Entrepreneur loses $60k over a handshake deal with his best friend and business partner: 'Lost the money. Lost the friend.'

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Ben Weiss • Writer and Editor
Jan 20, 2026 2:00 PM EST

Here's a friendly reminder to get all agreements documented in writing, even if you're working with your best friend.

We've all seen how this dynamic plays out in business and in life. We saw it in The Social Network. We probably know examples in our personal lives. Two besties get into business with one another and expect their working relationship to remain strong and steadfast regardless of the obstacles that may come. However, the lack of predictability when it comes to business makes it pretty impossible to know with absolute certainty that a friendship can withstand the trials and tribulations of entrepreneurship.

Of course, many working relationships can succeed against these odds, but it takes transparency and fairness for these relationships to overcome these hurdles. This young entrepreneur started a small business startup venture with his best friend and fellow college students. He provided the technical expertise, while the author provided connections and initial funding. Their understanding was that any profits would be split 50/50. However, they made the eternally naive mistake of failing to get any of that in writing.

By the time the company actually started to earn money, the author's so-called "best friend" and co-founder suddenly had a change of heart regarding how profits should be divided between them. He felt that his contributions to the company were far more valuable and ended up claiming 70% of those earnings. Talk about betrayal!

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  • We all know people in our lives who have spoken with regret about professional mistakes they might have made that haunt them for years. While we hope that this author gets back on his feet and learns from these egregious errors, it's difficult not to feel like he's going to be haunted by this mistake for a long time. 

    Still, he knows better now, and here's hoping that there are other aspects of this professional experience that he can look back on fondly. After all, he's a young professional with plenty of time to recover and improve. Ideally, he'll be able to reflect on this chapter of his life as a formative moment from college rather than a missed opportunity to make it big at a young age. 

  • Two men stand outside a corporate building.
    via Vitaly Gariev

    Image is representative only and does not depict the actual subjects of the story.

  • "Trusted a handshake deal with my best friend. He denies it ever happened. Lost $60K."

    Built a project together with my best friend from college. Never bothered with contracts because we trusted each other completely. Worked together for eight months. The project started generating real revenue. His
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  • contribution was technical. Mine was business development and the initial capital. We'd verbally agreed to a 50/50 split once things were profitable. Nothing written. Why would we need that between friends. Didn't even document our agreement
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  • properly, just had some rough notes in a Google Doc that we never formalized.When the first real check came in he suddenly remembered the agreement differently. His version had him at 70% because "the tech is the real value." My version was 50/50 as we'd discussed multiple times.
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  • No documentation existed either way.Tried to work it out. Couldn't. He controlled the codebase and eventually locked me out entirely.
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  • The $60K I'd invested and the months of work I'd contributed were just gone. Had to throw together a pitch deck for potential investors to try salvaging something, used an presentation generator because I needed it done fast, but nobody wanted to invest in the legal mess. Taking legal action would
    via Intrepid-Degree-6612
  • cost money I didn't have for an outcome that was uncertain.Lost the money. Lost the friend. Learned that handshakes mean nothing when money gets real enough to matter.Every partnership needs documentation. Every agreement
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  • needs writing. Not because you don't trust the person but because people genuinely remember things differently when stakes are high. The contract isn't about distrust. It's about clarity.
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  • Two men celebrate outside a modern office building.
    via Vitaly Gariev

    Image is representative only and does not depict the actual subjects of the story.

  • AuthorityAuthor I'm sorry this happened. Hard lesson learned. I'd still have a free consult with an attorney. $60K would be worth it. I'm not an attorney, but they'd have expert advice on your options.
    via Intrepid-Degree-6612
  • PainterOfRed ⚫ This happened to me when I was young. I did go to an attorney. I gave him a "not to exceed" number for his time and effort to help. I gave the attorney plenty of leeway to
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  • speak for me because I didn't want to even think about it. He started with the "stern letter" then it progressed to setting a court date. Just before court, I got a check covering
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  • my initial investment and attorney's fees. Much of the time I put in to the biz was a wash but it felt better to get something back.
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  • Meanwhile, I'm so sorry about you having to experience that. The betrayal is horrible. You'll heal and cover yourself better next time. Don't get too jaded. Also - this is still very real and valuable experience. All of it.
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  • RDW-Development Yes. Partners s . Get it in writing. Don't even need a lawyer- just a document describing the arrangement. This guy is a d lead and a crook. Long term he would have caused more problems.
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  • Natural-Ad-9678 . There are no friends when it comes to business. Put it in writing or it's a risk you take, like going to the casino
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  • desert_jim The great news is without a contract there's nothing preventing you from forming a company and taking all the clients to your new platform.
    via Intrepid-Degree-6612
  • You know what was important to those customers because you worked with them to bring them on. He didn't, he's severely devaluing your contributions to the business. And if the friendship is toast at this point you won't be out anything.
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  • AgentPyke You don't have money and your ex-friend who is barely making money doesn't have money. Sue him. Get what's yours.
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  • Technical geeks often don't ever understand or appreciate the hard sales. But you also put initial capital in. Get your money,
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  • you more than anyone (more than his sweat equity) are owed money. You could have hired anyone for the code base. Not anyone can provide the money or the business development. That, in reality, is harder.
    via Intrepid-Degree-6612
  • Two men shake hands outside a corporate building.
    via Vitaly Gariev

    Image is representative only and does not depict the actual subjects of the story.

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friendship entrepreneur startup friends business money college entitled people
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