4 Ventures and 30 Lessons: Unlocking Startup Secrets

From the weirdest places I’ve pitched in, all the way to understanding harsh truths: Startup revelations without sugarcoating

“Let’s talk”, replied the investor who just received my fresh pitch deck for feedback purposes.

“So it’s true what they say: ‘ask for advice and receive money’!” I got excited for a mili-second.

Then I read the rest of the email.

“There are way too many comments to share over an email. Are you available for a call later this week?...”

I’ll cut to the chase: not only did I never raise money for this particular startup, but I actually never built it.

After starting a consultancy and founding a global services company, I thought I was ready to dive into the startup ocean. I had a potentially good idea, in a field that was my domain expertise, at the perfect timing (shortly after COVID, when markets were rising without signs of stopping). 

Yet I lacked many other essential ingredients, which in hindsight - if I were the investor - I would never put my money on those stakes. 

Who knew that an interesting idea and some enthusiastic potential buyers were simply not enough to build a startup? 

Well, apparently everyone with real startup experience knew. 

Since then, I’ve built a startup that generated revenue before the MVP was complete; and currently building another one with a much more ambitious product and tech moat, already backed by VCs (Eloo is enterprise software for building smarter products faster, by translating requirements into engineering specs).

I decided to write the guide I wish I had back then. I’m here to share the lessons learned through sweat and tears (thankfully no blood). 

Hopefully, for the visionaries amongst us, it will help to stay grounded while turning those dreams into reality.

