How to Keep an Agency Partnership from Blowing Up with Andy Crestodina | Ep #865

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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