The hardest things about helping founders as an investor:
– Making the founder feel they’re not alone. It’s “against the odds” difficult to make a startup successful
– To not work from the position where the founder feels they need to interact like a subordinate
– Finding the balance between being supportive while maintaining necessary objectivity
– Knowing when to be hands-on vs when to step back and let founders find their own path
– Building genuine trust that enables founders to share real problems, what keeps them up at night
– Accepting that sometimes the best help is simply listening, not trying to solve everything
– Resisting the urge to pattern match too quickly based on past experiences
– Understanding that each founder’s journey is unique, even if challenges seem familiar