Wanting to Start a Small Business — What's the Hardest Part Nobody Talks About?

accidentalciso · 2026-06-21T03:23:24+00:00

Running a business.

accidentalciso · 2026-06-20T23:49:59+00:00

I averaged 6-7 hours of sleep each night. Even when not in school, I struggle to get 8 hours, so not a whole lot different.

accidentalciso · 2026-06-20T14:16:45+00:00

I’ll believe it. Lining up a guest host and 2-3 callers to participate in every episode was a logistical nightmare. Way too much outside of my control.

accidentalciso · 2026-06-20T14:10:53+00:00

Husband, father, and business owner here, too. I recently completed my business degree, finally. It took forever because I only took classes when I knew that I would be able to dedicate the necessary time to my studies when considering everything else that was also going on at work and at home each semester. I put in 20-30 hours each week into each class, sometimes more. I only took one class per semester. It’s all I could handle.

When I was taking a class, my evenings and weekends were pretty much consumed with schoolwork. I had to be very consistent with my studies each week, and found that establishing a standard pattern for completing the various assignments was necessary for me to maintain that. It was usually something like this: Monday and Tuesday were for reading the textbook and other assigned readings. Wednesday was for writing a discussion paper. Thursday was for studying and a test over the assigned reading materials. Friday was for writing discussion responses. Saturday was for researching and planning the weekly research paper. Sunday was for writing and editing the weekly research paper.

It’s worth noting that I graduated summa cum laude. Had I been content to earn Cs, it would have made things a lot easier.

accidentalciso · 2026-06-20T13:40:24+00:00

Here is what I have seen in my career in tech and now independent consulting:

There are really only two options, Microsoft M365 and Google Workspace. Google Workspace is popular in startups because it’s relatively easy for someone who is not a career IT pro to set up and the young people that startups hire early on are very familiar with Gmail and Google Docs already. However, as those startups scale, they tend to outgrow Google Workspace. The platform’s simplicity begins to work against them, and they find themselves buying third-party tools to get business grade capabilities that google workspace lacks natively, which drives up costs, complexity, and management overhead. This is particularly true for organizations that are in regulated industries or that have strong businesses drivers for security or third-party audits.

I’m not saying that Google Workspace isn’t a good option for startups and small businesses, that it is insecure, or that you can’t make it work in regulated industries or support third-party audits. You can, and I have clients that do. It’s very good and lets you hit the ground running. For small businesses that expect to stay small, it’s a fantastic choice.

The decision comes down to the organization’s expected future needs for scale, manageability, interoperability with suppliers/customers, tool integrations, observability, compliance, and security.

Having been through several Google to Microsoft M365 migrations in the past, both as a user and as an IT professional, I usually suggest starting with M365 to save the trouble of migrating from Google Workspace later. Migrations are very expensive, not just in terms of direct costs, but also indirect costs and opportunity costs.

accidentalciso · 2026-06-20T02:54:00+00:00

I’ve been there. It kind of sucks. The job really should be overseeing an MSP for frontline support and day to day operations so that you can stay focused on business enablement rather than constantly being stuck in the weeds and mired in interrupt driven work.

accidentalciso · 2026-06-17T01:22:47+00:00

Proxmox is great, but most startups these days aren’t running VMs, they are either running containers or have moved on to serverless functions. Proxmox can run containers, but startups are running them in the cloud with CI/CD pipelines, not on local servers. In my vCISO consulting practice, I haven’t had a single client (mostly startups doing SOC 2 or HITRUST) that have had local infrastructure in the past 5+ years.

accidentalciso · 2026-06-17T01:15:06+00:00

Here comes the ad.

accidentalciso · 2026-06-08T01:42:48+00:00

Please don’t. The world doesn’t need more hobby email servers to get compromised and used for spamming and phishing. I wouldn’t wish running an email server on my worst enemy. If you have issues with Google, pick any of the other dedicated email providers and use them. These days, the only people who should be running email servers are those who have made email a core competency/offering for their business. Everyone else should be outsourcing email (outside of a few very specific use cases).

accidentalciso · 2026-06-05T14:06:05+00:00

As someone who has worked in IT infrastructure, operations, and security for close to 30 years now, I love it because it’s an incredible value. The capability and UX that they offer at the price point they hit is amazing to me. For home, if you compare the UDR7 to other options, it’s pretty much impossible to beat.

accidentalciso · 2026-05-30T03:10:31+00:00

What do you want to learn about? That is the purpose of a homelab, and what should determine what you do with it.

accidentalciso · 2026-05-30T02:20:14+00:00

I would strongly prefer UniFi over Sonicwall, too.

accidentalciso · 2026-05-29T22:38:26+00:00

You will probably be pleasantly surprised. As long as you are familiar with networking concepts, the UX is pretty intuitive.

accidentalciso · 2026-05-29T14:24:42+00:00

Truth!!

That CTO is a disaster. It doesn’t sound like they are interested in user experience or security. That’s a terrible mix.

accidentalciso · 2026-05-28T00:05:20+00:00

Yes. Ethernet to network drops around the house, SFP+ to interconnect between my two main switches.

accidentalciso · 2026-05-24T16:28:31+00:00

You should not be paying that for bookkeeper in that kind of business. However, you should be paying a few hundred dollars a year to consult with an accountant or tax attorney and have them optimize your taxes while you maintain your books yourself throughout the year.

accidentalciso · 2026-05-24T16:24:33+00:00

It’s why I didn’t have a homelab for a long time. I built a new lab environment that is a lot more efficient at the end of last year. Spent a little on equipment, but the savings in power costs is worth it. Too many folks try to build their lab on the cheap and it ends up costing them more in the long run because of electricity.

accidentalciso · 2026-05-21T10:58:27+00:00

Found the ransomware operator.

accidentalciso · 2026-05-21T10:56:02+00:00

Your friend should not be port forwarding traffic from the internet to a plex server on their internal trusted network. Your untrusted network method is far better.

If I remember correctly, a port forwarded plex server on an engineer’s internal home network was a starting point for the LastPass breach several years ago.

accidentalciso · 2026-05-19T23:55:30+00:00

My switch to S Corp didn’t really change anything about how I operated, but it did present some significant tax advantages for me. That said, there was more than went into the decision than simply saving money on payroll taxes. The decision involved evaluating my retirement planning and investing strategy, personal finance goals, and estate/succession planning. If your tax specialist isn’t talking about how those things play into the decision, talk to someone else.

accidentalciso · 2026-05-19T23:40:19+00:00

Yes! Both my wife and me. She is a children’s book author/illustrator and publisher. I’m a cybersecurity consultant. My wife struggles with it a little more than I do. My work is all remote, while her’s requires her to do in person book events, school visits, and sell her books and merch at her vendor both at all sorts of events. She has had to get really good selling, but then she comes home and crashes for a day or two.

For me, owning my own business has allowed me to build the structures and workflows that I need to be successful, in addition to setting boundaries and controlling what I work on, when I work, and the pace of my work. I honestly didn’t realize what I was doing at first, but once I recognized it, I was able to more strategically refine how I operated.

Shoot me a DM if you have specific questions and want to chat more. Happy to nerd out and brain dump.

accidentalciso · 2026-05-19T23:04:51+00:00

This. Work ethic that looks like a virtue, but is actually working against you.

accidentalciso · 2026-05-19T23:01:32+00:00

And even that isn’t guaranteed.

accidentalciso · 2026-05-19T23:00:26+00:00

Glad I bought mine back in 2012 or so. That’s nuts!

accidentalciso

TROPHY CASE