10 Timeless Business Lessons I Learned During My 7-Year Agency Career (And Why I Sold Mine)

If you haven’t heard the news, something special is happening here at SPI.

The team has officially forged as one. We’re upping our game with smarter and bigger plans for the future of SPI. (Hello, FlynnCon1!) And all of us as the collective “Team Flynn” community are invited to have a louder voice than ever to help empower entrepreneurs from all walks of life to create a lasting impact with their work.

Personally, I couldn’t be more excited to press start on this new chapter!

As Semisonic made famous during my youth, “Every new beginning comes from some other beginning’s end.” Ends are bittersweet. This one marks the end of my agency career, a seven-year span where I worked hard to build, run, and grow two different agencies (one as founder and CEO, another as partner and COO). Before that, I had a nearly seven-year career in enterprise IT where I led digital innovation teams building software in partnership with sales and marketing. (Wow, that feels like a lifetime ago. :))

Regardless of the workplace, my intention has been to build things of great purpose and value to others. Pat has always shared that sentiment. It’s one of the many reasons why we’ve become close collaborators and friends dating back to the good ol’ days of 2012.

It all started when I worked with Pat to develop and publish the first version of his Let Go memoir. (Link leads to Amazon) From there our collaboration expanded to include numerous other projects of different shapes and sizes as the years went on. And in 2015, we co-founded SPI Labs (creator of the Smart Podcast Player). These projects and business ventures electrified our discussions about purpose and visions for the future of SPI that gave rise to the intention to merge our two companies together.

All of those 14 years, and especially the last seven, have been a wild ride, one I’m so grateful for because it’s prepared me to become the COO/CFO of SPI, which is a true honor and proud moment to begin something new. I’ve learned a ton about business during these years, much from trial and error. I’ve also had tremendous help along the way.

I believe that a shared journey brings people of common values and like minds closer together. That’s where we are, Pat and I, together with our team. You’re a part of our team too. And you have inspired ideas for a business on your own terms that you can be proud of. That’s why I’d like to share some of my learnings with you—because I genuinely believe that they are relevant and useful for anyone who aspires to make a positive difference in the lives of others through the arts of business despite what industry they’re in.

At the end of this, I’ll share more about why it made sense to say goodbye to my agency career. For now, let’s dig in beginning with perhaps my favorite business lesson of all . . .

1. Your success is always, always, always a factor of how well you treat others, including your team.

To be an entrepreneur is to have an ego. That’s part of the terrain. At the cellular level, I think ego is good because it’s a required element to dream big and take bold action in the face of immeasurable difficulty and overwhelming odds. Your freelance career, tech startup, boutique agency, online business, or other venture doesn’t stand a chance without the drive that an ego provides.

But ego can quickly and easily mutate. Selfishness. Entitlement. Greed. Hubris. Vanity. Carelessness. These are among the dark and villainous manifestations of ego that threaten to overtake good intentions. The pain and suffering that can result comes in many forms. The central pain and greatest risk is the betrayal and alienation of those who have supported your success, because your success is always a factor of how well you treat others.

Who are the others? They are your clients and customers. They are your strategic partners. They are your investors. They are your co-founders and business partners. And they are, perhaps most importantly, your team—those whom you’ve rallied behind your vision, recruited to work hard by your side, and who have faith and trust in you.

To me, someone who cares deeply about servant leadership, your team is all you really have. Yes, you need a valuable product or service. Of course, you need product-market fit. Naturally, you need a differentiated brand. Yes, yes, yes. But making all of that happen to produce success is almost never a factor of one (meaning you alone). Being a self-made person is a myth. Our individual success is the direct, cumulative byproduct of how well we treat others who we’ve built relationships with and invited into our entrepreneurial journey.

If you’re venturing to start your own thing, or if you’ve already started and found traction, the best advice that I can give is simply this: work smart and stay humble. Build relationships based on value. Cherish your clients as if they are extended members of your team, because they are. Love your partners, because love is what we need to endure the rollercoaster ride of entrepreneurship. And never, ever take your core team for granted.

