Ragnar Sass, angel investor and founder of Pipedrive, asks himself 24 questions before investing in a startup

Ragnar Sass, a founder of PipedriveLIFT99, and Salto, has published a list of 24 questions he always asks himself before deciding to invest in a startup or negotiate a partnership.

Ragnar Sass, image: LIFT99

“Two years ago, I published 16 questions, what I ask from myself before making an angel investment. In last 24 months, I have looked 4,000+ startups & made 20+ investments. Indeed – I have learned A LOT working with amazing founders, who have inspired me heavily to update my list,” he says.

Here is the full list of these questions:

  • Can I explain this business & why did I make the investment to my mom?
  • What positive impact will it have on the world & can it make the World a better place. Like IN REAL! Numbers, please.
  • Will they give back to the community & create a new environment for the future unicorn founders?
  • How useful & relevant is my personal experience & know-how for this startup?
  • Are they cool enough that I’d invite them to my own home for dinner?
  • Would I hire these folks to my own team?
  • Are they SO good I could imagine them as co-founders in my next startup?
  • Are they really self-confident & extremely positive?
  • Is any of the co-founders have what it takes to be the CEO of a 400+ person company?
  • Does a CEO LOVE to sell their product?
  • How proud & excited I would be as an investor (= team member ) of this startup?
  • Are they ready for BIG risks?
  • Why is the team so excited about the product?
  • Have they managed to turn me into its biggest fan?
  • How many folks in my network could be useful investors for this exact startup?
  • Can I make a list of at least three of my good friends whom I call so they should join the company ASAP?
  • What could I win & learn personally from this journey if the startup fails?
  • Can I imagine investing in the same founders if they start their next company?
  • Do they really care about company culture & PEOPLE?
  • Can they hire people who are much smarter & much much more experienced?
  • Can I explain to my wife why I have a call with a founder at 01.00 AM or during a romantic vacation?
  • Would I trust them asking advice about the next investment opportunity?
  • Will they survive a full pivot? Or the second one?
  • Would this founder survive a 100 km boat marathon with me as a co-pilot?

Who is Ragnar Sass

Ragnar Sass is an active angel investor, entrepreneur, and co-founder of the Estonian unicorn company Pipedrive, Salto Network, and Lift99.

According to the Salto website, Ragnar Sass invested in 20+ startups globally; helped numerous companies to grow their teams from 10 to 200+; co-founded Garage48 and mentored hundreds of startups across 80+ global hackathons. 

“All my passion & energy is help to build fast-growing startups. Starting from values, hiring best talent & grown them with rocket speed.”