Ep. 55 Roundtable: Best & Worst Business Investments

Feb 12

When January rolls around and I open up a fresh income and expenses spreadsheet, I can't help but think: what do I want to invest in this year?

Investing in your business is something I talk about a lot on this podcast. One of my most popular episodes has been about my best and worst business investments, and I see constant conversation on social media about what people are spending money on in their businesses and what they regret.

So today, I'm sharing a roundtable conversation with two of my friends, Jenn Green and Maddy Aucoin, about their best and worst business investments. We're not just talking about what they invested in—we're diving into what we can learn from their experiences.

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What the Community Is Saying

Before we jump into Jenn and Maddy's stories, I want to share some of the themes I noticed when I asked my audience this question on Threads. (I'll link the full thread in the show notes if you want to read every response—it's still one of my most popular threads to date.)

My prompt was simple: "What are the best and worst investments you've made in your business? The juicier, the better."

Here's what stood out:

Shiny Object Syndrome was everywhere. One person said their worst investment was "a fragment of a system that was shiny at the time," noting that having one piece of the puzzle isn't the same as investing in a solution. Their best investment was the relationships they're building. Investing time and energy into strengthening core connections with members, partners, and event organizers.

Team matters. One person's succinct response made me laugh: "Best investment was the right team, worst investment was the wrong team." Similarly, multiple people said their best investment was good business coaching and their worst was bad business coaching. We've all been there.

Memberships are hit or miss. One person said their best investment was a specific membership they named, while their worst was another membership they didn't name (telling, right?).

Financial help is worth it. Several people cited their accountant, bookkeeper, or tax person as their best investment.

And this gem: "Last year I invested in the services of a cold outreach strategist where she would teach me how to do cold outreach in a warm, not-spammy way. It was the worst and I so overpaid. My best business investment was probably Dubsado because I saved so much time on client onboarding now."

Now let's get into the specific stories from Jenn and Maddy, because I think there's a lot we can learn—not just from their investments themselves, but from how they've learned to choose what to invest in.

Jenn Green's Worst Investment: The Marketing Agency Disaster

Jenn Green is a funnel strategist and copywriter, and her worst business investment story is unfortunately not uncommon—but it's still devastating to hear.

"The worst investment I ever made in my business was hiring a marketing agency," Jenn shared. "I didn't hire someone off the street. This person was really well known in women-led online business circles, had a huge trust factor. And unfortunately, everything went downhill."

Here's what happened… They sent her the wrong copy for her funnel. They had bad ratios for her ad videos. They forgot to add a limit to her ad account, and she ended up with a $1,700 bill over one weekend before she could reach their emergency line to turn everything off.

"It was truly devastating. It cost me $15,000 and it took a long time for me to heal from that situation because I stopped trusting my choices and my decisions around the investments that I made in my business. I just kind of locked everything down. What should have helped me grow actually shrunk my business by quite a bit and left me in a hefty chunk of debt."

As a brand and marketing agency owner myself, I hate hearing stories like this. But unfortunately, they're not uncommon. Horror stories of well-reviewed, well-known agencies that just don't deliver happen more often than they should.

Jenn's case is extreme—literally everything that could go wrong did. But it's a good warning that when we're hiring people on the internet, no matter how much research we think we've done or how much trust they've built up, we don't always know what we're going to get.

This is why rock-solid contracts are so important, and why I'm a big fan of working with someone in a smaller capacity before investing in a $10,000 or $15,000 service. If Jenn could have done a smaller audit or one lower-ticket project with this agency first, she might have seen the red flags.

And as Jenn noted, experiences like this leave you jaded. They make it really hard to trust again, which affects your business long-term. Every time you need to hire somebody, you feel like you have to do extra vetting because you're nervous about getting burned again.

Jenn Green's Best Investment: Hiring Her Husband

Now here's where things get interesting.

"The best investment I ever made was to hire my husband," Jenn said. "Basically what I did was say, 'Hey, every time that you go to work for eight hours plus commute—10 hours a day—our family is losing money because my hourly is higher than yours. So what if you stopped going to work and you became the default parent of our family and I had time and space to actually grow my business?' And that's exactly what happened."

The results? "My husband is happier, my kid is happier, my business has grown exponentially since he's been able to take over that default role. And on top of that, we have moved our entire lives to Mexico because we have the freedom of myself running my own business and my husband not being tied down by a nine-to-five."

I love this one because it's a reminder to think outside the box when it comes to investing in your business. We often think about what we can outsource in our business—social media, bookkeeping, website design, copywriting. And yes, that's great.

