Kalo Yankulov

My startup made $2M before I sold it. Here are 16 things I learned

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I launched my SaaS company, Encharge, in 2019 with less than $1,000 in my account, no funding, no network, no audience, and no accelerators. It generated $2 million before we sold it. Here are 17 things I learned from it.

1. Startups are a last-man-standing game.

The one to win is not the fastest, smartest, or best. It's the most persistent and resilient.

2. If someone tells you there's a right or wrong way to run a startup, they are wrong.

I've seen startups in all kinds of verticals, from tiny tools making millions to huge tools with no revenue, B2C, B2B, and everything in between, technically challenging and easy. There's no one-size-fits-all formula.

3. Beware of specialized experts preaching their method.

When all you have is a hammer, everything looks like a nail. Every expert will sell their method, based on their reference experience and case studies. Not necessarily a bad motive in mind, it's just how they view the world. We tried cold outbound 3 times with different cold outbound experts and agencies, and it never worked. In the meantime, SEO was raking in all the revenue.

4. You can build a lifestyle business on almost any startup idea, even if bad.

It will be just radically harder and might feel like eating glass. The idea is a multiplier of your effort. You can build a business to a point where it generates enough money to support you, even when the multiplier is 0.

5. Getting people to pay for your idea does not always mean you have validated it

Be careful of selling $100 bills for $50. E.g., when you offer a lifetime deal or your personal time for services. Ideally, you want to get someone to pay you for a real problem. But finding real problems is tough (next point).

6. If you're targeting a saturated market, you need to look for implicit signals and incremental solutions, not "hair-on-fire" problems.

Everybody says fix the "hair-on-fire" problem, but that's hard to find if you are aiming at over-saturated spaces. People in them usually have too many solutions, paying for many and not even using some of them. That doesn't mean you can't identify angels to enter the market with incremental improvements. The success multiplier will be smaller, though.

7. Don't get sidetracked with all the marketing and sales opportunities.

If you are small, double down on the one channel that works for you. For us, that was organic traffic.

8. Consistency compounds, but slowly.

It took us 3+ years to reach meaningful traction, and we were making $2k MRR in the first 2 years. Unfortunately, there's no formula to know whether you are on the right track or running a zombie. Sunk cost vs. strategic persistence. You bet with your time.

9. SaaS multiples are often fantasy, especially for smaller businesses.

If you are below $1M ARR and/or have no aggressive growth potential, do not expect 7-12x multipliers.

10. Lifetime deal buyers aren't your real customers.

They can give you psychological validation, but they won't save your business. Make sure to segment your feature request and feedback between recurring customers and the rest. This applies to free users, too.

11. You only know if your founder is a good fit when your startup struggles.

First, it's the honeymoon phase, excited to start a new business. Then comes the though painful slug and extreme pressure to pivot. This is where most founders quit or move on to the next promising idea. Or stay and become a jointed powerhouse.

12. AppSumo can be a game-changer, but timing and market positioning matter.

Our $990k AppSumo launch worked because we had the perfect storm of conditions. There weren't any other good marketing automation tools in their marketplace at that time. We didn't create the demand. We just happened to be positioned when the market had a gap.

13. Frugality is a competitive advantage, not just survival.

We stayed profitable by being super frugal. This wasn't just about bootstrapping, it forced us to focus on what actually moved the needle.

14. Technical complexity doesn't guarantee success

Building more features, next feature fallacy, reaching feature parity with competitors. None of them is a guarantee for growth. That said, mature markets simply have higher tablestakes entry levels. That's why many micropreneurs focus on single-point solutions.

15. Founder-product fit is a must

Ask yourself – would I work on this for at least 5 years before starting it?

16. Hiring hesitation always costs more than waiting.

I learned to "only hire people when I feel 'hell yes' for them." The cost of a bad hire in a small team is big, it's better to stay understaffed than to bring on the wrong person.

17. You can actually close customers at conferences.

One of our first and biggest customers came from SaaStock. But you have to be strategic about talking with the right leads and arranging meetings before the conference.

I'm starting a new startup. If you want to follow my journey, check my blog.kalo.me where I share everything in public!

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Manu Goel
Wow! Real good read! What caught my attention most was ‘organic traffic’…what SEO strategies did you use and over what period of time did they show results?
Kalo Yankulov

@manu_goel2 Glad you like it!

SEO was tough even back in 2019-21. The strategy was:

  1. Start with founder-led content – e.g., personal experience and stories. Not connected to keywords per se. Goal was to bring initial traction and build a list

  2. Then, work on MOFU and BOFU pieces critical to the business. In our case these were words like "onboarding emails", "marketing automation for saas", etc.

  3. Once we had some traction and runway to invest in SEO, I built an engine with authors, proper wide-range keyword strategy and started targetting TOFU words, more pillars, long-tail keywords, etc.

    Frankly, I wouldn't do SEO like this today. I'd focus much more on founder-led content and unique perspectives and distribute across channels (Medium, Substack, other outlets, etc. ) vs. trying to keep the canonnical article on the native blog only. In other words, more mentions and omnichannel presence vs. trying to keep unique content on the blog.

    Hope that helps!

