accidentalciso

"Just start it and figure out the details later" is a little bit of an anti-pattern. Yes, it is generally better to do SOMETHING than to do nothing, as analysis paralysis is a very real problem, but business owners that completely wing it and don't plan for or manage risks that can be identified in advance are setting themselves up for failure.

I helped a friend get a consulting company off the ground a couple years ago. My official title was VP of Risk Management, and I was also responsible for service delivery (cybersecurity consulting). When he would talk about new ideas for the business, I would think through the logistics of what it would take to do it. He chastised me for being negative on more than one occasion, but I never once told him we couldn't do something or that it was a bad idea. I was always supportive and put in the effort to develop the ideas with him. He interpreted me doing my job and planning out what was going to be necessary to implement his ideas, manage risks, and make us successful as being negative.

I'm not suggesting that this is what is happening in your situation, but we, as entrepreneurs, often focus on what I call the "happy path" where things go as we expect them to. Rather than letting your wife's pragmatism bring you down, try to harness it as part of your idea evaluation and risk management process. Create a list of the risks or problems that she foresees and then think through the likelihood that the each event will happen and try to understand the potential impact to your business plan if it does happen. From there, come up with a mitigation plan for each risk in the list. The mitigation plans don't have to be huge, but putting them in writing will get you to think through them in a way that may help her feel more comfortable with the risks that you are taking. Remember, as your wife, those risks do affect her, too. Hopefully validating and addressing her concerns in a more "formal" way will make her feel better about things.

If you are considering starting a CPA firm, you might consider specializing in SOC2 audits. Cybersecurity is hot and will continue to be. SOC2 audits are becoming the standard (in the US at least) for companies to look to as a 3rd party attestation for Vendor Risk Management. You could definitely build out a CPA firm specializing in these audits to reach your financial goals.

$10-15k/mo. That’s at about 20 hours per week billable. I do cybersecurity consulting. I enjoy what I do. This next year I’m planning to adjust some contracts at renewal that should push my income higher. I’m also working on releasing a library of materials, some for free and some with a subscription to create some passive income as well. Also next year, I expect to have sub contractors helping with some of the service delivery to drive income higher without purely trading hours for dollars.

$10-15k/mo. That’s at about 20 hours per week billable. I do cybersecurity consulting. I enjoy what I do. This next year I’m planning to adjust some contracts at renewal that should push my income higher. I’m also working on releasing a library of materials, some for free and some with a subscription to create some passive income as well. Also next year, I expect to have sub contractors helping with some of the service delivery to drive income higher without purely trading hours for dollars.

There is a podcast called the side hustle show that you might like. I know they have done at least one episode on vending machine business. Look those up and also browse some of the other episodes and see if anything else looks interesting.

You are going to need to talk to a lawyer to help with your strategy. You might be able to get permission from the company to open source it, but don’t talk about it at all with your employer until you are working with a lawyer. They may have other suggestions as well based on what specifically your employment agreement says. Good luck!

By making your money work for you, instead of you working for your money.

What you are doing is referred to as Open Source Intelligence, or OSINT, in the cybersecurity field. It’s highly in demand and can pay very well. You absolutely can build a business around this skill.

This is creepy AF and is going to abused like crazy.

It sounds like it could be a fantastic customer for you if you can work with them to improve forecasting and establish mutually acceptable lead times. One question that comes to mind is do they actually need all of that inventory all at once, or could they take a portion of it immediately with weekly shipments thereafter until the rest is fulfilled? I don't think you're doomed, but you have some relationship building to do with this potential customer so that you can create a business arrangement that lets you ramp up and know that you'll continue to see a certain level of demand from them, especially if ramping up requires a significant investment in production capacity. Beware though, it is risky to have a single customer that brings enough business such that it gives them an unreasonable level of influence over your business. Not risky enough to not pursue the business, but something to think about and make sure is represented in your business risk management planning.

In high school, I could see a side hustle selling things like t-shirts, hoodies, and stickers being successful, as long as you can come up with cool designs. Those could be sold online easily, too. Selling candy might work (assuming the school allows it).

It’s all about your priorities and the decisions you make. You absolutely can be an entrepreneur and not be a greedy jerk. I’d argue that you will actually be more successful as an entrepreneur if you focus on relationships and building value rather than maximizing profits. It comes down to long term vs. short term vision.