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    Wednesday, September 8, 2021

    Startups Co-Founder/CTO seven years in. Burnt-out and thinking about leaving, but terrified of the process/impact

    Startups Co-Founder/CTO seven years in. Burnt-out and thinking about leaving, but terrified of the process/impact


    Co-Founder/CTO seven years in. Burnt-out and thinking about leaving, but terrified of the process/impact

    Posted: 07 Sep 2021 06:54 PM PDT

    tl;dr: I've been co-founder/CTO at my startup for seven years and I just feel burnt-out, under-compensated, and overwhelmed, and my personal life has really been suffering (I've felt like this for years). I'm ready to move on, but I'm terrified of the process. Finding the right person to replace me and transitioning all the knowledge (most of which is only in my head) feels like an impossible task. Additionally, I'm concerned about the impact to company morale and how this might affect investor sentiment. I'm looking for stories/advice from anyone who has gone through something similar.

    Full Post

    I've been co-founder/CTO at my startup for seven years. Over the past few years I've started to realize that my personal life has suffered immensely from the stress, time, and energy involved with my work. Additionally, I don't think I am an effective CTO/manager (no previous experience) nor am I interested in it. I find it extremely difficult to delegate/hire and I have an uncontrollable desire to know the details of every system/process, so I end up doing a ton of work myself. I found this article very relevant, especially #1. This was an exciting opportunity when I first started, but now it's just ballooned out of control and I need to pull the ripcord.

    I'm also not super excited about the product/industry anymore, and I think my engineering skills could benefit greatly from working in an established engineering team/environment, where I could learn from other engineers as well as be exposed to new and different problems, methodologies, and tech. I also think my overall output would be much greater in a position with more limited scope/responsibility; right now I am spread way too thin. I know there's a tradeoff, in that I could find myself bored with working on Widget #2534 forever, but I know that my current trajectory is just not sustainable. I could also make 2-4x my current salary, given how much demand there is for senior engineers (fwiw we have had 2 previous engineers leave for FAANG positions)

    I also think our company itself would be better served by someone with more experience in all the areas needed to scale a startup/team to the next level. I think our current tech/product has decent groundwork, but the skills necessary to scale and build things up feel totally different from doing the actual development, and it's just not the right fit for me. It really takes a special breed to lead and scale a startup and I just don't think I'm that person.

    So, I'm 99% sure that I need to let this go and move on to a position with less responsibility and stress so that I can focus on other parts of my life. However, given that the majority of our technology/architecture is only known by me (I am also the sole backend developer), combined with my co-founders being non-technical, the process of finding the right person to replace me seems like an enormous challenge. I don't have the first idea of how to approach this. Obviously I don't want to leave them holding the bag, but I also don't want to drag this out forever.

    There's also just a huge emotional hurdle to get over, in that this company has been my life/family for the past 7 years, and now I will be leaving them. It feels like breaking up with a long-term girlfriend, when there's no one specific reason (e.g. "you cheated on me"), but rather it's just "not the right fit".

    I will of course be having plenty of discussion with my co-founders (who I think will be shocked, but understanding) on how to approach this, but I'm curious to hear any stories/advice from anyone else out there who has gone through something similar. Some specific points/questions:

    • What should be my role in finding a replacement? Should I lead the process? Or should my co-founders/CEO lead, and I provide support?
    • Tips on finding the right replacement? Finding good engineers is hard enough, finding a good CTO sounds impossible, though I suppose it helps a lot that we already have an established product and user-base, and have investors waiting to give us more money
      • Also, given that my skills are more in line with a developer, rather than a CTO/manager, I'm unsure of how I/we should be evaluating candidates. I would think technical ability is less important compared to the ability to build an effective team, but I don't really know how to even evaluate the latter.
      • My co-founders are non-technical and we don't have any other senior engineers, so I imagine I will need to be highly involved in at least vetting technical ability
      • I also have a nagging thought that we just won't be able to find the right person, and the energy of the company will never be the same. But for my own sake, we have to try.
    • How long should I expect this process to take? I don't want to leave them holding the bag, and I have a (literal) vested interest in making sure we find the right person, but I also need to get out asap for the good of my mental health
      • How long to find the right person?
      • How long to handle the knowledge transfer?
    • How do we handle internal messaging?
      • The most straightforward would be to just let everyone know at the start, but this will be a huge hit to morale, so I'm trying to mitigate that as much as possible
      • An alternative approach could be to hire someone under a similar title (e.g. VPE), and then as the knowledge transfer finishes up, we announce that they will be replacing me. But there's always the possibility that some employees will hear about this early through the grapevine, which I imagine could be pretty damaging.
    • How do we handle messaging to current and potential investors?
      • This will be a major event/shift in our company and I don't want to spook investors and ruin our chances for raising more money
    • I imagine that even in the long-term I will need to provide some level of support/consulting, and I believe I could even continue in some sort of individual contributor position, but I don't want that to be a crutch that extends the company's dependence on me. How do I evaluate this?

