Ryan DeissCo-Founder & CEO, The Scalable Company

The Hardest Part of Entrepreneurship Nobody Warns You About #entrepreneurship

11 Jun 2026 · 1 min

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1:07

In this monologue, the speaker (Ryan Deiss) answers the question of what aspect of entrepreneurship catches founders off guard once they are actually running a company. While many focus on ideas, funding, growth, and freedom, the speaker highlights the "hypocrisy of leadership" as the toughest part: having to hold employees and managers to standards that the founder themselves feels they cannot yet meet. He describes the feeling of being out of depth, the internal conflict of demanding accountability while doubting his own competence, and the accompanying emotions of stress, loneliness, and decision fatigue. The speaker frames this discomfort as an inevitable part of growth, emphasizing that founders must stay in the trenches, continue building, and eventually grow into their roles despite the momentary pain of hypocrisy.

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Storfries asks, what's the hardest part of entrepreneurship no one warned you about? Everyone talks about ideas, funding, growth, and freedom, but once you're actually running the business, what part hit the hardest? Decision fatigue, cash flow, people, stress, loneliness, or something else? Curious what caught you off guard and what you do differently now. For me, it was the general hypocrisy of leadership, because when you are a leader, when you are running a company, what you have to do is you have to hold your people accountable. You have to hold them to a standard and you have to demand that your managers do the same thing when you yourself know that you are completely out of your depth. You know that you don't know what you're doing. You know that you're likely not meeting your own standards, and so you feel like this hypocrite, and I'll tell you, it's kind of 'cause you are, but that's what growth looks like because at the end of the day, this is your company. You don't get to fire you. You have to stay in the trenches. You have to stay in the gap building this thing, and yeah, you've gotta hold your people very often to, a standard that you yourself are not meeting, but that's what growth looks like and it sucks in the moment. Eventually, we do grow into our roles, but yeah, the hypocrisy of it all, that's the one that definitely caught me off guard.