Manu Goel
@kaloyanyankulov you’ve got me thinking as really serious SEO wasn’t on my list
Kalo Yankulov

@manu_goel2 Organic is the sweetest channel of all, no doubt. Ongoing, scalable, cheap inflow of high-intent buyers :)

Thorin

This is a great list that highlights what works. But what mistakes did you make along the way?

Kalo Yankulov

@tmtabor We made a ton of mistakes, I'd need a book to write just a quarter of them :D

Thorin

@kaloyanyankulov lol. Fair.

Sanskar Yadav

This list hits the nail on the head, especially around grit being the ultimate differentiator. I believe there’s no shortcut to consistent content that builds trust and pulls in high-intent users. Curious about the mistakes you made too - those often hold the biggest lessons for all of us trying to build.

yagiz basaran

Man, real fire content 💥🔥. I'm kind of starting my journey and wonder -especially in B2C startups- how do you get users or lets say how did you convinced people that you need this app or website to make your life easy and fun!? Thanks in advance and congrats :)

Kalo Yankulov

@yagiz_basaran Solve a real problem they care about in a better or different way than competitors.

yagiz basaran

@kaloyanyankulov Thanks! Will research more about this.

Nika

How did you find the right co-founder? Or in other words: "make your relationship work even during though times"?

Kalo Yankulov

@busmark_w_nika That's a tough one for sure.

Here are some tips:

1. Work on a small project first and see if you gel.

  1. Clarify expectations before you begin work. There are great questionnaires on the topic. Fundamental things like what kind of company you want to build – big VC-funded behemoth or lifestyle, how many hours can you invest, do you have a runway, what do you like to do in the startup, why are you starting a startup, etc, etc. Here's one - https://proof-assets.s3.amazonaws.com/firstround/50%20Questions%20for%20Co-Founders.pdf

  2. Communication, communication, communication.

  3. Understand the attachment and work style of your co-founder — how they communicate, are they more open and closed, what movitates them, how they react to bad events. Most of the time your co-founder's negative behavior usually stems from their own stress, challenges, circumstances or insecurities – not from something you've done or said. The 2 most common styles are anxious and avoidant, with technical people often being the avoidant ones heads down coding/more introverted.

  4. Manage founder relationship debt. Address issues immediately, don't let them fester. Poor communication creates built-up resentment that becomes much harder to resolve over time. We made the mistake of avoiding difficult conversations by telling ourselves we were "too focused on the actual work," which ultimately led to bigger conflicts and nearly destroyed our partnership at one point. Share your emotions and feelings ASAP.

Highly recommend reading this article on co-founder relationship dept - https://scaleyourself.com/the-user-manual/relationship-debt-amp-the-level-3-conversation and this on attachment styles - https://scaleyourself.com/the-user-manual/know-your-attachment-style But also check the whole user manual, it's gold.

Kalo Yankulov

@busmark_w_nika I'm writing a long post/ebook on how we started, ran, and sold Encharge, and I'll share more on this there :) Make sure to follow me on blog.kalo.me to get notified when it's live.

Nika

@kaloyanyankulov Cool! You are also a Substack writer! :D

Kalo Yankulov

@busmark_w_nika I am :D

you're welcome

Andrei Tudor

That was a great read, thanks for sharing your learnings! As someone who's just joined the "startup founder club", I'm curious to hear what motivated you to keep pushing during the first 2 years, when, as you put it, "we were making $2k MRR". Did you have a feeling that it had to work? Did you have lots of signals to prove that time and continuous work are all you need?

Kalo Yankulov

@andreitudor14 Not at all. We just didn't have any other options :) Employment or giving up was not an option as trivial as it sounds.

Peilan Qin

Congrats on your journey! I love your point about persistence and the reality of lifetime deal buyers. What's your best advice for newcomers in saturated markets?

Kalo Yankulov

@peilan_qin Do not enter them :D The only way to beat Garry Kasparov is to not play chess against him. Choose a different game.

However, if you insist on competing in a tough market, ensure you have strong validation for a unique angle.

Peilan Qin

@kaloyanyankulov I get that! But what if I want to play chess? Any tips on finding that unique angle?🤣

Kalo Yankulov

@peilan_qin Same thing :) You have to select the battle; you can't beat them at their game. Segment and slice their audience until you are the best product for that small subset. Identify a problem that these people care about but your competitors don't or can't solve, and build that single feature that sets you apart.

For example, Attio managed to enter the CRM market by targeting modern, tech-savvy teams with a product-led motion who want to integrate their customer data into the CRM. They did it with a bloat-less, simple, and modern CRM. Something that no other CRM has been focused on before.

Another example is Savvycal — they didn't go head-to-head with Calendly and try to outcompete them on distribution and branding (impossible), they carved a space in the categry with a new more convenient "overlay your calendar" approach.

Peilan Qin

@kaloyanyankulov Thanks for sharing your thoughts! I totally agree that identifying a unique and competitive feature is key. The examples of Attio and Savvycal really hit home for me :D

Igor Lysenko

Thanks for sharing your thoughts on this. I don't think there's anything specific about the product; I mean, what should be done and what shouldn't be done. The word "flexibility" is the most relevant here.