SaaS, Tech and Business

10 expensive lessons from the startup world

In my experience as an investor, entrepreneur and startup advisor I have learned a number of lessons. They are fully aligned with the advice you get from startup and VC gurus, but at least for me, it takes a bit of pain in my wallet and my pride for the lessons to really sink in. I hope I can make it slightly cheaper and less painful for others, or even to prevent them from making at least one or two mistakes.

expensive

Startups are a wonderfully invigorating experience. I have been a full-time operator in two, have advised extensively five, have invested in over 10, and have seen countless examples. I find startups incredibly inspiring as a professional experience and startup people a lot of fun and learning to be around. You get to do almost everything in each function, you are creating something from scratch so you can move fast, without bureaucracy. You are inventing so you need to creatively design an experience for a customer. It is really a great package that is a lot of fun.

At the same time startups usually imply a significant short-term opportunity cost as most of the equivalent compensation is equity. And they can be very stressful, there is never enough time to do everything, and you experience a very quick succession of highs and lows. With the highs being very high, but the lows being really low.

In the last years, I have read a lot of stuff about startups. When I did my first one in the internet boom there was almost nothing, not even the term or the glamour. Now, you have great textbooks on how to do things and what pitfalls to avoid. Still, making a startup work is really difficult as a lot of moving parts have to fit and work out.

I have distilled the top 10 mistakes I have made myself or seen made. Nothing new but even if it helps just one person avoid a mistake well worth the time writing. They are mostly relevant to B2B tech plays, especially SaaS, which is what I am familiar with, but they probably translate to other domains too.

  1. Tech is king. A tech startup has tech in the name for a reason. It depends heavily on digital technology and as such tech talent is the key competitive advantage it has. Forget about the glitzy business plan, the domain expert, and the ex-consultant. Tech founders and tech talent are priority number one. Tech talent will determine your speed to iterate and your value for a potential exit. Tech giants like Facebook mainly buy and look for engineers, the rest is overhead.
  2. Pain-killer. Of course, many startups with outstanding tech founders fail. For the most part, this is because they build things no one wants or just “vitamins” that will make life better but are not absolutely necessary. Startups need to offer pain-killers for a big bleeding wound that someone has. Alternatively, they need to pander to one of the seven deadly sins as Linked In founder has famously said. If people don’t scream for your product you probably are onto a “nice-to-have”. That is going to take too long to sell to survive, even with people telling you that they should be using it.
  3. CEO Sales leadership. The CEO is, among many other things, the salesperson-in-chief and evangelist of the company. A CEO that doesn’t go out to sell will have trouble finding traction. This is especially difficult for technical founders that sometimes are not used to sell and communicate. Of course, selling only means in-person selling for some products, but the CEO will always need to be close to the customers to listen to what they really need. A CEO that isn’t always selling their product (in their own unique way) is a big red flag.
  4. Customer personas and budget. This is very much B2B, you need to know whom you are selling to and the budget line item you want to be part of. It might take time to discover, but it is inescapable. Only people with budgets buy products, and people have job titles and worries that come with them. Even if you are selling to a small business owner that determines budget autonomously you will have to fit in some of her mental categories.
  5. Long-term commitment and passion. The stories you hear about startups in newspapers are about quick fame and riches. The stories you hear from entrepreneurs are about 7 to 10 years of hard work and overcoming disappointment. Your only chance to slog through those hard years with a steadily increasing opportunity cost is if you are really passionate about your goal. So take this as an at minimum 5-year (realistically 7+) decision and make sure you are so passionate about the topic that you will be happy even saying “at least we tried” at the end.
  6. Founder alignment and culture creation. Being co-founders is like a marriage, but seeing each other all the time and having grown-up kids that you have to motivate to work for much less than they could be making someplace else. You need to be totally aligned from the start and keep that alignment over time. Don’t paper over disagreements rather tackle them head on, get your prenuptial agreement (aka shareholders agreement), and make sure you agree on which culture you want to build.
  7. Anti-goldilocks talent. Talent in startups is tough. You have infinite work so you would want the best talent, however, you always have insufficient money so you always want the cheapest talent. As the CEO of Blackline said in the last SaaStr you have to choose two of cheap, talented and not crazy, and you can’t afford anything but cheap and talented. The consistent advice I have heard is to go towards three extreme profiles: (1) a few absolute stars that have done it before, as they will drive incredible impact and leverage on others even if they are expensive, (2) many cheap, enthusiastic and hopefully talented very young talent that hasn’t much experience but wants to learn, and (3) talented people who are quirky enough that they find it difficult to work in large corporations. Avoid someone that is reasonably cheap, talented and sane, you want to go to the extremes, goldilocks talent is better for corporates.
  8. Funding. You need money for everything. Even if the amount is much less than ten years ago you won’t able to build the product, sell to customers or deliver them the promise without money. If you are short on money you will spend all your time worrying about it and solving the problems it causes. Of course, funding doesn’t mean VC funding. You can have customers fund your startup and bootstrap it successfully even if it takes a bit longer. Just avoid being unrealistic about being able to do stuff without money, or hoping that a round of funding will materialize from thin air. Money is your gas and you will get nowhere with your tank empty.
  9. Data and analytics. Product, Technology and Sales have been the traditional pillars of startup success. Now Data is claiming its place in the table. Analytics will allow you to create much better product much faster and to sell a lot more much more profitably. Who is your analytics founder? You need one, so get it from the start.
  10. Family sport. On a more personal level, you can’t get into this alone. Your family and your friends have to be your support group. You won’t be able to talk or think about anything else, you will work 24×7 (even if you can do it from home), you will only be making money at the end of the rainbow, you will have at least a couple of horrible downs per month, odds are against you. Have you told your loved ones what they are getting into? Have they bought the ticket? You’ll need your loved ones to get you through the bad times and support you in your probable failure so make sure they have your back.

This doesn’t intend to discourage anyone. The list of obstacles is long, but the fun and professional and personal growth for trying is amazing, even if you don’t get the pot of gold. Just be aware of what it requires to have a chance and what sacrifices you will have to make. Newspapers, LinkedIn, Twitter and business books only talk about the exceptionally good cases because that is what people like to see. You will experience the full distribution of potential outcomes and need to be ok with them, even if the end you manage to get to the pot of gold through hard work, talent and luck.

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