1. Start with the problem, not with the solution in mind. It’s really tempting to fall in love with a technology or an idea for a product. But in reality - those almost never correspond with the real problem that needs solving. Explore problems, then craft solutions.
2. Your solution shouldn’t come up in the first validation call. Asking users if they’d use XYZ will probably yield a reply along the lines of, “Sounds interesting… I’d probably use it!”. Translation: “I’m being polite, now please let me go back to do my work”. Don’t talk about your solution as the starting point. Go back to number one on this list and ask about problems or a specific problem. Revert to the sketching board, make sure you’re meeting the need, and only then show them your solution. 
3. Ask how they're solving the problem today. Inquire about their current tools, processes, and habits. You might find out that they do have a problem, but they have zero interest in a digital solution to solve it, and they do just fine without it. Or, you might find out WHY no one has attempted to solve this before. That shouldn’t stop you from trying to solve it, but you’ll learn a lot about the direction of a potential solution.
4. Assemble the best team ever. Don’t compromise on people. Your idea will change; Your market will change; You’ll pivot; You’ll adjust. But your team is your anchor. Invest in the best core team you can gather.
5. Start building 'quick and dirty'. Don’t wait for a fully polished product. Don’t start with deep, well-structured tech before putting something quick in front of your users’ eyes, to make sure it resonates with them. It’s cheaper and faster to build with a simple no-code tool and create most of the work manually behind the scenes, in order to understand what users really want and need.
6. If they aren’t putting the money where their mouth is - the problem isn’t painful enough. That’s self-explanatory. 
7. Talk about your idea. I know, I know. You’re afraid of competition. Don’t be. If your idea isn’t differentiated enough and anyone can copy it once they hear about it - think again if it’s worth building. Talking about your idea - not necessarily publicly but with the right people - goes a long way in opening doors, creating investment opportunities, pulling in potential users, discovering more competition, receiving valuable feedback, and whatnot. 
8. Open your mind about who the competition is. Netflix competes with sleeping hours and social time. Automated billing competes with human bookkeepers. Don’t look just for other tech solutions; think broadly about who or what you’re replacing for your users, and who you should keep in the back of your mind as a potential future competitor.
9. Differentiation isn’t about having a better feature. One of Wayz's founders once told me a story: “Every month, we heard about a developer who has built a parking space tracking system. Then one day we finally had the time to prioritize this feature; the competition vanished overnight”. Lesson of the story? If you’re building your entire startup as something that could have been a feature of an existing product, you’re risking your company’s existence. 
10. A waitlist is not a commitment. Everyone can get enthusiastic about a new product. Putting a name on a waitlist - while being a good signal - is not a commitment. You want to look for some skin in the game, either via time or money they invest in using your product.
11. List the hard questions investors will ask you - and pose them to yourself. The purpose is not to please investors; the purpose is to build a highly successful and sustainable company. If you can’t honestly ask yourself the harsh questions, the harsh reality will bite you.  
12. Think hard about whether you’d invest the money if you were in the investors’ shoes …If not, don’t ask for money yet. Go and fix what’s broken, bridge the gap, fill in the holes - you get the idea. 
13. De-risk yourself constantly. Feel safe and sound with your startup? You need to start worrying. Never let smugness creep up on you, keep spotting potential risks and plan how to mitigate them.
14. Sketch the flow until it’s flawless. When you can imagine your solution - that’s good. When you can write it down, draw it up, and sketch it in depth - that’s much better.
15. Add up the real numbers, not the optimistic ones. Better safe than sorry; you really don’t want to find yourself running out of cash simply because you didn’t budget employer costs, insurance, IT equipment, and all those bits and bytes that we love ignoring in the hope they disappear.
16. Budget your runway obsessively. You should be able to tell it out of your sleep.
17. Don’t look for users; look for crazy-in-love early champions. Those champions are not only your golden path the Product-Market-Fit - they’re your best marketing channel, and the proof that you’re building a loveable product that people can’t ignore. 
18. Look for talent in unexpected places. Nothing wrong with recruiting from FAANG companies, but let’s be realistic: very few of them will leave those golden cages to come to work with you on your startup. Look for excellent talent in unexpected places; Look for the pirates, the innovators, the crazy ones with the spark in their eyes. It takes one to know one.  
19. Don’t fall into a victim mentality. No one owes you anything. If you can’t get the funding - not all investors are idiots. If you can’t get the customer - the users aren’t stupid who “don’t know what’s good for them”. Try to figure it out rather than falling into self-pity or rightfulness.  
20. Let the team take ownership from day one. You own the company? Good for you. Now how do you make your team feel like this baby is theirs as well?
21. Time-frame your project planning aggressively. 'I need another week. Just one more month to get the funding. With a quarter more, the product will be much better'. Suddenly, before realizing that, you ate through your savings and three other startups just launched a similar product. Move fast and use zero excuses.  
22. Great products lose to great spreadability; plan your GTM from day one. Even if you have the best tech in the world that could actually save the world - no one will benefit from it if no one knows about it. No, they won’t come if you only build it. You need to spread the word about it - and think about this obstacle from the moment the idea is born.
23. Design lean, plan for scale. A famous quote reads: 'what won’t be simple, simply won’t be'. This is how you want to start - simple and lean. But if you neglect thinking about scalability for this moment when things start to go well - oh well, that’s a startup-wrecker. 
24. No one will solve your problems; it’s up to you to figure it out. Truth bomb: You’re the one who’s in charge now. It’s not the investor, advisor, or customer’s job to guide your way (they can help for sure. But that’s different) 
25. Warm intros go a long way; start now. Still reading this? OK, finish this long list and go, already, to make some new valuable connections before you actually need them.
26. Don’t underestimate good storytelling, or rehearsing your pitch. No one cares about your great idea until you make them care. Data is not enough; two founders can present the exact same startup and receive different responses. Craft the most compelling story, practice on a few truth-tellers you trust, and rehearse, rehearse, rehearse. 
27. You’re pitching everywhere. Literally. I’ve pitched my startups on a plane, a restaurant (eating by myself and happened to meet someone relevant), a picnic by the river (that’s how I landed on IBM as my first customer), a kids’ playground, coffee shop, hotel lobby, on the street when busses roar by… the list goes on and on. Be ready to pitch everywhere, to everyone, at different lengths and styles.
28. Your co-founders are your everything. Make it work Invest in those relationships like it’s your marriage. Not kidding here.
29. Dream big. Now dream bigger. Know that moment when you feel your idea is too lofty, and you start doubting who are you to execute it, and there must be someone better out there… Stop. Seriously. Dream bigger. You meant to do it.
30. The first step is always the hardest to take …But once you’ve taken it, it’s a little easier to take the next one. And the next one. Before you know it, you’re more of a doer than a talker. 

I hope this piece will get you (at least) 1% closer to your startup & entrepreneurial goals. Happy building.