You Gotta Know When to Hold ’Em

I heard the old Kenny Rogers song, The Gambler, the other day, and I couldn’t help but think how much it applies to entrepreneurship.

Business isn’t necessarily gambling, but there are definitely times when you have to look at what’s on the table, read the room, trust your gut, and decide what the next move is. The longer I’ve been in business, the more I realize that growth isn’t just about getting more opportunities. It’s about knowing which opportunities are actually right for what you’re building. That sounds simple until there’s money and opportunity attached.

Sometimes an opportunity looks REALLY good. The meetings go well, they have the budget, and everyone is excited. On paper, it looks like something you should say yes to. But a good opportunity and a right opportunity are not always the same thing, and as business owners, we have to learn the difference.

Before we take something on, I’ve learned to slow down, think through things, and ask questions. Can we actually deliver this to our standards? Do we have the systems, team, capacity, and structure to make it successful? Does this make sense for our business right now and in the future? Who benefits from this, and is that benefit mutual? Does it fit our mission, culture, and values?

Know When to Hold ’Em

We had a potential opportunity come up that could have been a great contract. A municipality wanted help running a food access program, which is something we care deeply about and a major part of our mission. Not going to lie, I was pumped and things were moving forward.

But once I really looked at the structure, it didn’t feel like the right time. They didn’t yet have the foundation in place to make the program as impactful as I felt it needed to be for the community. I felt like we would have been charging for a program that sounded good in theory but wouldn’t have delivered the kind of impact the community deserved, and that didn’t sit right with me.

Could we have taken the check? Yes. Would it have been the right thing to do? In my opinion, no.

So I was honest. I told them I didn’t think it was the best use of their resources right now and offered to revisit the conversation next year when the foundation was stronger. That’s what holding looks like to me. It wasn’t a no forever, it just wasn’t the right time.

Those decisions aren’t fun, and nobody throws you a party for turning down an opportunity. But those are the decisions that build trust, protect your reputation, and align with how you want to run your business and the culture you want to build.

Know When to Fold ‘Em

There are also times when you fold because the values don’t align.

We have turned down support before because the fit was not right. That can be hard, especially when you are trying to run programs, pay your team, build something from the ground up, and trying to make every dollar stretch. But money does not erase misalignment and a sponsorship check does not magically make something a good fit.

If a company is publicly handling things in a way that goes against our culture and values, we pay attention. Me, our team, our board. That does not mean people or companies cannot grow, change, or do better. I hope we all can! But if the alignment is not there right now, then we’ve decided we fold. Maybe we play another round in the future, but today, we are out.

Know When to Walk Away

A few years ago, we had what seemed like a great partnership with a venue for our artisan markets. The markets were successful for us, for the venue, and for the vendors. I genuinely liked the people we worked with, and I believed we were building something that made sense for everyone involved.

But we did not have a contract, and that’s on me and a lesson I learned the hard way. Everything was built on conversations, trust, and what felt mutually understood. It was implied that we would continue working together. We had even started talking about dates for the following year.

Then we were cut out. Not in a meeting, not face to face, through an email. Total ‘Carrie Bradshaw getting broken up with on a Post It’ vibes. 

I’m not going to pretend it didn’t hurt. It did. I felt blindsided, embarrassed I didn’t have a contract and I honestly felt like I had been stabbed in the back by people I genuinely liked and respected.

I could have gotten publicly or fought to save it. I could have tried to explain our value to people who had already decided they didn’t value us, or I could have sent the perfectly crafted backhanded email (my specialty)....

But instead, I let it hurt, I felt it, and then I walked away.

At the time, it felt like a loss. Looking back, it was one of the best things that could have happened. If that door had not closed, I may not have said yes to the opportunity to help revitalize a struggling, long-time farmers market. That opportunity turned into Farmed & Forged, one of the things I’m most proud of in my entrepreneurial journey. 

Sometimes a door closing is not the end of the story and is the thing that moves you toward what you were actually meant to be doing. I would not have chosen the way that situation played out, but I can see now that it pushed us toward something bigger, more aligned, and more impactful. Plus I learned some valuable lessons that I’m glad I learned earlier rather than later. 

Know When to Run

Not dramatically like flipping a table Real Housewives style, or setting social media on fire. Just quietly removing yourself from something that does not feel right.

Sometimes people invite you into things with an ulterior motive. Sometimes they use your name, your relationships, your credibility, or your work in ways you do not fully understand until you are already in it. Sometimes someone is offering a lot, giving a lot, saying all the right things, and you cannot quite figure out why. I’ve learned that is usually the moment to pause and ask more questions.

What is the real goal here? Who benefits from this? What am I being pulled to? What am I lending my name, time and energy to? What is expected of me that is not being said out loud?

If the answers feel off, trust that.

Not every red flag shows up waving itself in your face, I’ve found a lot of times it shows up with a friendly smile and an offer that seems too good to be true. Sometimes it looks like an opportunity that is moving a little too fast for you to see what's really going on. And sometimes it sounds like “this will be great exposure,” which, as every business owner knows, usually means someone is about to ask you to do a lot of work for very unclear benefit.

No thank you...respectfully.

It is easy to chase every opportunity, especially when you are ambitious, driven and trying to build your dream. It seems harder to slow down long enough to ask whether the opportunity actually fits your business, the mission, your team, and the season you are in.

The Real Lesson

One of the biggest lessons entrepreneurship teaches you is that not every opportunity is meant to be taken.

Sometimes you hold because the timing isn't right. Sometimes you fold because the alignment isn't there. Sometimes you walk away because the cost is greater than the benefit. And sometimes you run because every instinct in your body is telling you something your brain hasn't fully put into words yet.

Success isn't just about knowing when to say yes. It's about having the discipline to say no.

Sometimes the smartest move isn't taking the deal at all, sometimes it's leaving the table with your integrity, your reputation, your team, and your peace intact.

-Mandy