update: I started a business with two coworkers and I’m doing all the work

by Alison Green on November 28, 2022

It’s the launch of “where are you now?” season at Ask a Manager! Every day from now until the end of the year, I’ll be running updates from people who had their letters here answered in the past.

We have so many updates this year that I’m going to be posting six to seven times a day for the next several weeks — so keep checking back throughout the entire day.

To kick us off…

Remember the letter-writer had started a business with two coworkers but was doing all the work herself? Here’s the update.

I have a good update to this letter!

I wrote in asking for a script on how to wrest control from my business partners, but you will probably remember me more for having a business without a bank account. Allison’s advice, and most of the commentariat, said to reconsider whether I wanted to be in business with these guys. One commenter asked me if I even was cut out to be a business owner. That hurt a little to read, but it really prompted a deep self-reflection where I realized that yes, I do want to run this business and I’m invested in it. (I also had a lot of people wondering WTF my job was. While I’m still not comfortable saying it because it’s very specific, I promise we were not screwing over any vendors or customers. The service we provide is subscription-based and people still received the service.)

So, right after my letter was posted I took action. I had this mindset of “we’re a small business, we have to do everything ourselves” but that isn’t always true. Clearly we’re not good at money so we need help with it! I set up a meeting with a bookkeeper to get us sorted out. I basically told her, “Look, here’s where we’re at, and if you don’t want to work with us, that’s okay.” She fortunately did want to work with us and has been so helpful! I pushed my cofounders to set a date to set up a bank account, and I’m so glad to report we do have a bank account now. I also had a budgeting session with our bookkeeper because frankly I had no idea what our financial situation looked like, and she reassured me that we are doing fine and while we’re on a tight budget, we are not on a shoestring, which was great to hear! I’ve since set up meetings with people who can help improve our business since our bookkeeper projected we could afford it, so that’s been exciting. I also let the guys know that I’m basically taking the lead on one of the projects, for which they expressed appreciation.

Recently, though, the tipping point was when James called me livid about Sam’s performance at one of the elements of our job. Essentially, Sam keeps taking on more tasks than he can realistically handle and refusing multiple offers for us to take over and help. This time, he let something slip that we’d paid a consultant to help us with, which felt like a gigantic waste of money. James raised all the same concerns of Sam’s performance that I’d been struggling with internally, and I could not believe that it wasn’t just me feeling this way! And I was really inspired by seeing James begin to take it more seriously than it seemed he had been all along. We had a come-to-Jesus meeting with Sam where we told him we would need to take the task away from him. He emphasized how much he wanted to do that specific task, so we took another job function away from him instead, one that he enjoyed less but felt compelled to do because he doesn’t want to disappoint us. We realized that Sam wants to feel important and not let anyone down, so we reminded him that it lets us down more for things not to get done. I felt that I was being kind of harsh with Sam: he’s obviously sensitive about his output and his perceived shortcomings compared to James and I, and as a result he takes on WAY more work than he can handle–and then doesn’t handle it. So we basically told him to stop doing that. It’s working out well so far: last week he delegated something to me! I think getting our act together really helped us get excited about this project again, and I’ve realized that I was being a little arrogant about the amount of work I do: we all do a lot of work and it does take each of us to make this happen.

Thanks to everyone who gave me the wake-up call I needed. Ultimately I really believe in the product we’re bringing and I want to be doing this. I hope this is a satisfying update! If I can give some advice to other entrepreneurs: don’t feel the need to do every single thing yourself, delegate when you can, communicate honestly and often with your business partners, and open the damn bank account before anything else.

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    1. Chauncy Gardener*

      I couldn’t agree more! I’ve been thinking about this OP and am so glad things are working out well

  2. jane's nemesis*

    We have so many updates this year that I’m going to be posting six to seven times a day for the next several weeks — so keep checking back throughout the entire day.

    I cackled in glee and ordered some popcorn to get me through the month!