Related Recommended Readings:

1. The Go-Giver: A Little Story About a Powerful Business Idea (Link leads to Amazon)
2. Turn the Ship Around!: A True Story of Turning Followers into Leaders (Link leads to Amazon)

[Full Disclosure: As an affiliate, I receive compensation if you purchase through these links.]

2. A services business is a phenomenal way to accelerate your learning, especially as a leader.

Startups of all stripes are valuable learning environments. That said, I have found that those rooted in service offerings galvanize the deepest levels of learning usually at the most accelerated rates. Based on my experience here are some of the big reasons why service work has exceptional learning advantages:

• It makes you think critically about the value of your time and expertise and how to command that value in an open market.
• It challenges you to stay razor sharp on the latest techniques, strategies, technologies, and trends in your ever-evolving field.
• It pushes you to master communication, persuasion, influence, negotiation, and other soft skills across a diverse range of situations.
• It invites a wealth of relationship building opportunities that can kickstart a new career, open doors, lead to new ventures, and contribute to your growth and development.
• It is often an unpredictable ecosystem of adverse moments big and small that prepare you to be calm under fire, display empathy toward others, operate with confidence, effectively resolve conflicts, stay true to your core values, and remain humble.
• It is inherently rooted in feedback loops among your co-founders (if you have any), team, clients or customers, and extended partners that, when embraced, help you identify blind spots and mature your skills.
• It is a fantastic incubator of innovative ideas that may result in such things as a home-grown software product, educational product (e.g., a book or online course), or other creation.

You may think that a product-based business (such as a software-as-a-service [SaaS] company) affords these same learning opportunities. That’s true, though I believe that the pace (and sometimes the breadth) of that learning varies between the two models, especially when starting out. For instance, when heads down on a product, you can easily fall into the trap of not building enough value-based relationships, not seeking and receiving enough constructive feedback, and not placing yourself in enough situations that will test, develop, and fortify your leadership and management skills.

Related Recommended Readings:

1. What Sets Successful CEOs Apart (Harvard Business Review)
2. So Good They Cannot Ignore You: Why Skills Trump Passion in the Quest for Work You Love (Link leads to Amazon)

[Full Disclosure: As an affiliate, I receive compensation if you purchase through this link.]

3. Business partnerships are marriages that can be a “secret to success” when thoughtfully coveted and carefully cared for.

Having a business partner(s) is a great way to forge a leadership team for your business that is infused with the diverse aptitudes and perspectives needed to succeed.

Maybe you’re gifted at building teams, commanding finances, building product, and running operations and don’t crave the responsibilities that come along with being the front person/idea person who sells and markets your thing. If that’s true, then it may be wise to find a business partner who is gifted at marketing, has a knack for sensing new ideas and opportunities within your market, is a natural connector, and gets energy from helping others make a purchase decision to buy your thing.

Together, business partners can play more to their strengths than they ever could alone. They can help each other grow via the honest exchange of constructive feedback. They can hold each other accountable to their respective duties for the business and the results that they’re responsible for, empowering each other (and the business) to perform at ever greater levels.

When harmony sings between partners like that, it’s truly magic. That magic, however, isn’t always guaranteed. And even if that magic is found, it isn’t guaranteed to last. This magic is precious precisely because it’s hard to find and difficult to hold on to. It requires enormous trust, respect, empathy, commitment, and selflessness in the best of times and (especially) in the worst of times. That’s where the cliche comes from: business partnerships are marriages.

I’ve benefited from having different business partners in my career. Some have flourished and remain intact to this day. Others floundered and petered out without animus; it just didn’t work. In one instance, it cratered literally overnight due to a blind side betrayal. Despite the various outcomes of each, I’m grateful for those experiences. They’ve taught me a lot.

The most important lesson is that finding the right business partner can be a real “secret to success,” but only if you respect each other as equals, remain open and vulnerable at all times, don’t allow ego-driven insecurities and ambition to interfere, encourage healthy debate on ideas, and remain committed to a common framework of values that informs a shared vision for your business.

