Key Takeaways from Ryan Klee’s Conversation on the Side Hustle to Small Business Podcast
When I sat down with Sanjay Parekh for The Side Hustle to Small Business Podcast, we covered a lot of ground — from my early days as a would-be baseball player to the adventure that’s been Rootstock’s journey over the past eight years. But what struck me most as I listened back was how often we arrived back to the same truth: real business growth comes from real human connection.
Here are five insights from our conversation that I hope resonate with you, whether you’re thinking about starting your own thing or you’re already deep in the entrepreneurial trenches.
1. You Never Know What Could Happen — And That’s the Point
When people talk about entrepreneurship, they usually mention the fear. And yeah, it’s terrifying. You never know what’s going to happen when you leave the security of a steady paycheck and venture out on your own.
But here’s the thing: flip that fear on its head and inject it with some potential. You never know what could happen. Who you might meet. What collaboration could emerge. What direction your business might take that you never imagined.
That reframing — from anxiety to possibility — gave me the courage to make the jump. I didn’t have a perfect business plan (or really, any business plan). I had a couple of side hustle clients and a belief that staying curious about what might unfold was better than playing it safe and doing work that was fine, but not truly what I wanted.
The relationships I built early on? Some of them are still feeding Rootstock today. That’s not strategy, that’s what happens when you stay open to connection.
2. Great Ideas Die in Isolation
I joined forces with my co-founder Tom Bell because we kept grabbing coffee. Just two people trying to figure things out, sharing what we were working on, supporting each other. Those casual conversations eventually led to Chronicle and Ryno Media (my first company) working together, and ultimately, forming Rootstock.
Creating anything requires an entire ecosystem of people and talents who find each other, communicate who they truly are, and work together from that foundation of connection. That’s not just true for businesses; it’s true for any creative endeavor, any movement, any meaningful change.
Every big thing is just a collection of smalls, and a lot of those smalls come from other people.
Don’t try to do it alone. You can’t. And honestly, you shouldn’t.
3. Consistency Beats Perfection
Here’s something I admitted on the podcast that I don’t talk about much: I’m not naturally a social media person. I love being social in person, but posting on LinkedIn? That’s work for me.
But here’s what we see all the time, and it applies just as much to me: the biggest challenge people face is consistency. It’s not having the perfect post, the perfect strategy, or the perfect brand voice. Just showing up and doing the work is enough of a challenge.
So every day, do one thing to get you closer to your goal. Write one LinkedIn post. Send one email to a prospect. Have one conversation. It doesn’t have to be massive. Those little smalls add up to the big.
I’ve learned this the hard way. When times were good at Rootstock, we stopped doing business development. We assumed the deals would keep coming. Then we lost two anchor clients within a month of each other, and suddenly we were in panic mode.
Now? Our pipeline is fuller than it’s ever been; not because we got lucky, but because we committed to showing up consistently, even when it’s hard.
4. True Thought Leadership Serves the Community
A lot of people think thought leadership is about being the smartest person in the room. And yes, while there’s a certain level of knowledge, experience, and expertise required to be considered a thought leader, there is a difference between that and a subject matter expert.
A subject matter expert has deep knowledge. That’s valuable. But a thought leader takes that knowledge and asks: How can my thinking elevate the entire field? How can what I know make everyone better?
Thought leadership only means something when it exists within the context of community. You don’t become a thought leader by declaring it; you earn it by sharing your insights in ways that move your industry forward, that help other people thrive, that create value beyond just your own business.
This is why we start every client engagement with deep conversations and curiosity-driven discovery, by articulating cornerstone story truths, and by crafting a relationship-centered strategy. We’re not jumping straight to content. We’re uncovering the thinking that actually matters — the ideas that will create real impact on all the execution.
5. People Want to Help.You Just Have to Ask
This one’s simple but profound: don’t be afraid to ask for help.
I used to think I had to figure everything out myself. That asking for help was a sign of weakness or that I was bothering people. But the truth is, people want to support you. They just don’t always know how unless you tell them.
When I started Rootstock, I leaned on mentors, friends, former colleagues, even clients. I asked questions. I asked for introductions. I asked for feedback. And guess what? People showed up.
Your network isn’t just about what you can get from it, it’s about the mutual support that happens when people genuinely care about each other’s success. That’s the kind of community I want to be part of. That’s the kind of community Rootstock helps create.
So if you’re sitting on a dream, a side hustle, or a scary next step: talk to people. Ask colleagues in your industry how they did it. Ask your family for support. Ask a new connection for coffee.
You’ll be amazed at what opens up when you just ask.
Final Thought: Do Cool Shit With Cool People
At the end of the day, that’s what this is all about for me. Life is too precious not to spend it building things that matter with people you genuinely respect and enjoy.
Creating communities of empowered leaders who lift each other up is what gets me out of bed in the morning. And if we can help professionals build brands rooted in authentic connection, in service to something bigger than themselves? Well, that’s exactly the kind of cool shit I want to keep doing.
Want to hear the full conversation? Listen to the episode here. And if you’re ready to dig into your own Kernel of Truth — your authentic story that fuels your business—let’s talk. You can find me on LinkedIn or at rootstock.agency.