Value of serendipity and saying yes

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What do you do when a business partnership fails? Do you try to engineer the perfect agreement so the exit is clean, or focus on alignment long before anyone signs anything? The truth is, most agency partnerships fail because owners rush into them without slowing down to see the cracks. Preparing for the worst is not pessimistic. It is how you protect the business you are trying to build.

Today's featured guest has gone through failed starts, broken agency partnerships, and overcommitting his time as the owner for fear of losing opportunities. He'll unpack 25 years of wins, mistakes, and hard earned clarity, from building his agency and how the biggest breakthroughs came from leadership shifts rather than marketing tactics.

Andy Crestodina is the co founder of Orbit Media, a Chicago based web development and optimization agency approaching its 25th year in business. Orbit has grown to a team of fifty five and more than eight million in annual revenue. Andy is also one of the most respected voices in content marketing, with millions of readers, hundreds of speaking engagements each year, and a reputation for teaching real strategy instead of recycled tactics.

In this episode, we'll discuss:

• Slow, organic for consistent agency growth.

• What a failed agency partnership can cost you.

• The hire that gives an agency founder their time back.

• Learning when "yes" becomes the problem.

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Sponsors and Resources

E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.

How Slow, Organic Growth Built a 25-Year Agency

Andy was working as an IT recruiter in the nineties and found himself bored at his day job. He didn't get to build anything in that position and he had a lot of ideation urging him to do something else. Luckily, the internet offered him that chance.

He could build a website and channel his creative energy through that side project. But could he do it full time? He had no resume and no portfolio to present to a potential employer. He realized it was easier to get a client to take a chance on him than it was to convince an employer to hire him.

So he and a high school friend started building sites. The first partnership failed fast and then the second attempt grew slowly, quietly, and steadily for 25 years. The secret was not paid ads or cold outreach. It was content. Consistent publishing, useful insights, and a commitment to organic channels long before that became mainstream advice.

When Agency Partnerships Go Wrong and What It Really Costs

There are many stories of successful partnerships in the agency world, but overall the disaster stories are much more common. As Jason says, you either know the bad partner or you are the bad partner. Andy lived through one of the toughest versions of that story.

He had three partners for a while. One of them ran an unprofitable department. Responsibilities were unclear. Values were not aligned. And when it came time to clean up the mess, a poorly written shareholder agreement became a bigger problem than the partner himself.

Andy had to mortgage his home and personally lend the company money to buy out the partner. The agreement used the wrong valuation formula. The partner dragged his feet and what should have been a difficult but clean process turned into a long, expensive, emotionally draining separation.

Looking back, Andy says something most founders never admit. A handshake would have been better than the shareholder agreement they had.

The real mistakes came earlier: saying yes to a partner who did not share the same values, not slowing down long enough to evaluate the deal, and being hungry for growth and ignoring misalignment.

The Leadership Hire That Gave the Founder His Time Back

Around this time of misalignment between partners was when a long time client turned management consultant stepped in. He saw tension inside the partner group, so he moved to do a 360 review and surfaced the problems that no one wanted to say out loud. Andy was quick to spot that he would be a great addition to the agency, and so eventually, he became the CEO.

That single hire changed everything.

Andy was doing all the sales and marketing. Meetings all day. Proposals all night. Burning energy on tasks someone else should have owned years earlier.

Once his new CEO came on board, he built systems, built a sales process, hired strategists to handle qualification and scoping. Suddenly Andy had 20 hours a week of his life back.

He poured that time into content and went right into work. He doubled publishing frequency, launched a conference, wrote a book, held monthly live events, shot videos. The brand exploded. Their reach multiplied. The inbound engine went from effective to unstoppable.

This is the founder shift so many agency owners avoid. Letting go. Delegating the work that drains you. Investing your best energy into the work that grows the company, not the work that maintains it.

Saying Yes, Saying No, and Protecting Your Energy

Andy admits he still overcommits. He still says yes to speaking engagements because he loves the stage and it generates leads, even though the constant travel wears him down.

This is something many agency owners have to face. You may want the brand, speaking gigs and reach. But you also want to protect your energy so you do not turn into the hero who disappoints people when they finally meet you.

At some point, you have to choose where your yes goes. Andy chose articles, newsletters, LinkedIn, webinars, a conference, and in person events. He let go of podcasting. He narrowed his focus so he could go deeper. That discipline, more than any tactic, is what keeps his inbound engine healthy 25 years later.

The Tension Between Culture and Profit

How do you balance loyalty to your team with the need for profit and EBITDA?

Andy is still trying to figure this out. His team has an average tenure of eight years. Some team members have been there twenty. Andy cares deeply about them and their families. But agencies face moments when bonuses, salaries, utilization, and capacity collide. Where doing right by people and doing right for the business feel like competing priorities.

There is no perfect answer. But there is a direction. Take care of your people first. Trust them to help you solve the profit problems. Fix leaks. Raise rates. Tighten scope. Operate like owners. And when the agency wins, let your team win with you.

Culture breaks agencies faster than anything else. Profit can be fixed. Culture cannot be patched over.

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