometimes team morale dips, and sometimes things need a hard reset. But—if I’m honest—I’d rather walk through those failures and learn than pretend they don’t matter. Vulnerability with my team and my partners isn’t weakness; it’s what lets folks stick through the hard times, bring ideas forward, and build something better when the chips are down.

Evaluate Talent and Needs

Forget institutional jargon—here’s my tested, lived guide for figuring out what kind of folks and skill sets a scrappy business really needs.

Step 1: Know What’s Actually Missing

Before hiring, sit down and make a list of business bottlenecks. Ask:

• “What can I, personally, not get to this week that would unlock sales, operations, or saves us from pain?”

• “Is it time for technical firepower, hands-on customer service, or fresh creative?”

I’ve wasted the most money hiring talent ahead of this list—just thinking “more hands” would equal more progress.

Step 2: Build a Simple Talent Matrix—Attitude vs. Aptitude

There's no magic formula, but I roughly sort folks on two axes:

• Attitude (Culture, Grit, Humility): Do they want to build? Can they weather storms and laugh about failures? Will they challenge me respectfully?

• Aptitude (Role Mastery, Results): Can they actually deliver what we need—now, not hypothetically in a year?

The best hires for small shops aren’t always those with the shiniest resumes; they’re the ones who show up, try hard things, admit what they don’t know, and learn with us.

Step 3: Phase Talent by Business Milestone

Over time, what you need shifts:

• Early days: Hire visionaries and utility players—folks who love trying many things and don’t mind lack of titles.

• Growth phase: Specialists with clear skills (sales, ops, dev, marketing) who operate independently.

• Mature phase: Process nerds and leaders who want to mentor, scale, and set new standards.

Most of my hiring fails came from shooting for “A-players” before I had roles or systems good enough for them to thrive. Infrastructure wins, not hero moves.

Step 4: Give Room for Real Collaboration—Don’t Box People Early

The only way to really know if someone “fits” is to work together. Bring candidates in for projects or trial runs. Let them own a problem for a few weeks.

• Do they ask good questions?

• Do they look for feedback?

• Do they handle changes without drama?

In my experience, someone’s real strengths and weaknesses show up quickly if you let them fail fast and recover with support.

Step 5: Make Feedback Relentless—But Not Cruel

Keep conversations open. When moving people between companies or roles (like my chief of staff), make sure they know it’s a learning curve—not a permanent judgment. As long as people are honest about what’s working and not, progress usually follows.

Step 6: Watch Out for These Talent Traps

• Hiring big-company talent for a small-business mess: I tried bringing in closers before my funnel was ready. That didn’t work—everything got bottlenecked and cost shot up.

• Keeping a misfit on payroll out of loyalty: Loyalty is good, but sometimes it locks everyone in place and slows learning.

• Assuming paid acquisition fixes core offering gaps: Couldn’t turn campaign or content wins into cash—a painful lesson.

Step 7: Keep Learning and Adjusting

No talent plan survives first contact with the business plan. Treat team building as iterative—check quarterly if the roles and responsibilities still make sense. Don’t be afraid to hit reset or move people around if skills aren’t matching the moment.

Stories from the Trenches

These examples aren’t just stories—they’re the context for how I decide what to try next.

• I hired a sales expert, built an airtight sales structure, and learned what it takes to close deals. But by hiring too soon, I ended up with a payroll line that pressured every other part of the business. It taught me to map out my lead flow and timing before going after senior talent.

• My paid acquisition and content development team delivered high-quality assets. The problem was mine—I didn’t have the right offer structure or conversion engine ready to catch their success and turn it into actual customers. The lesson? Don’t build out a full team for demand gen if the product isn’t ready for scale.

• When moving my chief of staff between companies and roles, what stuck out was her ability to try new things and adapt. Sometimes she was the anchor, sometimes she was a spark. What matters is keeping that opportunity wheel turning, not forcing someone to fit one mold.

Every misstep made the next hire better. Every vulnerable conversation opened new solutions. Employees who stick with me through hardship, who challenge my assumptions, and who build resilience—those are the ones I bet on, even if it’s not always easy on the bottom line.

Wrap Up: Building Success is Messy, But Worth It

If there’s one thing I’d trade fancy frameworks and best practices for, it’s sitting down with friends and sharing what went wrong, what stung, and what’s still worth trying. The secret to surviving and thriving as a small business owner isn’t avoiding pain—it’s using it as fuel. Vulnerability doesn’t mean weakness; it’s the glue that keeps good people together during pivots and chaos.

Building teams and testing talent isn’t a straight line. Hire for learning, for attitude, for the willingness to put up with your faults and their own. Only through struggle do real opportunities emerge—for employees, for founders, and for the business that follows.

So next time you’re thinking about your next hire, don’t just ask if they fit a job description. Ask if they’re ready to share the hardship, laugh through the mistakes, and learn alongside you. That, for me at least, is the only way the job stays worth doing.

Hire for those investing in you.

What mistakes or lessons have you learned in building out your companies? Please reply and share because these lessons can be softened with others.

Have a great finish to your week.
-Grady

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