I encourage you to consider business partnerships as well. Proceed wisely, of course. Don’t rush into things, but don’t ignore the potential just because some relationships don’t work out. You could very easily be limiting your potential, and that of your business, if you staunchly take the position that you can do everything. Most people can’t. I can’t.

Related Recommended Readings:

1. Rocket Fuel: The One Essential Combination That Will Get You More of What You Want from Your Business (Link leads to Amazon)
2. How to Win Friends & Influence People (Link leads to Amazon)

[Full Disclosure: As an affiliate, I receive compensation if you purchase through these links.]

4. Your company culture is defined by how everyone on your team behaves, starting with you.

Many startups and early stage businesses (especially agencies) are plagued by good intentions gone wrong. Hustle as a work ethic is okay until it turns into 70-hour work weeks. Ambition is fine unless it spawns mistrust and infighting within your team. Everyone can have a voice, yes, unless that becomes justification for insubordination and entitlement. Flexibility is acceptable until it means no process, standards, or safeguards at all. Expenses are necessary costs of business until they include excessive entertaining with clients, unnecessary perks for leadership, and the like. Slack is a brilliant platform for collaboration until it mutates into an excuse to avoid doing the real work that matters.

If you’re the founder and leader of your business, you control your culture through your example. If you practice what you preach, and if you preach wholesome work ethics and values, then you and your company are well positioned for a close-knit, hard working, supportive, and productive culture.

That said, no amount of attractive window-dressing (e.g., a sexy brand name and logo, lavish office perks like foosball tables and free food, unlimited PTO policies) can save a company from itself if its culture runs counter to its stated principles and noble purpose. By “save itself” I don’t necessarily mean from outright ruin. There are plenty of companies that are wildly successful in an economic and market share sense that have abysmal cultures. Those companies often have high turnover of staff, sub-optimal profit margins, and less than stellar reputations.

I’ve committed some of these mistakes myself. For instance, I actually enjoy working and find it easy to put in way too many hours. And despite being a big process and systems guy, my instincts to help others and find compromise have led me to making choices that undercut the very operational capabilities I engineered in the first place. I try hard not to let these habits creep into the cultures I help shape and lead. It’s an ongoing struggle, as I know it is for my friends who also run companies.

So long as you’re not committing egregious behaviors, then learn from your mistakes without beating yourself up too much. Culture building is a contact sport. Take the hits, get better, and keep moving forward.

Related Recommended Readings:

1. It Doesn’t Have to Be Crazy at Work (Link leads to Amazon)
2. The Power of Habit: Why We Do What We Do in Life and Business (Link leads to Amazon)

[Full Disclosure: As an affiliate, I receive compensation if you purchase through these links.]

5. Leadership will be lonely, confusing, uncertain, frustrating, and overwhelming.

If you’re looking for an adventure in business, then leadership (especially of an entrepreneurial venture of any size and shape) is a great place for you. Just know going into it that despite the romanticism that surrounds leadership, the real feel isn’t all balmy sunshine.

Frankly, the cliche that “it’s lonely at the top” is remarkably true. You see and sense things that your team, clients, and even family members never will. Here are just a few ways in which you may experience the rollercoaster:

• The pangs of “imposter syndrome” in the early days as you wade ever deeper into the entrepreneurial waters.
• The insecurity that surrounds quitting your day job to go full-time on your business.
• The stress of paying yourself enough so that you can actually quit that day job or (if you already have) don’t have to abandon it in short order and return to a “normal job” to support yourself and your family.
• The agony of shepherding potential investors through a fundraising round if your business is in need of outside capital.
• The growing pains of feedback and self-discovery as you mature from just an entrepreneur into a capable business leader.
• The heartbreak that follows a business partner betraying your trust.
• The doubts that your brand is vivid and unique enough to stand out from the crowd, attract desirable clients (or customers), and develop a positive reputation that spreads.
• The panic that can set in when you lose a big client or account.
• The disappointment when a seminal team member resigns out of the blue.
• The uncertainty of business because you’re telling yourself “I’m good at my craft but I don’t know how to run a business.”

I have experienced most of those lows, and many others to boot. They can be devastating, even depressing. I nearly called it quits a few times. There were several moments in my career where it took everything I had to keep going.

