Let her go. Explain that you need to make cuts and that you can’t allow her to work for free. I’m pretty sure that would be a huge liability even if it was her idea. Give her a reference to whatever competitor you want to take down from the inside.

The business needs to be able to make change, especially if they accept only cash.

Outsourcing IT is one of the smartest things that a small business owner can do. I do cybersecurity consulting (vCISO) and specialize in small businesses (1-100 employees). It’s the right decision for almost every one of my clients. My larger clients will often have a dedicated IT manager that takes the lead but uses the IT MSP to get things done. It works very well and is so much less expensive than trying to do it all in-house. The one big thing I didn’t see in your list that I feel should be there at the $250/mo/seat cost is 24/7 Security Operations Center monitoring and response. Also, at that price, I would expect the laptop lease cost to be included as well managed backups for a full turnkey solution.

“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.

Unlimited PTO w/ 1-week mandatory PTO quarterly.

Grocery stipend, Costco Membership, Meal Plan Memberships (like Hello Fresh).

Door Dash subscription.

Cell phone stipend.

Streaming services subscriptions.

Mental health services and stipend for counseling/therapy.

Gym membership.

You didn’t mention tuition reimbursement, but that should be table stakes, too.

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.

Donate them to a local soup kitchen or something like that and take the tax write off.

$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.

This sounds like a scam. One of the primary things that scammers try to do is create presume through urgency so that their victims make bad decisions. Stay your course and let UPS do their investigation. That will be necessary for their shipping insurance to work.

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!

The family.

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

Interesting. I need to talk to my tax attorney about this. Would be a huge help for me this year.

Possibly PCI-DSS compliance for credit card processing. Possibly data privacy compliance depending on the state you operate in or that your customers are located in. Possibly sales tax reporting. Possibly insurance requirements for liability and workers compensation. Possibly 1099 forms for contractors and vendors. I’m sure there are more. Talk to your lawyer to make sure you understand the requirements for your specific situation.

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.

Lots of people talk about starting businesses. Few do, and even fewer succeed. I wouldn’t sweat it too much. At this point, you are already looking at retiring anyway, so if I were you, I’d just proceed with finding a buyer for the business and move on. If you do fire folks, you’ll probably need to do it quickly and ensure that their access to company systems is terminated immediately to prevent damage or data downloads. Letting folks go will put a lot of pressure on them to either organize very quickly to start the business or find new jobs. Most folks I know when presented with a sudden job loss will default to finding another W2 job. The group will end up scattered and more worried about themselves and maintaining their standard of living than taking the risk of starting a business.

I wouldn’t try to micromanage them, or you’ll be replacing and re-training a new person. If her numbers are good, that is what matters. If you replace her, would you expect their numbers to be better if hers are already similar to yours? I hate pushy sales, and I am less likely to buy from someone that pushes.

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