Never Start A Company With The Woman You Love

I am a serial Entrepreneur. It is the only thing I have ever wanted to be. While other kids would say that they wanted to be doctors, lawyers, or some other noble well-paying profession. I would say that I wanted to be a business owner. I wanted to create a huge mega-company that everyone needed, even if they really didn’t.

I have succeeded in being an entrepreneur. I have succeeded in starting companies. I have lived an interesting life, but my biggest mistake in all of them: Is that I started the companies with the women that I loved at the time. All have failed, when the love failed.

Today, I find myself at an interesting crossroad. I have a thriving company. Growing, profitable and developing new opportunities. Not quite a pivot, but our market expertise puts us in a position that brings other companies to us. We are not innovating (it is too expensive). We are building a tried and true business model that builds on our reputation. Only, I work with the woman I love, but she does not love me anymore…at least not the way that she did … not the way that I love her.

I have made my mistakes. I am not saying that I am without cause of the situation. I got frustrated, stressed out, drank too much, put on too much weight, but every day I showed up and I worked.  I put in 12 to 18 hours, 6 to 7 days a week. Building a business on cash flow only is hard (we have little debt). It is really fucking hard when you have rent, bills, credit cards, College loans, and all the other shit that everyone tells you need to have to be “successful”.  Fights occur, and you lose your way.

Today, the business turned a corner, and I want to quit. I want to walk away from it all, because she does not love me the way I love her and I know it is my fault. I hate social media, but have to use it.  Every day, it reminds me of my failure. It makes me so jealous that it causes a pain like a red hot dull spoon digging into my soul. Not because I know what she is doing, but because I don’t.

She did not talk with me, she just unfriended me … Blocked me completely. It was sudden. I just stopped getting her updates and suddenly could not see her social profile. But we still own the company together.

I hate social media. I hate Facebook. I hate Instagram. I hate all those people who are able to spend their days running in some beautiful place and (un)humble brag about their leisure. I want to scream at them in Hashtags….#IsPigLatinForTheShallowandStupid, #Ifuckinghate#s, #youneverpostaboutyourboringasgonowherejobs, #werkbitch, #Imissmylove.

But I can’t, as I have a company. I have users, I have potential users, investors, and social media meltdown is a #PsuedeSucide. I cannot even turn it off, so it reminds me every day…digging that hot fucking spoon through my skin, up under my rib cage and into my heart…reminding me that the woman sitting next to me, the woman I started this company with, the woman that I love more than anything in this world….does not love me the same.

I lost the weight, I have turned the company around, I have worked near miracles with no capital…squeezing time from a rock to get us to the next month.

She does not want me, but she wants my work. She wants me in every way except in social media. Cook her dinner…sure. Travel to a business meeting and have sex in the hotel after dinner, cool we know each other’s bodies.  But, Social media is the great dividing line. She has another life that I am not part of…that she does not want to share with me anymore.

I want to quit. I want to leave everything. I want to sign a contract absolving me of any liability in exchange for my shares. I want to #jointheForeignlegion, #destroymypreviousself, #startwithanewname.

But I can’t, because, I am an entrepreneur and we work till failure, or exit. This company has turned a corner. This company will be a prime mid-market acquisition target in 10 months, no….18 months. This company will bring her back to me.

This company will probably #fail like the rest because the love failed.

My advice to every single entrepreneur in the world: #neverstartacompanywiththewomanyoulove.


  • I think you’re a little bit crazy to be honest. You seem waaay to obsessed with what she’s doing on social media even though you admit that you work together and sleep together, so it’s not like it matters what she does on Instagram and Facebook. You’re right that it was a mistake to start a company with a girlfriend. But, now it’s too late to turn back on that.

    You need to stop being so obsessed with winning her back and worry about your company. In the end, you can always find another woman, but you can’t easily create a new company that’s successful. It’s harder to make money than to find love.

  • I followed the suit and joined my significant other in starting his dream business. Things are falling apart, personally, so much so that I don’t want to be in love anymore. Work wise it has never been better, the company is growing, everything is working out well, but it has come with a cost, which I have paid.

  • When you are sad, remind yourself a simple sentence :

    this moment will passes with time.

    When you are happy, remind yourself a simple sentence :

    this moment will passes with time.

    Post again in this post in 3 months, then in 6, then in 12, and you will read and smile about what is making you crying today.

    Just wait, and the time do the rest for you.

  • “She wants me in every way except in social media. Cook her dinner…sure. Travel to a business meeting and have sex in the hotel after dinner, cool we know each other’s bodies. But, Social media is the great dividing line.”

    Sorry mate but this part makes you sound like an insane person. So she sleeps with you and you spend time together but the relationship is a disaster because you can’t see her Instagram? Didn’t you say that you HATE using instagram? Have you ever actually asked her about any of this?

  • Company owners are tough as steel.

    Stop letting her control you.

    She flipped a switch on you and you’re freaking out.

    Stop giving her the control !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

    You are a bad ass company owner.

    You’re tough as steel. Right ?

  • She found another man. She lives that new life on social media with him. She also love the company and don’t want to destroy it.

    Having sex with him proofs nothing but they know what they like.

    She loves another man. She might get back to you eventually. She might not.

    You can get over her by dating another woman. But you will never forget. At least that happened to me.

    Good luck mate.

    p.s. for all others…unless you really loved a woman, you cannot understand the position of such man.

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