@andyellwood that's such a great question. Andy, I bet you feel the same, if you'd watched a few CEOs do things before you got a chance to do something... how would you treat it differently? I think my answer is a few things: 1. I would treat it as a marathon instead of a sprint - I had so much fear at my first company that we would die in the early days and nobody would fund us. I suppose that was a reasonable fear, because we did need to raise more capital, but despite that, I wish I had treated it with more of a measured METHOD. It would have prevented anxiety later on. The right way to treat a startup is almost like a march - just take a certain # of steps per day, enough to make it tough, but not enough that you aren't able to continue. 2. I wish I had surrounded myself with people that were going through the same thing much earlier than I did. A few years ago Michael Karn (who I think you know, Andy) started a CEO group; this plus CEO coaching gets you so much farther than you would be otherwise. It's super isolating to have a startup even if it's successful, so you need to have rituals that will keep your peers in your life where you can kind of blow off steam. I wish I had done that earlier.

@julien Love both those answers. Especially the idea of surrounding yourself with others that are in it - or have been. It is lonely for the founder and CEO most of the time, they will always care more than everyone else and all they want is someone to be able to see them in their full out and say, "keep going." I would add that while we can all convince ourselves that there is an opportunity and that someone should chase it down, that doesn't have to be you. There will be a ton of opportunities to chase down in your life if you continue to pursue innovation and solving pain points in your life. But wait for YOUR opportunity and YOUR all-in moment. You are going to be talking about this idea, industry, and solution for a long time once you dive in, make sure it is something that you care enough about that you are gonna love talking about it a decade from now. Your decade long passion will attract others that want to solve that problem and not just for the short term.

@andyellwood it's true, one of the nice things about tech is that you're constantly in front of new opportunities if you're smart and hard working. more are always coming.

@mark_yeramian you have an ability to build something totally on your own and see how it goes - if you are able to, to a degree make, design, and market yourself - this is more people than you think. another reason is that you utterly need to be your own boss. if you take on venture, you are building WITH others by definition, and that probably includes a board that you're going to have to build consensus with. a third reason is just the pressure of the timeframe. if you can make something happen on your own and want to build for youself, but you don't think you'll be able to build to the NEXT level of scale in the timeframe needed, then don't do it, because you're setting yourself up for future failure. honestly there are lots of reasons why NOT. another would be that you don't want to spend 10 years of your life doing a single thing - if you're not super oriented towards that mission, you're going to have trouble getting motivated about it. the main reason to take venture is that you have an idea that has SCALE - high TAM - and that you are going to need capital in order to scale it, or perhaps, even build it, and you don't have that.

@ericskiff it depends on how fundable they are. in the people that i am coaching i see founders with businesses doubling quarter over quarter with their investors being very confident about raising a financing. they have 12 months runway. but most people are not in this situation, nor are they failing - they are in between. those people that are in between need to develop certainty about something - either their burn rate, by increasing revenue or cutting burn quickly. those who have never done this don't understand how time works against them the longer they wait - while cutting $50k in burn per month gives them an add'l 600k, with 6 mo of burn that same cut delivers only 300k, which is not nearly so useful. often what founders need in this situation is just more certainty with their decision making. and in many cases they can find ways to cut costs and still keep their business going mostly intact.

@george_stamatis assuming the next round is coming automatically can be a giant mistake. typically it'll be harder than the last one unless your company is really taking off. regarding the biggest challenges i've faced, i think definitely watching my last company struggle and ultimately come down during / because of the pandemic was one of them. another i could talk about a number of different ways, but the main thing i didn't spend enough time on at my last business was hiring. my focus on finding good teammates now is much stronger than it was, so it turned out to be one of the most serious challenges i faced, even though i didn't know it at the time.

@jeremyr96 intensity and commitment are two of the top things to look for in people, which is especially important while working remotely. if you have these, it builds a mutual respect among people that is very valuable and that helps energize the team. we're all learning a bit as we go in the remote world, but that is what i think of as being important these days, in addition to to everyone caring about the customer and mission.