December 1, 2018

29 Lessons I've Learned Bootstrapping In 2018

  1. Bootstrapping is about launching products on existing markets (so the idea is already validated), niche it down ideally to 1000 customers worldwide (1000 x $50/m, ±$500k/y), then niche it down again to reach and segment target audience easily, establish better execution and UX as a main competitive advantage (and to attract competitors refugees) and find your flywheel via semi-automated marketing/content creation (to achieve the lowest possible CPA). Don't create new markets, don't chase innovative ideas. Prefer optimization over innovation.

  2. Bootstrapping (and entrepreneurship) is a career. Don't expect quick results. Stack bricks one by one. Stairstep rather than jump. Run a marathon, not a sprint. Do back-envelop estimations and plan to spend on one project three years rather than three months. Read/Listen Rob Walling today.

  3. You don't have a business if you don't have profit. Be always profit first. Pay yourself first, then pay your creditors.

  4. Start marketing before coding.

  5. Start write/collect your content before marketing.

  6. Recognize and write down your product value metric. Read/Listen Patric Campbell today.

  7. Niche down, then niche down again.

  8. On-boarding should guide a user on how to get value from the product in less than 30 seconds and nothing else.

  9. Eliminate as much friction as possible along the user-to-customer journey in your product. In extreme show your offer to a user right after on-boarding.

  10. Avoid trials - they prolong user's journey to your offer, put time constraints to a potential customer and force them to focus on your product (that's bad as we all have ADHD). Prefer freemium to trials where you could restrict the user's ability to get more value from the product keeping it just on a bare minimum. The user should stumble upon the product's "value metric" every session and suffer by not able to have it all. If you concerned of support burden for the free tier make registration private and rechannel the rest of the traffic to a waiting list.

  11. Always collect emails. On an early stage prefer email collection to conversion. You have better chances to reactivate user with email than reactivate a lost visitor without one.

  12. Always be testing. There is always a better version of your product (and more profit) waiting for you in just a couple of commits.

  13. Any hype is good for your content/marketing strategy. People love controversy. Consider: "10 reasons why PayPal is better than Stripe for your info products checkout page" or "How bootstrapping ruined my life. Drained and divorced with $150k in debt".

  14. Sell on value rather than on price: products with product-market-fit either making money, saving money or saving your time.

  15. Charge more, it's the easiest and most controllable way to immediately increase your revenue. Read/listen Patric McKenzie today.

  16. Charge more, reconsider (rise) your pricing monthly while something bad won't happen (you'll see it as significant conversion drop/churn rate increase). Read/listen Jason Cohen today.

  17. Optimize conversion. It's the second most important way to increase your revenue after pricing. Fix your leaked bucket before double down on marketing. Squeeze any penny from the current product state before moving forward and build more features.

  18. Invest your time into 1. conversion optimization 2. execution (UX) 3. marketing rather than new features.

  19. Don't ship features. If you are developing new features stop today and think which one to remove without losing your UVP.

  20. A new feature in your product should always serve a new segment of your potential customers. Build it just after you already optimized the previous version of your MVP. If it's not the case you probably don't have an MVP.

  21. Be able to dynamically change pricing to your service in seconds (not days) through your admin panel (or DB).

  22. Make sure your bounce back rate is low, otherwise you attract the wrong audience.

  23. Bootstrappers don't build products. They build marketing/conversion systems around MVPs, optimize them and replicate what works.

  24. Choose products that could be scaled horizontally to serve similar audiences. This way you could replicate the system and product relatively easy, target a different segment of customers and multiply your revenue.

  25. Build technical platforms to reuse them to multiply success.

  26. Use boring technologies, that decreasing the cost of bootstrapping and code maintenance. Hack around for fun, not for profit.

  27. Don't forget to use Black Fridays/ XMas sales to close more deals from your mailing list.

  28. Implement promo codes and offer a small discount to everyone in your mailing list as a part of your drip campaign.

  29. Use "Unlock" CTA rather than "Upgrade" CTA. People naturally love to unlock doors (paywalls).

  1. 7

    I don't really like the phrasing of number 23, it makes Bootstrappers sound like scammers that don't care about what they make or don't care about the audience bit instead they only care about money. Most of the other points are really good

    1. 3

      LOL. It doesn't make bootstrappers sound like scammers. It's a legitimate angle of perceiving what we do. How do pull from that wisdom that the maker doesn't care about the audience? That they only care about money? The culmination of shipping a product is evidence that they care...and rightfully be rewarded with money.

      1. 0

        Because it literally says that Bootstrappers don't build products. For me the products and the value they bring to the audience are the most important aspect of the maker/bootstrapper community. (Just my opinion)

        1. 1

          I don't think you understand the nuances of metaphor.

          There is the product...and there is the process. Both of which are being referenced in #23. He is negating the product and highlighting the process.

          1. 0

            He literally says "Bootstrappers don't build products"

            1. 2

              He is negating the product and highlighting the process.

              He is sharing with you another way to perceive what you are spending your time on. You are taking what he says literally when he is using a metaphor.

              1. 1

                Let's just leave it here because we are both 'ot seeing each others point

                1. 1

                  You're taking #23 as offensive because you're mis-interpreting what he's trying to share with you...because you are parsing it literally rather than metaphorically. That's the point at where you throw an error.

