lessons from startupland

I'm currently trying to start my own company, it's a pretty basic B2B software company, I thought that it might be informative to make a thread on here that I could continuously update with lessons from startupland. The thread may provide insight into what it is like trying to do a bootstrapped startup, and might be helpful for anyone who is considering doing their own bootstrapped startup in the future

we launched about 1.5 weeks ago, I am focusing full time on sales (in extremely lucky position to be able to live with my parents and have low expenses so I can focus on this full time) and my cofounder is focusing part time on software development. we are 50/50 cofounders and have been working on the project together for a little over 2 months (I originally had the idea about 7 months ago though, and it took going through two other potential cofounders who didn't turn out to be a fit until I found the guy that I am working with now)

we haven't raised any VC money and don't intend to. we aren't seeking to scale this up into something massive, we are just trying to hit a single here

lessons from startupland:

  • finding a committed cofounder is hard af, especially if you are just an 'idea guy' like myself (probably swiped on 1500+ profiles on YC cofounder matching and didn't even end up finding a cofounder there).

    - what you have to understand is that these software developer guys, even young ones, are already making great money at their day job, I think that this makes them more risk averse compared to someone who isn't making great money in their day job and would thus be more willing to jump at an opportunity to work on something in their free time that could potentially make them more money, for whatever reason a lot of these guys that I talked to just seemed extremely risk averse. some of them wanted me to pre sell customers in order for them to come on board as the software developer. okay but then the project would have no risk. basically it felt like a lot of the people who I talked to weren't willing to work on something that might fail. some of them will probably never find a project to work on

    - if the software developer is good then they most likely have ideas for their own personal projects that they want to work on in their free time (whether they be money making projects or projects to work on for fun), they are already probably working on these projects before you even contact them about your idea

    - if the software developer is good then there are other projects that they could work on if they wanted to. you are competing against every other idea guy out there, some of those idea guys may have funding, they may have a more validated idea, they may have more experience in business/connections

  • you can't just be an 'idea guy'. with something like this everything is basically either the technical stuff (coding) or sales. you are going to need to get comfortable selling if you don't have technical skills - selling potential cofounders on working with you, selling potential customers on using your product, etc.

  • don't ignore red flags just because you are desperate to find someone to work on the project with you. when the developer has an illuminati sign in his Gmail profile picture, that probably should have been a sign that he wasn't the right guy. there were maybe red flags with the other potential cofounder too but I ignored them because I wanted to finish finding someone to work on the project with, well that just slowed me down by like a month

  • both you and everyone else are going to underestimate how long it will take to do everything, everything will take longer than you first thought that it was going to take, even when you think that you are accounting for everything taking longer than you first thought that it was going to take

  • I'm not sure if there is a cool lesson for this one but during the process of building out our product we discovered that Google is a scam job (in order to do what we had in mind in terms of integrations, part of the Google verification process would have required us to pay $15-75k for a third party security assessment that would only be valid for one year). we just dumbed down our product a bit as a workaround

  • test your website before you start selling it (first potential customer tried to buy $500 worth of credits on our site for $625 - the payment processing integration didn't work).

  • do not make changes that could potentially break the site at random times, especially if the random time is the morning of a demo (on demo with second potential customer, first demo, tried to log in to site and logging in didn't work while on the live demo, couldn't show the rest of the site and was pretty embarrassing, most likely lost the potential customer, happened because cofounder made random change to site earlier that morning instead of making changes on a schedule and then testing after).

Hope that some of this stuff helps or that people find it interesting. I would love to hear from/connect with other bootstrapped company founders, whether you are just starting out or further along than I am. Let me know if you guys have any questions.

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Comments (24)

May 16, 2022 - 8:23pm
famejranc, what's your opinion? Comment below:

when you think about it I basically bought myself a full cycle sales job with no base salary and relatively high upside/high time flexibility. the cool thing about our product/a basic software company in general though is that we should be able to scale it up without having to hire a bunch of employees.

May 17, 2022 - 7:36pm
famejranc, what's your opinion? Comment below:

another one. there are gonna be times when you feel like quitting. I was out with one of my buddies a while back and I told him that my company was dead, that I couldn't find anyone to work on the project with me and so the company was dead. my buddy basically told me to man up and not quit.

May 17, 2022 - 8:03pm
2rigged2fail, what's your opinion? Comment below:

cool. where'd you find you co founder? I've been looking for a developer but don't know where to start. 

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Most Helpful
May 18, 2022 - 2:11pm
Malta, what's your opinion? Comment below:

Hey there- I'll opine on some of these lessons too (especially since we've spoken about your idea). For full context, I'm a software engineer. I specialize in backend product engineering/ video streaming/ and SRE work.

