Entrepreneurs share their co-founder horror stories

by | Nov 20, 2020 | Blog

Christina Kaye

Christina Kaye

Founder/CEO of Write Your Best Book

Last year, when I first started brainstorming my business, I thought having a partner would be ideal. We could share the responsibilities and we could split the investments required to run a successful business. Less than a month after launching, I started feeling like I was pulling all the weight. I was traveling to conventions and expos, I was working with all the vendors, I was doing all the marketing, and most importantly, I was the only one seeking and communicating with potential new clients. I was waking up every morning at 6 am and not getting to bed any earlier than 2 am each night. I was losing weight, my hair was coming out, I was exhausted, and I was running on fumes. This business was my brainchild, and I was not about to let it fail because my partner refused to carry their share of the load, so I made the ultimate decision to terminate our partnership agreement. Eventually I relaunched the business under a new name, and business is booming! Write Your Best Book

Shawn Cannon

Shawn Cannon

CEO of Auntee B Naturals

I realized he was a bad fit when his insecure and jealous of every decision I made and was insulted when I didn’t implement his ideas. His ideas were never practical. When we launched our Kickstarter, he wanted to include a $40,000 pledge. When we asked the characters in the game to be a darker tone, he would not “bend the knee” to social justice warriors. And when he wanted to cancel the Kickstarter after we raised over $90,000 in two days because we didn’t hit $1,000,000 in the first day, I knew I had to walk away. And that day came when he demanded I beg for his forgiveness when we didn’t hit a million on the first day. Auntee B Naturals

Helene Berkowitz

Helene Berkowitz

CEO of ReceetMe

After being in business together for nearly a year, signs began to emerge that my co-founder was not as good a fit as I had thought. Although he was initially on board with my vision, when we would work on product design, he would often comment that we should do things the same way our competitors do it and not reinvent the wheel. But that wasn’t how I wanted the product to work – I wanted other functions, an entirely different UX, and different goals. Doing things differently was kind of the point. We had several meetings with potential partners and investors which he simply did not show up to, leaving me in the lurch. This behavior gave the impression that as founders, we weren’t taking things seriously and it caused some embarrassment. Although my previous co-founder had the skills to develop the product and oversee all technical aspects of the company, it became clear to me that I could not rely on him to co-run the company with me, not in the way 2 founders must rely on each other to grow and succeed. ReceetMe

Michael Coles

Michael Coles

Founder of ChooseYourReader

I realized my Co-Founder was not a good fit when we needed direction in technology and creating an effective internal business process and those tasks were going to fall to me if we did not invest significant cash to hire someone experienced in that area.
  1. If you outsource technology find a partner that has a business model based on your success

  2. You always need more cash than you budget so over-estimate and then add 20%

  3. Create job descriptions within your company as if you were hiring, then review the founding team’s resumes for matching skills. If a skill is missing you will need to hire someone to fill that role soon.
The Dog Tale

PJ Taei

PJ Taei

President / Co-Founder of Uscreen

Overall, Slack is a great tool that’s allowed us to grow and communicate with our 60+ plus team members from all across the world. As a remote-first company, even before COVID-19, it’s also enabled us to deliver a fantastic experience for our customers. The big downside with this ease and instant communication is that Slack can be hugely disruptive to people’s day to day work and business operations. This ease, coupled with the number of non-work-related channels and conversations that can appear from time to time, means you can spend more time chatting, going back on forward on conversations then completing the objectives for the day. We decided early on in our growth that with each new hire, we deliver in-depth training on how to use the platform efficiently and that our team think before they write so that they are specific and precise with their communications. Moreover, because it’s not possible to talk over video all the time, text chat can also get misinterpreted. By taking that extra time and consideration for each other, we are more respectful of everyone’s objectives and that we always deliver what is needed to help our customers succeed. Uscreen