    It's been extremely difficult to try to organize my thoughts for this post (as well as the initial email I'm writing to my co-founders) so apologies for the mess. It's crazy how surreal and jumbled my thoughts on this become when I try to write them out. I think there's just so much bottled up stress, regret, anxiety, and unanswered questions that my brain can't process it. So I guess I'm also looking for any moral/emotional support that will help me get through this.

    Any tips, anecdotes, advice, etc. is greatly appreciated.

    submitted by /u/DogsAreAnimals
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    Company is broke. Should I offer my boss a deal to cut my salary?

    Posted: 07 Sep 2021 03:57 AM PDT

    My boss recently announced that fundraising is not going well and we're nearly broke.

    I really believe in the business and I think we'll find a way to survive and thrive (get gap financing from previous investors, get back into growth mode after summer slump, get new round in a few months).

    So I'm thinking to offer a deal to the founders to help reduce costs now:

    • I take a 20% to 40% salary cut now, for the next six month. I have enough savings to afford that.
    • In exchange, I get a proportional raise in six month, plus some extra equity.

    So for example if my current salary is $1000/month, I offer to reduce it to $800, and in six months raise it to $1200.

    I see that such an arrangement could create incentives for my boss to lay me off or reduce my salary eventually:

    • he could lay me off in six months, after having gotten six month of cheap labor out of me
    • after my pay raise, I would be a more expensive employee, so he could be looking for another cheaper hire
    • he could choose to not renew my contract, or to renew it at a lower salary

    So to prevent that, I would probably make a contract for this with a few clauses:

    • if I'm laid off before my salary loss can be made up, the remaining loss needs to be compensated
    • after the salary loss has been compensated (one year from now), my salary cannot go lower than a certain amount (say $1100 if we use the example above)

    Have you ever been in such a situation?

    Is this a deal that might be interesting for my boss?

    Are there drawbacks I'm not seeing?

    What other kind of deal could I offer?

    submitted by /u/sam__mann
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    Can I run my business anonymously?

    Posted: 07 Sep 2021 11:00 PM PDT

    I am planning to test my product by reaching out to potential clients at biotech industry. The problem is that I am employed by one of them and what if they ask me or find out later that I am working at a potentially competitor company. Even if I start communicating anonymously, at some point, I have to present the product or my employer may reach out as a client. I was even thinking about using a fake identity, would that be even legal? I don't have a co-founder or anybody else with the field and technical expertise to present the product. (The product is a consultation service and was not developed at my company through internal projects, and was completely separate from my duties) Any thoughts? Thanks in advance!

    submitted by /u/Educational_Sink_492
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    Customer Discovery Interviews

    Posted: 07 Sep 2021 03:41 PM PDT

    Hello Startup founders ! How do you find people Online to interview for customer discovery? People talk in comments etc but Its hard to convince people for an interview these days. I am talking to people in facebook groups etc . People also respond that they are facing a problem , but insist on talking mostly in comments etc rather than a zoom interview

    submitted by /u/imran371
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    Market Research

    Posted: 08 Sep 2021 02:13 AM PDT

    I'm rewriting my offer and repositioning my services in the branding space. As of now, I cater to multiple industries, but I want to niche down now. This is for all the founders and co-founders in the community.

    What are some of the business problems faced by startups regardless of being funded or bootstrapped?

    submitted by /u/Divya_Shah
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    Narrowing down target market

    Posted: 08 Sep 2021 01:59 AM PDT

    I'm the founder of a social habit builder app, and we are about to launch, but we are not sure who exactly should we target.

    Many people told us that "Young people living in the west" is a too broad range and we should narrow it down a lot. We have some ideas, but those are just that, we are not sure at all.

    How one does this? How did you guys do this?

    submitted by /u/Prince-Melden
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    How to think about founder/market fit?

    Posted: 07 Sep 2021 06:38 PM PDT

    It's a common advice to have founder/market fit (example) and choose a market that you're an expert in.

    I'm a PM at Google and my passion is in startups. I'd like to become a founder (now or in the future).

    I don't have any specific insight into a market in which I have founder/market fit. That's one of the reasons I'm leaning toward joining a seed/A startup as my next move (vs. founding w/o strong expertise).

    Any advice about how to account for specific markets when job searching? Should I be super focused on industry (e.g. Fintech, healthcare, AI)? Or can I focus on more broad categories (e.g. SaaS B2B)?