  • Finding a motivated SWE is hard enough as is. Finding a good one that can spend their time is even harder. You have my number, feel free to text with questions. I'm happy to give quick responses, but I work quite a lot and am working on my own idea as well. I fall into your categories. I make $210k TC, plus I have a wife and try to study on my own. Even seeing friends I make calendar events in my phone to schedule it.
  • There's 3 essential ingredients to starting up a software based company (in no order, they're all crucial). Bringing 1 to the table is essential. Having an idea is part of product market fit, but there's a lot more to it as well.
    • Software Engineering
    • Product Market Fit
    • Sales
  • Red flags are similar here as to relationships. This is just a different type of relationship. I find that understanding people's reasons and motivations help me gain insight as to who they are as a person.

Some of your issues are part of why having a proper SDLC (software development lifecycle) is important. Here's a few pointers that might help you (and others, hence why I'm posting this publicly)

  • Have a Staging Environment and a Production Environment. You basically create an exact copy of your entire system that is not open to the public, so you can test stuff there. If your engineer pushes a breaking change.. well then they can fix it less frantically because you don't affect new customers.
  • Have "sprints". 2 week sprints are the standard, usually. Have an idea, estimate how complex the idea is (NOT time, just complexity) and then make progress on that idea. For a good developer, they should get simple features (ex. "A login page and full functionality") within 2 weeks if this is their full time thing. Some things may take 2+ sprints, smaller things (ex. "Change the background color here") should take far less time. It helps your organize your ideas, customer feedback, and overall technical improvements in a prioritization list and then you can execute on those. If it were me, I'd have one person focus on Sales and talking to customers about what they want, and one person building the thing. YMMV
  • If you need to push up big changes to Production (aka "prod" aka what your customers actually use), try to do it on off hours.
  • Yeah.. big tech is big for a reason. They'll rip your eyeballs out whenever they get a chance.

Let me know any questions (either text me or reply here). Happy to help out whenever I do get a few minutes of downtime here and there.

“The three most harmful addictions are heroin, carbohydrates, and a monthly salary.” - Nassim Taleb
  • 11
May 19, 2022 - 12:28am
Isaiah_53_5 💎🙌💎🙌💎, what's your opinion? Comment below:

Malta is the man.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee

  • 1
May 19, 2022 - 8:21am
GoingToBeAnMD, what's your opinion? Comment below:

The advice above isn't terrible, but you have to put better context around it to make it more effective:

  • You actually need 3 environments, Dev, Staging and Production and you're going to need to promote from one environment to the next to prevent the type of issue OP described. Using a cloud based service makes this type of stuff easier (you might need a good cloud guy too).
  • You will also need to implement automated testing in each of the environments to ensure regression testing and break-fix strategies. Your coder cofounder should already be familiar with this. Writing testing scripts may seem unnecessary at the beginning but you'll be grateful for them if your project grows to any significant size, I promise you that. 
  • You can't just call them "sprints" and feel like you're planning - c'mon son. You need to google "Agile Development" and start going down that rabbithole. That will give you a framework to implement so that you can better plan your time and future releases. It will also help keep your cofounder accountable to deadlines. it's likely that your cofounder already uses a flavor of Agile at work, so ask them which one they know best and work from there. Again, will seem unnecessary initially, but once you start seeing how it helps you meet releases and deploy products on time, you will be glad you did it. 
  • 6
May 19, 2022 - 10:45am
Malta, what's your opinion? Comment below:

I'd actually argue that your advice is more applicable at a later stage in their maturity process. To each their own, but here's my logic to your 3 points:

  • You don't need a Dev environment until you have enough engineers (both developers and QE) to need a stable environment. Assuming it's just one person creating everything, a dev environment is an unnecessary cost that won't reap benefits. AWS makes it easier to take snapshots of your DB and if you have pipelines it's not difficult to add additional environments as needed. Even feature environments, especially if things are architected using the serverless paradigm (Step functions, Dynamo/ Aurora, etc). 
  • Yep, completely agree on automation testing. It's just something I didn't mention above. Testing pyramid is huge, have tons of unit tests, some solid integration tests, and a good smoke suite.
  • Similar to my first point, someone adopting agile with only 1 engineer would likely actually impede on their cycles. It makes sense as you scale the team, but just a founder and cofounder don't likely need to be fully agile and have all of the scrum ceremonies. Again, YMMV and it might help. But if your developer knows what they're doing, I'd say a very relaxed version of Kanban is actually more effective.

Good points overall. I think getting a startup from 1 engineer to 3 engineers- you're absolutely correct on every point. 