Phil Crippen

Phil Crippen

CEO of John Adams IT

  • Their cheesy little icons like their mascot and the hand wave.
  • Every time I log into a new channel, it goes through the same tired old ‘Welcome to slack’ stupidity. How easy would it be to detect that I’ve seen it 20 times and I don’t want to see it again?
  • I have to re-enter a username and password for each slack channel I join.
  • It doesn’t interface well with LastPass and causes me to manually enter every new channel into LastPass.
  • Free channels delete your messages after 10k.
  • Their search sucks, so it’s hard to find important things.
  • Every channel gets cluttered up with junk, making it useless.
  • Once you have more than one channel, it becomes a big pain to login to all the different channels and checks them.
  • It’s really not much better than a Google hangout. In fact, it’s worse because of all the different user names/passwords you have to keep track of/keep synced, the poor search capabilities, and the loss of information for free channels.
  • John Adams IT

David Meltzer

David Meltzer

CEO of East Insurance Group

With Slack, storage is a big challenge. Although all platforms have to make some revenue, of course, the storage for the free tier is just 10,000 texts. When you have a squad of five or higher, it’s going to happen in no time. History will not be preserved, and all previous communications will be stored or erased. The other day, I wanted to see some of the first messages we sent to Slack about a startup that I’m working with, and it was all gone. Messages are the most irritating part about this experience. When you are out of room, attempt to upload, you will get pinged back about the room cap being reached. This is frustrating, so you would certainly be distracted by the message and leave a good red message icon on your Slack app. East Insurance Group

Mike Sadowski

Mike Sadowski

CEO of Brand24

The thing I hate about Slack the most is that people writing to you on there expect you to answer immediately. There is not much thought given to your time and that you may be busy at the moment. If you don’t reply, they will notify you until you finally do. It’s annoying to find out that when you log into Slack, you’ve been alerted a hundred times just because you were doing something else at the moment. Another thing is when you have a large work environment on Slack it’s getting hard to keep up with all the rooms, messages and channels. As the messages whizz by, I get nervous not to miss anything important. Don’t get me wrong; Slack is a great communicator if you use it correctly, although there is a lot of potential for misuse. Brand24

David Wain-Heapy

David Wain-Heapy

CEO of Prodigi

The thing I hate about Slack is the reason why I chose it for our business – a communication tool used for fast replies. The big negative of Slack is the interruption as It sets an expectation of immediate answers that you don’t have with email. This can be really distractive, but it can be avoided if you turn off the notifications during your focus time. Prodigi

John Sickmeyer

John Sickmeyer

CEO of Postali

I don’t like the search functionality. One of the primary selling points used to convert free Slack users to paid subscribers is unlimited search. But in reality, the search function is very bad and both the UI and the underlying code need a major overhaul. I can’t think of a single time using it, where I am able to find what I am looking for. Are you finding what you need? With Slack, it is rare. You have to just keep trying different searches and hope you can get what you need, but oftentimes, you just can’t. Postali

Rahul Vij

Rahul Vij

CEO of WebSpero Solutions

  • It has a boring, dull appearance that a classic chatroom had.

  • All notifications are treated with the same urgency.

  • Slack doesn’t decrease the number of platforms you use for communication and information transfer.
  • WebSpero Solutions

Matt Bowman

Matt Bowman

President of Thrive Agency

Slack is best as a replacement for email, but not a complement to it! Slack is also pretty non-hierarchical in its implementation, and more hierarchically-organized or politically-intense firms or departments may show a strong dislike of it. Lastly, one academic organization I know evaluated slack: they needed to retain all their data but have no resources to upgrade to the paid versions (which you need to do after 10,000 messages to search previous ones!) Now, a Slack competitor offers free membership for academic organizations, and they switched to that rival. Thrive Agency

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On the podcast, Sean talks with entrepreneurs about the reality of their struggle to succeed, as well as answering questions from the community, and sharing nuggets of wisdom from his own life.


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Sean Weisbrot

Sean Weisbrot

Sean is an entrepreneur, investor, and advisor based in SE Asia for over 12 years. He is passionate about Psychology and helping others improve themselves.

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