But you could also outsource things in your personal life that would free up time for work. Maybe that's childcare, house cleaning, or even just using grocery pickup or delivery. (I'm not saying these are business write-offs—talk to your CPA—but they are investments that support your business.)

Investing in your business doesn't necessarily have to look like buying something or hiring someone directly for your business. Sometimes it's investing in other areas of your life that free up space—either time-wise or brain space—so that you can focus on your business and continue to grow.

Maddy Aucoin's Best Investments: Programs with Crystal-Clear Promises

Maddy Aucoin is a website copywriter and messaging strategist, and her best and worst investments follow a theme I've been seeing a lot lately.

"The best investments I've made recently in my business have been a data-backed marketing program and a branding program," Maddy shared. "And the reason I loved these so much is because I knew exactly what I was going to get from the program and the promise of the program was that I would walk away with very specific things."

The key difference? "The promise of the programs wasn't about making more money or something vague or generic. They were very focused and I knew exactly what I was going to walk away with. The other thing I really loved about these programs is that I knew I would get a lot of support from the people who were running the programs, which was really important to me."

As someone who has definitely fallen victim to shiny object syndrome—buying courses and programs without doing enough research—I think Maddy nailed it here. What made these programs great wasn't just the content. It was the clarity. She knew what she was going to get, and she knew her business needed it.

If you create courses, programs, or do group coaching, this is a reminder that even if you think your promise is crystal clear, you could probably make it even clearer. That would help you get more sales and have happier clients.

Maddy Aucoin's Worst Investments: Unaligned Communities and Events

"Some of the worst investments that I have made recently in my business have been unaligned communities and unaligned business events," Maddy explained. "And of course, you typically pay for these events or communities, but it costs you more than just money. It costs time, it costs energy, and overall, there is a lot that goes into being part of communities and attending events."

Maddy continued: "Networking is really important to me. I love meeting new people, whether it's online or in person, but I think there were a couple of things that I overlooked when deciding to be a part of these communities or sign up for these events. The first is that the marketing is typically very generic, focusing a lot on things like 'being in the room.' Of course it is important to meet new people and connect with new people through your business. But it's really important that you are spending your time, energy, and money meeting people who are actually going to help your business."

I'm a huge proponent that relationship building is one of the most important revenue drivers in your business, and I think Maddy would agree. But here's the thing: it's not just about how much the event ticket costs or the membership fees. It's also the time and energy you put in.

If you're forcing yourself to show up to things that feel unaligned because you think you "just need to be in the room," that's a red flag. Yes, being in rooms where your ideal clients are is good advice. But if it starts to feel forced or you're stretching yourself too thin, maybe it's not the right event or not the right season. And that's okay.

How These Experiences Changed Maddy's Approach

"Moving forward, I need to be a lot more discerning when I'm making investments into community and events," Maddy said. "Of course, there is a monetary cost typically associated with networking or going to events, but there's also the cost of your time and energy. Either way, you need to look cute if you're going in person—you need to wear pants and shoes."

She continued: "I am someone who falls very deep into FOMO. If I see a business friend is going to something, I want to go too. But this year I am going to focus on the data and focus on the events that I know actually move the needle for me. I am going to be doubling down on the communities and events that work for me, and I am going to be staying at home or closing my computer if there are things that sound tempting but aren't actually going to work for my business."

As a mom of two young kids, I deeply relate to this. It's hard to see all my business friends going to events, traveling, going on mastermind retreats—and I'm just sitting on my couch in my pajamas, working with kids playing at my feet. But that's okay. That's my reality right now, and it will change someday.

Maddy's advice to close your laptop and enjoy being at home instead of giving in to FOMO? That's a reminder we all need to hear.

The Big Takeaways

So what can we learn from Jenn and Maddy's experiences?

First, think outside the box with business investments. As Jenn showed us, your best investment might not even be directly in your business. It might be something that frees up your time or mental energy to focus on what matters most.

Second, do your research before hiring. Ask for reviews, request a test project, talk to past clients. Unfortunately, there are people who will take your money and not deliver. It happens to all of us at one point or another, and it's nothing to be ashamed about.

Third, don't let FOMO drive your decisions. We all want the shiny thing. We all want to do what everyone else is doing. But that's not a business strategy. Base your investments on data—what's actually going to drive revenue, free up your time, or get you to your next goal.

I'd love to keep this conversation going. Head to the Thread I mentioned and share your best and worst business investments. Let's keep supporting each other, celebrating what works, and normalizing the fact that sometimes we make investments that are kind of a bummer. That's just part of doing business.