    Right now I'm focused on finding a great company regardless in SaaS B2B, but I'm worried that a few years from now I'll again lack expertise. The alternative is choose an industry first, but than I can be less picky on the company/stage.

    submitted by /u/bootstrapper-919
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    New product

    Posted: 07 Sep 2021 10:47 PM PDT

    Hi everyone, let's say I invented something new and easy to produce. I have a prototype, what do I have to do to place it on the market.

    I mean, what are the steps I have to follow if I start from a prototype and I want to see it on the shelf of a supermarket.

    Thanks

    submitted by /u/Cheap-Cheek8801
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    I've worked way more than my co-founders. How can things get fair again?

    Posted: 07 Sep 2021 12:59 PM PDT

    Hey guys,

    2.5 years ago a friend of mine and his university colleague had a great startup-idea and as I had just finished university and wanted a project to work on I said yes to starting a company with them. We decided on sharing equity equally (33% each).

    Both of them have a Bachelors in E-Commerce and I have a Bachelors in Human-Computer-Interaction. So my part was concept and building of the app, while they would do the marketing and business stuff. Obviously I didnt know what I had gotten myself into. I had never built a large scale mobile application, just got out of university and had to teach myself front/backend while doing all the UX stuff as well.

    In the past 2.5 years I've worked 40-60 hour weeks without salary while being financially supported by my parents (* since 4 months I am getting a 450€/month salary). The first 1.5 years I lived in a constant state of being overwhelmed with tasks, had burnout at least once and the relationship with my gf also suffered a lot as a result.

    I am the full IT department of our startup (which is a mobile application). I'm working 5 different jobs (frontend, backend, devops, UX and a bit of design). Both of them do a job that could be done by 1 person part-time (one of them even recently admitted that he thinks their job could be done more efficiently by 1 person).

    I always rationalized the extra work I did and said to myself: Once we get an investment, I can relax and my co-founders will have to work these long hours on marketing and business. Also without them I wouldn't even have this chance, because they came up with the original idea.

    In recent time, I've learned that once the investment comes, working less hours or taking a year off even, will not be an option for me as the person who built the whole app (unless we find an investor who is ok with that). Also I've contributed so many new ideas to the app and basically did all of the UX, so I think them having had the original idea doesn't matter as much anymore now.

    For more than a year now I feel that this is not fair anymore. And this feeling is killing me and taking away my motivation. I should also add that I don't really have any hard feelings for my co-founders. They aren't lazy or incompetent or unmotivated but there just wasn't as much work to do for them in the past years.

    So my question is: What would you guys do in my situation? I just want things to be fair again between us. I hate this situation but I don't want the company to suffer or die because of it.

    Thanks for your advice :)

    submitted by /u/Ficker8
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    What are the best payment processors for the gambling industry?

    Posted: 07 Sep 2021 11:21 AM PDT

    I hope this won't get deleted, probably will. Anyway, I'm looking into creating a startup in the gambling industry. My plan is to create a betting site somewhat like those casino apps, basically games with in-app purchases. So you cannot win real money or bet with real money, just can only bet with virtual money and do in-app-purchases. In my case it will be in-site purchases

    Does anyone know what are the best payment processors for this industry?

    submitted by /u/littlemancro
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    trouble signing on publishers as a new ad network

    Posted: 07 Sep 2021 05:38 PM PDT

    I started an ad network a couple weeks ago and I'm offering any publisher who chooses to sign up a 25% increase in the CPM theyre being payed + payment withdrawals every 7 days + better customer support since they can talk to the founders directly. I've been pushing this offer through cold outreach (emails and messages) but it doesnt seem to be getting a good response from publishers. Any idea why? also if you have other potential growth channels you think would work let me know.

    submitted by /u/TrifleUseful3102
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    Are there any places where you can get quick investment as an alternative to traditional 6 month fundraising?

    Posted: 07 Sep 2021 10:48 AM PDT

    I have a SaaS startup which just broke $20k monthly revs mark but we sadly won't upkeep it since we can't satisfy the huge demand we got for the product without further investment. My sales co-founder needs to constantly refuse orders. We can't increase our credit. As much as $70k would make us catch up to 80% of the demand and quickly make us reach something like $50k RMR which is absurd.

    Obviously makes me quite frustrated and I am guessing more people might have the same issue. The regular VC fundraising would take minimum 6 months of constant attention and building relationships with the VCs but as you can imagine time is money for us.

    So here comes the question is: are there any funds or places where you can find investors rapidly? Literally closing it in a week or a month? Or is there only traditional VC fundraising left?

    submitted by /u/roch_is_qubits
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