“The three most harmful addictions are heroin, carbohydrates, and a monthly salary.” - Nassim Taleb
  • 7
May 19, 2022 - 2:25am
dapp43758, what's your opinion? Comment below:

As a technical person, any person that refer themselves as the "idea guy"; I'm going to assume that they are an idiot.

The technical people for the most part work

with other technical cofounders not wanna-be business bros who don't know anything. The reason why you're having a hard time finding a cofounder because they don't take a risk working someone who has no tangible skill. Lol

May 19, 2022 - 11:19am
famejranc, what's your opinion? Comment below:

Did you read the rest of my post. I was saying 'idea guy' in jest and said later in the post that you can't just be an 'idea guy'. Also have you ever tried to sell something? You could build a great product but without someone dedicated to selling it it will go nowhere. If you think sales is way easier from a time perspective than coding for having a successful project you are probably wrong, more time will be spent trying to sell this than was spent coding it. That doesn't mean that I don't value my co-founder, he brings a skill set to the table that I don't have and couldn't do the project without, and we are equal partners.

May 19, 2022 - 11:08pm
famejranc, what's your opinion? Comment below:

another lesson. it will probs be hard to even get meetings with people to sell your product to, in the beginning especially. it's been 2 weeks since I launched and I think I've only booked about 4 meetings so far off of lots of cold messages. I expect it to get easier once I figure out how to do the messaging better, for example I was getting no responses to any LinkedIn DMs that I was sending, and after changing up the messaging now I have got one meeting off of LinkedIn messaging and a couple other decent responses.

May 19, 2022 - 11:16pm
famejranc, what's your opinion? Comment below:

another lesson. ZoomInfo (where you can get people's phone numbers) is expensive af, I think I read $15k a year was their minimum plan. the only time that I wish I had VC money is so that I could afford to buy ZoomInfo or some other kind of data provider for phone numbers. honestly I feel a little bit fucked here because I'm trying to sell something to salespeople who I think are generally a bit more receptive to cold calls and less receptive to emails. if anyone has advice on this specific point I'd be open to thoughts.

May 22, 2022 - 5:52pm
m_1, what's your opinion? Comment below:

Regarding your difficulty with sales, here's a little trick I used for my first b2b heavy company. When you cold call, sound slightly irritated and ask for your target by their first name. 

"Hi yes mark please" in a short and fast way. 

The person picking up the phone will assume you know "mark". 

Was the ultimate way through gatekeepers.

If it does involve plenty of phone work - I'd recommend voicemail drops. They aren't very regulated and extremely cheap. Use someone like JustDeliverIt.

BTW there are cheaper services and ways of getting phone numbers. You can use a scraper and overseas labor to get leads for like $0.10 - $0.25.

May 22, 2022 - 7:04pm
Malta, what's your opinion? Comment below:

Love this- thanks for sharing. I'm building out my own healthcare focused SaaS and the sales aspect of it is a big unknown for me. I have experience cold calling people but in a different field, so these small tips are very useful.

“The three most harmful addictions are heroin, carbohydrates, and a monthly salary.” - Nassim Taleb
May 22, 2022 - 7:12pm
m_1, what's your opinion? Comment below:


Love this- thanks for sharing. I'm building out my own healthcare focused SaaS and the sales aspect of it is a big unknown for me. I have experience cold calling people but in a different field, so these small tips are very useful.

NP. It does get significantly easier but I absolutely hate  the $0 -> $10m rev stage because you are still trying to figure out if it's your shitty marketing or a bigger PMF issue. You spend a lot of time learning -> trying new channels -> attempting to scale them. Have done it a few times now and will never do it again lol :)

Plus you have no data...that's really the hard part. Once at scale you can do something like throw $ into a lift test to see if a channel is feasible on say...paid media...but can't do it at subscale.

May 22, 2022 - 7:57pm
famejranc, what's your opinion? Comment below:

thanks for the advice. it's easy to find emails so I have a list of contacts/emails for about 400 companies so far. if I could actually reliably outsource the finding the mobile phone numbers of those 400 people for $0.10 - $0.25 then that would be a good move so I might look into doing that, I assume Upwork or something is where you can find someone to do that. I have two big meetings set up for Tues so I am excited about that, one with this 80 person company and another with this 600 person company.

May 22, 2022 - 8:13pm
m_1, what's your opinion? Comment below:

Ex cumque molestiae iusto ipsa et dicta corporis. In deleniti eveniet nulla qui illum asperiores. Minima et repellat quia. Quam et asperiores ad est provident sint tempore modi. Id rerum eos nam non aut. Rerum eaque pariatur veritatis qui cum quo nobis. Laudantium aut eligendi expedita alias unde et.

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