3 ms·

Hey Patrick, I have one for ya. What are the biggest mistakes you've seen early, seemingly unimpressive founders (and teams) make during a pitch or through runn

Hey Patrick, I have one for ya. What are the biggest mistakes you've seen early, seemingly unimpressive founders (and teams) make during a pitch or through running their company that turned you off - only to discover later that they were able to build impressive businesses? Conversely, what signals do you think you've perhaps over indexed on (positively) in the past that have potentially been "yellow" flags in a founding team you've invested in (or recommended) and led to a failure to thrive? Are there things new startup founders can learn from either scenario?

patio11 9y ago
Startups have a really long lifecycle associated with them. I have answers to the question with respect to startups I was not professionally engaged with. I don't have many data points regarding ones which I was, because the jury won't be in for a few years on the numeric supermajority of them. My set of data points where I have reasonable confidence in terminal outcome is very small relative to e.g. a professional investor who was active over the same length of time I've been on HN. This is not a new insight, but the thing pg says about successful startups often looking like a toy appears to me to be true. One benefit of having a searchable archive of my written thoughts going back 10+ years is that I can see what I thought of e.g. Facebook or Airbnb back in the day. In both cases, I thought they were unlikely to find a business model. I was very clearly wrong about that. I am, accordingly, very careful around the fact pattern "it's clearly something people love but is there really a business there?" Within my specific interest in B2B SaaS companies, a thing I have historically overindexed on is amazing product teams without demonstrated success in sales in the appropriate model (low-touch, high-touch, etc). I have sometimes been wrong about "Ahh, clearly they will figure out enterprise sales; how hard can it be if they can clearly ship a good product?" It is, in fact, possible to be a great product owner and not successfully build a sales organization strong enough to take a company to the sort of trajectory successful funded startups want to walk down.
- MediumD 9y ago
  What would you recommend for someone who is starting a B2B SaaS business with a lot of product experience, but virtually no enterprise sales experience. Obviously, hiring someone with enterprise sales experience/connections is our main priority, but how would one go about learning? There aren't really bootcamps & online resources for learning sales.
  - corobo 9y ago
    Forgive me for diving in here but I happened to read this article from patio11 just yesterday and think it might help https://training.kalzumeus.com/newsletters/archive/enterprise_sales https://training.kalzumeus.com/newsletters/archive/enterpris...

patio11 9y ago

Startups have a really long lifecycle associated with them. I have answers to the question with respect to startups I was not professionally engaged with. I don't have many data points regarding ones which I was, because the jury won't be in for a few years on the numeric supermajority of them. My set of data points where I have reasonable confidence in terminal outcome is very small relative to e.g. a professional investor who was active over the same length of time I've been on HN. This is not a new insight, but the thing pg says about successful startups often looking like a toy appears to me to be true. One benefit of having a searchable archive of my written thoughts going back 10+ years is that I can see what I thought of e.g. Facebook or Airbnb back in the day. In both cases, I thought they were unlikely to find a business model. I was very clearly wrong about that. I am, accordingly, very careful around the fact pattern "it's clearly something people love but is there really a business there?" Within my specific interest in B2B SaaS companies, a thing I have historically overindexed on is amazing product teams without demonstrated success in sales in the appropriate model (low-touch, high-touch, etc). I have sometimes been wrong about "Ahh, clearly they will figure out enterprise sales; how hard can it be if they can clearly ship a good product?" It is, in fact, possible to be a great product owner and not successfully build a sales organization strong enough to take a company to the sort of trajectory successful funded startups want to walk down.

MediumD 9y ago
What would you recommend for someone who is starting a B2B SaaS business with a lot of product experience, but virtually no enterprise sales experience. Obviously, hiring someone with enterprise sales experience/connections is our main priority, but how would one go about learning? There aren't really bootcamps & online resources for learning sales.
- corobo 9y ago
  Forgive me for diving in here but I happened to read this article from patio11 just yesterday and think it might help https://training.kalzumeus.com/newsletters/archive/enterprise_sales https://training.kalzumeus.com/newsletters/archive/enterpris...