I’m so glad that I kept at it. I hope you do too when you experience speed bumps. The highs are worth enduring the lows. Proceed with the comfort of knowing that it’s okay to feel not okay in such moments. Know that you aren’t actually alone. And believe that better days are ahead and fight for them.

Related Recommended Readings:

1. Leaders Eat Last: Why Some Teams Pull Together and Others Don’t (Link leads to Amazon)
2. Extreme Ownership: How U.S. Navy SEALs Lead and Win (Link leads to Amazon)

[Full Disclosure: As an affiliate, I receive compensation if you purchase through these links.]

6. Efficient and effective businesses do not run and grow on ideas alone.

If talk is cheap, then ideas are easy. That doesn’t mean ideas aren’t valuable. Every business needs a guiding mission with a clear vision, both of which are sharp, inspiring manifestations of ideas. And ideation should very much be interwoven into a culture that respects feedback, seeks the best ideas, solves the right problems, and promotes continuous improvement.

But ideas are only embers of the raging fire you see in your mind’s eye. To fan those flames, you don’t need more embers. You need accelerants.

Accelerants can come in many forms. Here are a few standard ones that I believe are applicable to most businesses:

• A structured business plan (supported by strategic plans) to transform raw ideas into manageable and executable concepts that produce intended results.
• Established processes designed to harvest feedback for selecting, planning, managing, and executing ideas.
• Talent recruited into the vision for your ideas who possess the requisite skills, attitudes, and intangibles to marshal those ideas into existence.
• Organized roles with clear responsibilities for everyone on your team (e.g., in-house staff, hired contractors, yourself) to reduce waste of resources and promote action across the team that “rows in the same direction.”
• Standard operating procedures in various functional areas of the business (e.g., finance) to safeguard against the downside risks of “idea creep” (e.g., uncontrolled spending on new ideas).

Accelerants are the gears of the business working together as its engine. Unfortunately, I find that the engines of many businesses are under developed. Ideas are rushed into execution with no real validation and little planning. Idea creep decays the focus of a business plan and leads to the wasteful spending of time and dollars. Endless ideation burns out the team. Executed ideas don’t assemble well into a cohesive business with a clear direction that others can follow that compounds growth. When in doubt, choose more accelerants over embers as that’s the course of action that leads to planned and controllable growth.

Related Recommended Readings:

1. Built to Last: Successful Habits of Visionary Companies (Link leads to Amazon)
2. Rework (Link leads to Amazon) and Remote (Link leads to Amazon)

[Full Disclosure: As an affiliate, I receive compensation if you purchase through these links.]

7. Operating fast and loose with your financial responsibilities creates a nightmare.

I could write an entire book about financial best practices for freelancers, entrepreneurs, founders—basically anyone who starts their own thing and tries to run and grow it largely or entirely by themselves. (Actually, I’m just wild enough to try that one day :))

For now, the key lesson is that if you’re a company of one, solopreneur, startup founder, or another derivative of an entrepreneur starting your own thing and looking to grow it, then you are signing up for a world of finance-related responsibilities whether or not you choose to think of yourself as a CFO or finance person.

Here are some of the core responsibilities I’m talking about:

• Forecasting revenue
• Developing budgets
• Invoicing clients (largely for service businesses)
• Setting up payment gateways (especially for product companies)
• Managing cash flow
• Organizing financial records
• Implementing a savings plan
• Calculating an appropriate salary and dividends for yourself
• Paying contractors, vendors, and other 3rd parties
• Running payroll (if you have a W2-based team)
• Instituting proper accounting practices

Operating fast and loose with these responsibilities is a high-stakes game of chicken where your business is on the line. Muck up just a few of these business functions and you can quickly find yourself in a living nightmare of unpredictable revenue, no cash reserves, an unknown burn rate, bloated fixed expenses, reckless discretionary spending, contractors clamoring to be paid (because their invoices have become past due), and more.

I’ve seen some of those nightmares up close. I’ve also heard loads of war stories from other agency owners, freelancers, and startup founders who worry to no end about making payroll, staying at least “cash flow neutral,” and paying themselves a just compensation.

