Why Tim Grahl Had To Kill His Old Business to Find Real Success

This week, I talk with Tim Grahl, CEO of Story Grid and author of The Shithead, a novel that’s both thrilling and deeply personal. Tim made a name for himself as a book marketer who landed multiple titles on the New York Times Bestseller list at the same time. Tim’s work with Story Grid, alongside his partner Shawn Coyne, has guided hundreds of aspiring authors in mastering the essential elements of storytelling, helping them transform “I hope I can write a book someday” into a published reality. We cover a range of topics, from Tim’s journey as a book marketer to his insights on the power of structure in storytelling. We also dive into his personal experiences, including the impact of therapy on his growth as both a person and a professional. Tim’s work ethic and passion for meaningful storytelling are infectious, and I think you’ll find our conversation both inspiring and thought-provoking. Let’s get to it!

In this episode:

(00:00) - Intro
(05:06) - Tim's perfect vacation
(11:54) - Doing work that people don't understand
(15:19) - The "secret" to Tim's success
(20:34) - The moment Tim knew his business was broken
(31:06) - What is an object of desire?
(34:10) - The problem with online courses (and how to fix it)
(01:03:47) - Behind the scenes of writing a meaningful book
(01:13:37) - Success and the half warm beer theory
(01:18:03) - Reflecting on regret
(01:24:28) - How therapy changed everything
(01:32:58) - Chasing insight vs integration
(01:38:19) - Tim's beautiful future
(01:42:47) - Who Tim is becoming

Key Takeaways

Commit to High Standards and Hard Work: Tim shared how his early work experiences with his father shaped his approach toward hard work, and the importance of maximizing productivity in minimal time. This discipline translated into his business life, where he emphasizes outworking others and striving for excellence. Success isn’t achieved through passive income dreams but through relentless commitment, efficiency, and a willingness to tackle whatever challenges arise to keep moving forward.

Your Student’s Success is The Only Metric that Matters: Tim challenged the typical goal of online education by focusing not just on selling courses, but on ensuring student success. He advocates for a model where course creators take responsibility for participants’ outcomes, actively supporting their progress and making adjustments to help students achieve real results.

Sometimes You Have to Blow it All Up to Keep Growing: During difficult phases in his business, Tim faced the daunting realization that his company’s products weren’t resonating as he’d hoped. Instead of persisting on a failing path, he pivoted, refining his focus to align with his core mission, ultimately driving him to rebuild aspects of his business from the ground up.

When Your Career is “Weird, Find the Other Weirdos: Tim highlighted the value of surrounding oneself with like-minded people who understand and support unique career paths, especially in unconventional fields. He noted how these relationships can provide encouragement, fresh ideas, and insights that reinforce your sense of purpose.

Be the Hero: Tim talks about the concept of “heroic action” in life and business, encouraging listeners to push beyond comfort zones and avoid complacency. He discussed the courage it takes to make sacrifices, pursue meaningful work, and continue striving for excellence, even when it means risking failure or choosing the harder path.

Quotes

“If you want people to be successful, figure out how you can ensure their success and sell that. You'll go to bed at night knowing you helped everybody that gave you money. I’ve spent so much money on shitty writing courses. I can't be the person taking money from writers and not ensuring their outcome.” ~ Tim Grahl

“Regret is a weird thing. We can regret things we've done, but then we can also see how they were a stepping stone to get where we are today. There are things I've done that I wish I hadn't done, but at the same time, I learned an important lesson in my life.” ~ Tim Grahl

“It’s our responsibility as a company to get everybody that signs up to the goalpost of what we promised on the sales page. We're not done when we sell the course and give you the information. We're done when you have accomplished what we said you could accomplish. So, success is not selling the course. Success is 100 percent of the people completing successfully.” ~ Tim Grahl

“Every great story has what we call a double-factor problem. This is every real question in your life. Should I get divorced? Should I get married? Should I have kids? Should I not have kids? Should I write this book? The answer is, it depends on your context. It depends on where you're at in your life. Bullshit stories are single-factor problems, but they're really easy to fall for because they tell you all you have to do is X to solve this really complex problem.” ~ Tim Grahl

Links