  3. fine tipped pen aficionado*

    You love to see it! Update season is the best and I’m glad you had the difficult conversations, OP!

  4. Gingerblue*

    Aw, this is such a great update. “We tackled doing the hard things we’d been avoiding and everything was better than we thought”—yes, more of that please! Great job, LW!

    1. Gingerblue*

      …this has in all seriousness given me the juice to go start some tasks I’d been avoiding of my own.

    2. GammaGirl1908*

      Also, this really struck me: realized that I was being a little arrogant about the amount of work I do

      This is huge. Bigger projects and relationships than this have fallen apart because one person thinks “I’m doing SO MUCH” =/= “I’m doing everything.” You may indeed be carrying a massive load, but it’s critical not to underestimate the contributions of others when their load is massive, too.

  5. Just here for the scripts*

    Fabulous news—especially for us anxiety-based folks who always worry that the stuff that’s unseen is bad! Shows it’s not always bad news hiding under that rock!

  6. Alexander Graham Yell*

    What a great update! Kicking off update season on a high note, for sure. Well done, LW + co-owners, on figuring out a way to move forward (and great news about the budget!).

  7. Momma+Bear*

    This is a great update. I’m glad that everything is improving and the business is building. Working with friends can be hard.

  8. Introspective*

    It continuously amazes me how I see letters and think that a situation can’t be improved, or a coworker couldn’t possibly fix things, and then see things work out. It always reminds me to give people and tough situations the benefit of the doubt. So happy that this letter writer had been able to really turn things around.

  9. Talula+Does+the+Hula+From+Hawaii*

    “We have so many updates this year that I’m going to be posting six to seven times a day for the next several weeks”

    The most wonderful time of the year!

  10. Scandinavian Vacationer*

    YAY, updates! Really hoping for an update from the AgroTourism Farm, also a business working with friends.

  11. Anonymous When Admitting Deficits*

    OP, you really inspired me to deal with a similar situation and my life is a million times better for it. Thank you.

    1. OP*

      OP here: this makes me so unbelievably happy to hear. Thank you for telling me that. I am so glad I was able to inspire you in that way!! You’ve got this!

  12. lunchtime caller*

    What a fantastic update! Investing in back office support is definitely one of the (anecdotally) most critical factors I’ve observed in taking a small team of hard workers with really specific skillsets and multiplying their impact exponentially. Pouring your energy into a task like bookkeeping that you’re not particularly good at or trained in takes both time and mental energy; meanwhile being able to put those things to work in other areas of the business hopefully means that now you can make even more money to more than offset that cost!

    1. Lenora Rose*

      It’s the business version of Captain Awkward’s “Sometimes the cheapest way to pay for a thing is with money” advice.

    2. Where’s the Orchestra?*

      But it’s also so true – most people aren’t professional everythings. They can be enormous value in hiring professional services for things you don’t know how to do – because then you can spend more time and energy on the things you are the Pro at.

    3. JustaTech*

      If there’s one thing I learned from watching my in-laws get their small business ready to sell, it’s that a good bookkeeper is worth their weight in diamonds, and it’s not a task that should be delegated to whoever didn’t avoid it fast enough.

  13. Chilipepper Attitude*

    OMG, I forgot about update season! I am so very happy today!

    Congrats to OP on the changes! Very inspiring!

  14. Clobberin' Time*

    Great news! But LW, please be aware that you’re not being “harsh” with Sam. Don’t fall into the trap of putting Sam’s need to avoid feeling bad over insisting that he does what he says he’s going to do (and not just the “fun” stuff, either).

  15. HugeTractsofLand*

    Getting a bookkeeper was such a smart idea! I’m so glad that you delegated and feel less burnt out now. I think having an external staff member has the unexpected benefit of making everyone else feel a bit more official, too. Good luck with the business!

