Having done this at various scales I can attest to the truth in this article. Fundraising is never fun, doesn't matter if it's $100k or 100MM. Fundraising is exhausting, it creates the deepest amount of imposter syndrome that builds with every meeting. The need to stay focus on what you're doing, how you got to where you are, and why you're doing it becomes a primary concern, having people around you who believe in you is key during this period, but even that often only treats the symptoms. This was an email I got from a VC a couple years back: http://john.je/tA3S - that wasn't a fun day. I think there is a lot of romance is building a scaled startup, but a lot of folks I know, even those who have had large exits say they'd preferred to have built a much smaller lifestyle business in a more organic manner. The real fact is, building and maintaining any business from zero is really difficult. Even though it can be incredibly rewarding, it's certainly very rarely much fun.