Should I go all in or keep building on the side?

What I always recommend is: test the waters while still having the job. I wish my wife would have done it, but she didn't. You might have some contractual limitations there. It might make sense to read your employment contract.

What I would do is maybe put up a very simple home page. It's your first iteration that you're going to use to test the appetite.

Ideally, if you decide to go for this business, you want to be in a position where you can quit your old job and you already have new clients lined up. That's basically what I would do if I was in your shoes.

Slowly exiting your job as the startup picks up traction is my preferred way to start companies. The downside is that it takes a lot of time. If you're full time, maybe you could have done it in six months. Maybe on the side of a full time job, you did it in two years.

I started like that because I was a bit risk averse. When I quit my job and went full time, everything happened significantly faster.

When you're working on your startup in your personal time, it's really hard to feel momentum. Your personal time is by definition time that you need to unwind after work.

Every case has a lot to learn. You'll take those thinking models and apply them to startups. I learned so much more at my consulting firm than in school.

If you really absorb the experience and go all in, even for one or two years, then pivot to startup world, I think it'll be really good for you.

If you wanted to, you could scout for ideas on weekends. Start with who's actively seeking a solution. If you find that sweet spot, you can launch a prototype to test it. Once it clicks and people love it, you can decide, OK, maybe it's time to leave.

The concept of jobs is a little plastic. Now you have a job and a little contracting, then the job fires you and you do more contracting. Maintaining your own brand that can land you jobs or projects is very important. But you need an offer.

Also find something that gives you a reason to speak with people, so that you start creating a network. Back then, I doubly invested in resumes instead. It was a huge mistake.

At the same time, you can enter these conversations as the founder of something. That whole thing gets connected by one glue: you going out and speaking with people, the right people.

You should never start a company because you want to be rich or don't want to work for anybody else. On your own, with no company to give you a paycheck, an office and benefits, it's not easy.

The only reason you start a business is because you identified a problem for your target customers that continues to be frustrating, and you have a way of solving it that's unique, creative, different and better. If you think you have that today, I would absolutely not encourage you to leave your job. I'd tell you to put all your energy outside work into making your company a real thing.

If you're gonna get into panic mode while trying to build this out, I would urge you to pause and figure out how you're going to drive enough income to not have to worry about it. If you're in the lucky spot to not have to worry, congrats.

I've founded six companies. Every time, it either fails or is successful, or I move it to a side project and then I go get a job because that thing wasn't making money. I just go back and forth.

Six months from now you might need to take a job for stability and keep it as a side hustle. That's perfectly OK.

To a big extent, it's about what makes you happy. If working on your own thing makes you happy, you can take a discount.

But it depends on what the difference is. You have to think about how much of a discount in salary you're willing to take to work on your own thing.

Otherwise you can wake up in 15 years with a wife and two kids and zero savings. That happens because you were always doing your own thing and not taking the opportunities you had.

What's your criteria for saying this did not work out and you're going back to a job? Do you have a milestone, like six months in, that says it's working or that you need to reconsider? And do you trust yourself to stick to that and walk away?

If you quit, what's the downside risk for you? Can you be OK with that? Is there any excuse worth using not to do it? Doing it on weekends for a while is another option too.

You're not just spending all your savings on this. It's a gradual process. If you're already monitoring all this stuff, then it's a calculated risk.

The first company is going to fail miserably. There are no rules, it's just a heuristic. You can make it maybe with the second one, because your skill set increased.

Quite often I had conversations with people in their mid 30s who wanted to raise money so they could leave their jobs. They did something on the side, but something on the side is always limited because it's on the side.

I say, if I were to invest and pay you a salary, you don't have skin in the game, you just have a new job. Maybe you just need to collect savings and just take this risk.

I was completely depressed, so I needed somebody to give me directions, as an employee. In my case it worked, but I'm not in your shoes.

If you're not in that state of mind, "I'm a complete failure," maybe you don't need a job, but maybe you need a partnership.

Maybe you could go to some business and say: I noticed you have this pipeline, I can help you improve it. Just as a test, say: don't pay me, pay me after. Even if you don't make money, you can say you helped XYZ people improve by XYZ percent. That can be your social proof to position yourself further.