I know finance isn’t everyone’s cup of tea, nor should it be. The realities, however, are inescapable. Start your venture with a finance co-founder, recruit a financially capable partner, or do something else if you don’t want to shoulder those responsibilities yourself. Otherwise, they’re on you.

Related Recommended Readings:

1. Achieving Financial Excellence: How to Master Finance for Non-Finance People
2. Profit First: Transform Your Business from a Cash-Eating Monster to a Money-Making Machine (Link leads to Amazon)

[Full Disclosure: As an affiliate, I receive compensation if you purchase through this link.]

8. Integrity is all you have and others will ask you to sell it for cheap.

Much of the business world operates on relationships. While relationships come in many forms, they all share a common ingredient: integrity.

Integrity can be gained. It can be lost. In the worst of situations, integrity may never appear or disappear entirely. How we choose and manage our relationships determines how much integrity rises, falls, or fades away.

Like most things in life, the ebb and flow of integrity is subtle, from one innocuous moment to the next. A small “just this one time” break with your better instincts just to close that next deal can start a downward spiral of perpetually accepting bad work. Conversely, a small and unexpected gesture of gratitude to someone who’s referred you work can begin the transformation of that relationship from a distant one into a deeper, more meaningful partnership.

And because it’s the small things that matter, it’s all too easy to accidentally fumble away your integrity for cheap. Here are just a few ways in which that can happen:

• A well-intentioned client asks for a one-time “favor” to slip in a discount or extra scope to a project despite saying that they respect your pricing as it stands. If you say yes, will you be able to say no the next time a favor is asked? And how do you manage the relationship so that it doesn’t become predicated on favors?
• A team member blows off some steam in a meeting in front of superiors or a client, or both, apologizes for it, and says that they’ve been super stressed lately and it won’t happen again. If you forgive that behavior without any form of reprimand and then that behavior happens again, do you forgive again without consequence?
• You and your co-founder or partner disagree on a course of action. Hopefully the debate remains rooted in respect and relevant points of view that should be addressed. But what happens if one of you slips up due to frustration and delivers an unjust character attack? Should the receiving party respond in kind? Should the slight be ignored?

Those are examples of seemingly benign incidents that may or may not trigger a pattern of bad behaviors. When those moments happen (because they will), call a quick sidebar in the conversation that’s occurring and handle it calmly. State your feelings without accusing the other party of intentional ill will, because that’s almost never true. And because they’re almost never true, you can successfully short circuit these incidents from becoming worse if you lean into them immediately when they happen.

Not all matters of integrity begin from such innocent origins, however. I’ve been around long enough to know that there are bad actors out there who are perfectly fine with and unapologetic about exploiting your integrity if they can get away with it. My general rule is that no relationship should ever make me feel bad about myself or uneasy about the work that I’m doing, and if anyone asks me to do something that doesn’t feel right, makes me feel like a lesser partner or person, or violates my values, that’s a red flag that requires me to speak up and take a stand for what I believe.

Related Recommended Readings:

1. Start with Why: How Great Leaders Inspire Everyone to Take Action (Link leads to Amazon)
2. Delivering Happiness: A Path to Profits, Passion, and Purpose (Link leads to Amazon)

[Full Disclosure: As an affiliate, I receive compensation if you purchase through these links.]

9. Major business decisions are just as messy, awkward, and scary as they are exciting, gratifying, and transforming.

Did you hear the news recently about Spotify’s huge acquisitions of both (yes, both!) Gimlet Media and Anchor.fm? Super exciting, right?! Personally, I’m stoked about what this could mean for the future of podcasting, a media form and industry I adore like many of you.

When big deals like this happen, they look awesome and glamorous from the outside. But while the Spotify-Gimlet-Anchor deals are truly electrifying, I believe it’s highly likely that those directly involved experienced high-stress, difficult, awkward, even tenuous moments along the way to closing those deals.