  16. sdog*

    This is a good update, but I don’t know, something seems lacking still. Maybe it’s the fact that OP and James still seem to be catering to Sam’s feelings. Isn’t OP taking charge of finances (by hiring the bookkeeper, etc.) exactly what she’d wanted to avoid? I think it’s an awesome move, but it basically took the task away from Sam and let him keep shirking that responsibility. Of course, it’s totally fine for each of the three partners to re-evaluate their strengths and re-allocate tasks among themselves, but I’m still not a 100% clear that everyone’s roles are more equal now. I think that job description proposed in the initial letter would still be a good idea, and it sounds like the other partners may be more receptive to that now.

    1. Zorak*

      I somewhat agree; I think in this type of situation there’s a balance that needs to be struck between “You have these feelings and impulses so we’ll try to arrange things so as not to aggravate your insecurities” and “You at some point need to get over it, friend, this is a business.” Beware that taking duties away from Sam because he behaves (slightly) irrationally in regards to them doesn’t become a crutch / doesn’t unbalance the workload.

      That said, great update! I’m happy that things are looking up for you!

      1. GammaGirl1908*

        +1. Sam doesn’t 100% love this necessary thing and has a tantrum =/= Sam gets to never go near the thing.

        Sure, do the best you can to give everyone as many tasks that fall in their wheelhouse as you can, but if it has to get done and Sam is the one available to do it, Sam needs to suck it up. We all have to do things we don’t 100% love sometimes.

        1. rebelwithmouseyhair*

          Well no. I mean, if you want our business to fail, put me in charge of bookkeeping. I just can’t. It gives me a headache. For my own little business, I chose the system with the least accounting stuff, and I’ve learned to do it as it comes up rather than letting it pile up at the end of the month, so that it’s spread out and I never need to spend more than an hour on it. And it’s only me that’s affected. For a business with partners, I will avoid accounts at all costs.
          People go into their own business to be able to do what they like.
          Of course there’s always stuff you don’t like, but you can delegate or outsource. If it turns out that Sam is dealing with much less than OP, they can assess whether OP should get a larger share of profits, or salary, or maybe reassign some of OP’s stuff to Sam. The possibilities are endless.

      2. rebelwithmouseyhair*

        Since OP also reevaluated the proportion of work she is contributing, I don’t think that’s something to worry about. All partners seem to be working on stuff.

    2. Snow Globe*

      I agree. I think there has been good progress since the first letter, and I can see why the LW is feeling better about things. But it still sounds like the LW is still doing far more work than the partners, while they are all being paid equally.

    3. HufferWare*

      I agree, but also think a lot of my concerns come from my reticence to hand-hold. To me, I’d be much more concerned that one of the 3 heads of the company I invested in was taking on tasks to “feel important” but did not actually follow through on the task and doing that repeatedly despite my cohorts asking me not to. That his ego was so front and center despite his wife, who is not part of the company, having to step in and urge him to open a bank account, and remains so front and center that his cohorts have to regularly give him pep talks so he’ll actually do the work he said he would, takes me aback personally. But that’s my level of tolerance for that kind of stuff and the priority OP had for the personal relationships with Sam and James are also to be considered. So yeah, happy for OP that things are working out in a way they are comfortable with, and happy for myself to not be in a similar situation LOL

      1. Zorak*

        Agree, for Sam step 1 was identifying his hangups, and step 2 has to be disengaging from them so they’re not holding the reins.

    4. Person from the Resume*

      I agree. I was very surprised to see all the “this is a great update” comments.

      It’s better, but the problem remains that Sam is dropping things and they’re trying to manage Sam’s feelings about tasks.

      A fly in the ointment is that they are all founders and equal, but it sounds like Sam needed/needs some management and supervision to perform well. This could continue to be a problem.

    5. Clobberin' Time*

      The OP doesn’t want to confront her friend Sam and isn’t going to, so I guess this is the best it’s going to get?

