About 4 months ago, Chris and I launched MyVilla, a startup that aimed to make vacation home ownership easier and more affordable for a greater number of Americans. One of the requirements to grow and scale the company was that we could secure debt financing from banks or financial partners that would allow us to continue purchasing more homes and offer financing to our customers. For months, Chris and I have been dancing for dollars, trying to convince any bank or financial partner to provide us capital so that we could begin acquiring houses. Our financial modeling called for 10 houses this year which would require about $20,000,000. We had countless meetings with potential financial partners and they all started off the same way… The banks would basically say: “We love the idea and you have a great pitch and financial modeling. This is infinitely financeable because you are offering a personal guarantee and it’s secured by very valuable properties.” However, the excitement from these first meetings would soon fade. After weeks of providing extensive documentation, we'd either receive a flat "NO" or be ghosted. It was brutal. It left me with a mixture of emotions. From sadness, to anger, to self-doubt, and guilt. But what I just realized a few days ago was that I was experiencing something I hadn’t encountered in a while: Rejection. It stings. It’s tempting to blame external factors like the banking crisis, interest rates hitting the highest they have been in decades, and a potential implosion of the commercial office real estate market. But I’m the founder and CEO. It doesn’t matter what is going on with factors that are outside of my control. The responsibility lands squarely on my shoulders and I accept that responsibility. I’m constantly questioning myself with unanswerable questions: * Did I pitch it wrong? * Should I have pivoted and found a way to scale the company without banks? * Should I wait it out until the banking crisis hopefully resolves itself in a year? * Should I talk to a hundred more bankers? * Am I a quitter and giving up too soon? * Do all startups experience this many headwinds and I’m throwing in the towel too soon? Startup founders are told tons of conflicting advice. We are told: “never give up”. But we are also told, "fail fast”. We are given examples of Jeff Bezos persistence in pitching and hearing NO from 60 different investors before he finally heard a YES that allowed him to start Amazon. Then we are told of the famous pivot where a podcasting company Odeo pivoted and became Twitter. I’m never sure of which advice to follow. Should I keep going and throw good money after bad? Should I pivot or fail fast? I don’t know and I may never know. The future of MyVilla is uncertain but if it fails I will have lost a decent amount of my own money but what is much more troubling to me is that I will have lost one of my best friends some of his hard earned money. That makes me feel terrible. Of course, Chris has been a mensch about it and his wife Laura has been incredibly understanding. But the bitter feeling of losing a friends money is just awful. At first I thought my sadness was because of the failure of the business, but I quickly realized it was the uncomfortable feeling of knowing that I let down the people that believed in me. (Of course they would all say I didn’t let them down because they are amazing people. But the feeling is still there.) Yes, I know that failure is a risk in any new venture. My rational brain can tell myself that - “without risk, there is no reward”. I can reassure myself that this isn’t a failure - it’s just an investment and I gained a lot of knowledge from it. These things are all true. But this is the difference between reading business books and listening to podcasts about business versus actually starting a business. It’s one thing to read it and know it intellectually in your head. I