                  Jeroen doesn't build Blockchains. He builds immutable ledgers around MVPs, optimize them and replicate what works.

                  1. 1

                    I see what you mean but my point that "marketing/conversion systems around MVP" the phrasing here still sounds sleezy and like the author doesn't care for his/her audience still holds true it's all about perspective and perception

                    1. 1

                      @hack3r I guess we hit the maximum of replies so I will have to reply at my own comment. I would like to say that we have different reasons to built products and that's fine. I built stuff for fun without the need to gain users or money from it. I built for the sake of the product, not for the sake of wealth and fame. We just have different opinions about this and that is alright people have different opinions. We don't all have to do things the same way. That's why it's an opinion, have I mentioned it is an opinion and you don't have to agree with it in any way because it is an opinion. Maybe my opinion and reason for building products will change in the future but as of now this is my opinion on the matter.

                    2. 1

                      "marketing/conversion systems around MVP" the phrasing here still sounds sleezy

                      There is nothing sleezy-sounding about using "marketing/conversion systems".

                      That's exactly what the mechanism is called within the context of gaining users. One cannot glean any knowledge of sleeze towards an audience by simply reading that combination of words. Those words are very accurate in their description.

                      Just out of curiosity, how would you edit #23 in order for it to be proper?

  2. 4

    Great post! Significantly more valuable than all the spam this site gets bombarded with daily.

    #23 should be a damn religion.

  3. 3

    No. 4 is extremely crucial. Don’t build until you validate the market.

  4. 3

    This is a really great list, some brilliant points on it, k love 1/7 finding niches and getting deeper into them, something I've been really working to get better at.

    8/9/17 getting users up and running and show them the value.

    15/16/21 love this one, I hadn't thought about the changing price quick and easy in the admin side, that might be why so many of us never really increase our prices, I know I've done that. Think I'll give that a try next time and see what happens.

    Thanks for the great list Alex and I've bookmarked it, a lot of things to think about.

  5. 2

    Good points!

  6. 2

    really useful! Good job :)


  7. 2

    What a great list!

    I wish I knew all these before starting...

    Thank you for sharing such great value :)

  8. 2

    Bookmarked and shared 👍

    Thanks for this list. Really helpful advises. I guess you've collected this list for yourself first? 🤓

  9. 2

    Choose products that could be scaled horizontally to serve similar audiences. This way you could replicate the system and product relatively easy, target a different segment of customers and multiply your revenue.

    I think this shows a lot of clarity. However, it is hard to obtain. If you narrowed down your market as you described earlier, you could have already identified other valuable segments for your horizontal scaling. Do you have any examples on this?

    1. 2

      Yes, I have a product that called FullStack.Cafe that helps Full Stack devs to nail tech interviews. Rather then continue to add topics regarding .Net stack on it I've branched it to a separate product called DotNet.Cafe. So my niches: devs who nervous about tech interviews, subniches/segments: full stack devs, .net devs and technically it's the same CMS with minor copy modifications.

  10. 2

    Awesome post, Alex! Thanks for providing such great value

  11. 2

    Thanks for this. Great post.

  12. 1

    Great write-up, thanks. Can you prove 29, Unlock vs. Upgrade with a case study or some sort of A/B testing results?

  13. 1

    thanks for sharing

  14. 1

    @aershov I referenced your post in my article on landing page user testing.. would love to hear your two cents..

  15. 1

    @aershov Loved the last point about "Unlock" CTA.. !

  16. 1

    I got to about 13 and stopped. Here’s a couple things I’ve learned from launching funded and bootstrapped companies over the past 7 years or so

    1. Everyone’s journey is unique so don’t assume what worked for someone else will work for you

    2. Every company is unique. So something that worked in company X (like trials) may not work in company Y.

  17. 1

    #29 so true!

  18. 1

    I strongly disagree with #10 when it comes to B2B. Free users are expensive and will likely take up the majority of your support efforts. A boostrapper will prioritize customers which provide revenue, not give away your product for free to the majority.

    1. 1

      Me as well...and with a few others like 18 and 19. For some markets and especially when you are bootstrapped freemium doesn't work.

      There is a reason so many companies ditched freemium for free trials and most companies still using free trials.

    2. 1

      Good point but I think it depends more on how you provide (and restrict) your value metric. Have a look at, they have a free plan and restrict service usage based on your site traffic (up to 2000 monthly visits for free). Using that model they could engage more potential customers who inevitably will stumble upon free tier restrictions. I guess their conversion rate for "activated" users should be 10-15% (btw I one of them). Same for Mailchimp and Drip. Also, if you have a free tier you could make the registration private (to handle throughput and support as you said) and rechannel the rest of traffic to a waiting list. (see for example).

  19. 1

    Oh my god... I think I need a printer right now.

  20. 1

    In #12, what do you mean by testing?

    1. 1

      A/B test your pricing, CTA, copy, and images. As a part of conversion optimization you could create two versions of pricing page (A/B) and pull prices and copy back from DB for eather test.

  21. 1

    This list is great. Love No.7,9,12,23. Thanks Alex! Bookmarked this post!

  22. -2

    This comment has been voted down. Click to show.

  23. 1

    This comment was deleted 3 months ago.