    6. lyngend (canada)*

      I think the difference is that this is 3 people who know each other and are of equal ranks. And we don’t know the whole conversation. Sometimes things take steps in order to work.
      And I’ve heard of more then one person whose said “if my employer takes x task away from me I’m leaving” or similar things. I know I’ve had things like that.
      To me this is a better balance. They took the task the co-owner didn’t actually want to do, but felt compelled to, and left what he did want to, and would have more commitment to.
      This opens the door to more open and honest communication between everyone

  17. Abogado+Avocado*

    This is a wonderful update! OP, I suspect you’ll inspire other entrepreneurs who read this site and who may be in the same situation you were in. Many thanks for letting us know how it all worked out and best of luck as your business goes forward.

  18. Lilo*

    Getting the bookkeeper was a good idea. If you haven’t already I highly suggest meeting with an attorney and forming an appropriate business entity.

  19. Artemesia*

    FWIW You don’t have a feel fr the financial side of the business and now have all that resting on your hired accountant. She may be the world’s most ethical person, but I personally know of three businesses or non-profits that were embezzled from because they rested their financial management on one ‘trusted’ person. One was a ‘best friend’ who worked in the small business. You need financial controls that routinely assure that more than one person is on top of the cash flow/financials. People who didn’t even have a bank account and now rest it all on one hired hand are VERY vulnerable to financial abuses.

    1. GammaGirl1908*

      Ha, I saw some show about stars of the 80s, and some two-hit wonder musical group was on. Their advice to others was: get yourself a good accountant. Then get a good lawyer to watch the accountant … and get a second lawyer to watch the first lawyer.

  20. GarlicMicrowaver*

    Nice for now, but does this fix any of the core issues? OP is simply appeasing Sam and tip-toeing around his feelings, IMO. Every major step, also, seems to be the OPs idea. Weight is not equal and OP is assuming control (e.g. bookkeeping decision) to affect change.

    1. Willis*

      This! Getting a bank account and a bookkeeper is progress but the company still needs someone that understands the financial component and some form of operating or membership agreement. What happens when one of these guys flakes again? If you need to kick someone out, do you have a formal way to do that? If not, get an attorney who can help you set up an agreement ASAP.

    2. ferrina*

      Yes, it sounds like it’s going in the right direction, but more issues will come up. I’m hoping LW and James are on the same page now- it sounds like they weren’t talking as much as needed. Sometimes they just need to break the ice.
      But I’m more worried about Sam. What happens next time he takes on too much? Will he continue to be honest about what is too much, or will he hide that next time he’s feeling insecure and thinks he should do more? Sam’s issues sound like they may be pretty deep-seated and something he needs to work through with a therapist, not something the LW or a big conversation can solve.

      Agree with Willis- LW should talk to a lawyer to set up agreements and protections going forward.

      1. sdog*

        Yes, I think this thread puts a finger on it better than I was able to articulate above. While I’m happy to hear that things have improved, there seem to be core issues that did not really get addressed. +1 for agreements and protections moving forward, as well as clear delineations of responsibility moving forward (that do not just get shifted just because someone doesn’t like them).

      2. Where’s the Orchestra?*

        Agreeing with this – you, James, and Sam need to have some hard conversations and set up a structure so that there is accountability for everyone when and if a ball drops somewhere.

      3. Kevin Sours*

        The best time to talk to a lawyer about this is two and a half years ago. The second best time is now.

  21. Brain the Brian*

    I’m a bit concerned that it took a “come to Jesus” meeting to simply redistribute one task. But… yes, I suppose this is overall a positive update. Good luck, OP.

  23. Lacey*

    I’m so glad things are working out for you, OP! I did not think this was the update we’d be getting, but it’s wonderful to see that you all were able to turn things around.

  24. Kevin Sours*

    I don’t know if you guys had a formal partnership agreement drawn up covering what contributions are expected from the partners, how it’s determined if they’re being met, and what happens if they aren’t. And just what happens someone leaves. But you need one.

    Think if that conversation with Sam had gone badly and he refused to change anything what would you legal options have been to deal with it? Do you even know?

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