My deal with Pat to merge Winning Edits into Flynndustries had its touchy moments as well. There were never any heated arguments. But there were times when we had to discuss and debate very delicate and sometimes awkward topics in the search for common ground. As that search occurred, there were many nights when I couldn’t sleep. Central among my worries was what might happen to my relationship with Pat if the deal fell through for some reason. And at some point, it’s difficult not to think that you’ve passed some point of no return, which only magnifies the stress of it all.

Thankfully, our negotiations throughout remained rooted in integrity, fairness, and even vulnerability. As such, we struck compromises and found common ground, arriving at an exciting outcome that powers the future vision for SPI. The sleepless nights, long conversations, exhausting days, and moments of doubt were all very worth it.

Deals aside, when you’re in the chair that is responsible for the business, you’ll encounter a lot of high-stakes decision points, such as:

• Hiring key talent with associated high levels of compensation
• Firing underperforming individuals and even misbehaving clients
• Investing serious capital (your own or others) to fund a new venture
• Developing business models and strategic plans that at best may work
• Negotiating expensive office space for your growing team
• Spending tens of thousands of dollars to attend an expo or event
• Investing in your team and culture with expensive benefit programs
• Conducting a local, regional, or even national tour to promote your thing
• Orchestrating a live event of your own for dozens or hundreds of people

If you have ambition for the top job, great, just be ready for the sausage making. Big decisions are always difficult and messy. That’s why they’re big. When they work out, they’re among the most joyous and gratifying experiences you could hope for as an entrepreneur and leader.

Related Recommended Readings:

1. The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers (Link leads to Amazon)
2. Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist (Link leads to Amazon)

[Full Disclosure: As an affiliate, I receive compensation if you purchase through these links.]

10. Entrepreneurs are never done, even when big things end.

Does the conventional idea of retirement appeal to you? Yeah, me neither.

I’m not exactly sure when I figured that out about myself. If I had to guess, it was around 2007. I had just completed a two-year leadership development program to start my enterprise IT career after college. And I had just read Tim Ferriss’ landmark book, The 4-Hour Work Week. Both influences gave me new perspectives about the boundaries and opportunities of work, the ability to create positive change for others in one’s career, the growing influence of the web and other technology innovations, and the outsized impact potential of leadership. [Full Disclosure: As an affiliate, I receive compensation if you purchase through this link.]

I remained in enterprise for another four-ish years. I relished every moment and learned a lot. Then, when a tipping point opportunity presented itself, I took the leap and ran full force into my own thing. Now, seven years and several “things” later, another inflection point has happened. The agency days are over. But as before, I’m not done. I’m running full force to support the amazing SPI community and the inspiring vision we have for its future.

The tipping point that motivated Pat, me, and the team to forge together is easily explained: We share a common vision to empower entrepreneurs with the teachings, tools, and confidence to succeed, and due to the growth of the SPI brand and business (and the demands that come along with such growth), a devoted in-house team was necessary to go after that vision in a responsible way.

The opportunity to support my team’s growth (and my own) through a more focused, deeper concentration of work was wildly appealing. Agency life is great and rewarding. It challenges you like crazy to get good and stay sharp. It can also easily distract from your and your team’s own growth and development as you intake ever more service work. Going in-house with Pat, whom we couldn’t love and admire any more than we already do, plus the privilege to serve the SPI community was a profound “hell yes!” opportunity.

Honestly, I don’t think I’ll ever be done. I wager you feel the same way. I find that many (if not most) entrepreneurs share that impulse. Call it hunger or drive or ambition or sense of duty, something is there that motivates us to continue to do hard, necessary, and rewarding work. I call it simply playing for the love of the game.

Related Recommended Readings:

1. Drive: The Surprising Truth About What Motivates Us (Link leads to Amazon)
2. The Tipping Point: How Little Things Can Make a Big Difference (Link leads to Amazon)

[Full Disclosure: As an affiliate, I receive compensation if you purchase through these links.]

If you’ve made it this far, thank you! I’m genuinely grateful and I’m curious to hear from you. Which of these lessons resonate most with you? Which do you disagree with? Which are you keen to learn more about? This article is just the start of many conversations I hope to have with you here. Let’s keep it going in the comments!

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