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I have been mostly unemployed since the dot com implosion of 2000–2001. I made a small packet of dot com cash that helped me in the early years. Not retirement

I have been mostly unemployed since the dot com implosion of 2000–2001. I made a small packet of dot com cash that helped me in the early years. Not retirement level money, but enough to supplement cash from infrequent consulting gigs. And enough with my spouse’s income to qualify to invest in startups either directly or via venture capital funds. I’ve applied to hundreds of companies across the industry since 2002. Multiple roles from low level programmers to mid–level managers and executives. I had been the CTO of a fairly large company in the 1990s. None of my experience mattered. There will be hiring managers from FAANG jumping in here saying “no, no, no, we absolutely look at your experience” and I’m here to tell you with one anecdotal data point that they don’t. So I’ve withdrawn entirely from the industry. Happy to sit back and watch companies repeatedly make the mistakes that I made and learned from in the 1990s. In turn I’ve been building and profiting from my own businesses over the past decade. Investors reject them as “lifestyle” businesses because they only earn a few million US$ in profits every year. But that’s plenty for myself. I have no investors to answer to, few employees to cater to, and it’s a lot easier than constantly trying to play catch up with whatever the rules are for either getting employed in tech (you’re not all FAANG companies, stop interviewing like you are) or invested in by venture capital (expecting every company to have unicorn returns is how you get Theranos and FTX). Between the businesses I own and the investments we’ve made we’ll do fine as we slide into our 50s and 60s. Build a small business. Get it going. Hire a kid to do some of the work. Grow some more. Hire another kid. Keep iterating until your “work” is checking in on people, then hire someone to replace you as the manager of the business and start another one. Constantly killing ourselves to hit the big payday in tech is like spending every last dime on lottery tickets in the hope that you’ll get that one big payday. It’s a lot healthier and saner to just spend the money on yourself or invest it in your own business. It’s probably not going to be a gajillion dollar payout, but it’s going to be more satisfying.

silisili 4y ago
Honestly, it sounds like you're living the dream. Any advice for starting a small business? I feel like my biggest hurdle is I just don't have any good ideas. Don't need millions in profit, heck even high 5 figures would tickle me pink.
- u2fsdgvkx19gb0i 4y ago
  If it’s just you, set up an LLC. If you have significant assets to protect, set up an S or C Corp. If you raise friends & family money get an attorney to draft the organizing agreement (LLC) or corporate documents. Highly suggest finding a good, local, business attorney to help at this stage and with any contracts. Learn the very basics of accounting for a small business. Pick a platform and make the effort to learn how to use it. I do my own bookkeeping but have an accountant who handles all of my personal and business tax filings. Put enough money into the business to get it going and handle the overhead (filings, mandatory taxes, regulatory fees, the lawyer, the accountant or bookkeeper, etc) for at least six months to a year. Make some effort to learn the rules, regulations, laws, both the spirit and intent, in your local jurisdiction. My personal experience has been occasional screwups (on my part) with filings that can be resolved with a mix of contrition and penalty fees as well as whatever is needed to cure the problem. With the exception of food handling, I’ve found most bureaucrats are just dealing with the same BS regulations we are, but from the enforcement end, and are just following the letter of the law (because it’s their jobs if they don’t). Don’t piss off the low level bureaucrats you’ll end up dealing with. If you want to effect change make political donations and find a politician to sponsor a law or regulatory change. As far as business ideas…I’ve built products after consulting gigs, inspired by problems I saw customers/clients encountering that were not the primary focus of my consulting work. I also go to the occasional local business networking events, not to prospect for clients but to talk to people and find out what sorts of problems they’re encountering. Look for patterns and commonalities and figure out if there’s something to build there, and will it be profitable? There’s thousands of businesses who are happy to pay hard cash if you solve their problems for them. The core of capitalism is providing an effective solution to someone’s problem that is priced to be cheaper than their solving it themselves. Don’t skip on support. If you can’t do it yourself hire someone at a low but decent wage to “answer the phone” (whatever that means today) and act as your Level 1 support. My rule is something I build has to break even fairly quickly. No hard and fast time limit, if something is gaining customers slowly and should hit break even in a year I’ll keep it going. Don’t use app store pricing. Figure out your fixed costs and charge some multiple. This is the inverse of the standard internet give it away for free and slap advertising on it. Online advertising simply doesn’t cover costs let alone provide profits at small scale. And I aim for small scale. 1000 customers paying $99/month to me with a decent profit margin is far better than 10,000 customers paying $9.99/month especially when you deduct the vig from Apple or Paypal or whoever you’re using for credit card processing. We’ve been conned into believing only giant huge problems are worth solving by the technology media and VC driven news cycles. There’s a lot of “small” problems that can be solved by relatively simple solutions (compared to FAANG level problems) but get ignored because they’ll “only” drive US$1MM-$10MM in revenue.

silisili 4y ago

Honestly, it sounds like you're living the dream. Any advice for starting a small business? I feel like my biggest hurdle is I just don't have any good ideas. Don't need millions in profit, heck even high 5 figures would tickle me pink.

u2fsdgvkx19gb0i 4y ago
If it’s just you, set up an LLC. If you have significant assets to protect, set up an S or C Corp. If you raise friends & family money get an attorney to draft the organizing agreement (LLC) or corporate documents. Highly suggest finding a good, local, business attorney to help at this stage and with any contracts. Learn the very basics of accounting for a small business. Pick a platform and make the effort to learn how to use it. I do my own bookkeeping but have an accountant who handles all of my personal and business tax filings. Put enough money into the business to get it going and handle the overhead (filings, mandatory taxes, regulatory fees, the lawyer, the accountant or bookkeeper, etc) for at least six months to a year. Make some effort to learn the rules, regulations, laws, both the spirit and intent, in your local jurisdiction. My personal experience has been occasional screwups (on my part) with filings that can be resolved with a mix of contrition and penalty fees as well as whatever is needed to cure the problem. With the exception of food handling, I’ve found most bureaucrats are just dealing with the same BS regulations we are, but from the enforcement end, and are just following the letter of the law (because it’s their jobs if they don’t). Don’t piss off the low level bureaucrats you’ll end up dealing with. If you want to effect change make political donations and find a politician to sponsor a law or regulatory change. As far as business ideas…I’ve built products after consulting gigs, inspired by problems I saw customers/clients encountering that were not the primary focus of my consulting work. I also go to the occasional local business networking events, not to prospect for clients but to talk to people and find out what sorts of problems they’re encountering. Look for patterns and commonalities and figure out if there’s something to build there, and will it be profitable? There’s thousands of businesses who are happy to pay hard cash if you solve their problems for them. The core of capitalism is providing an effective solution to someone’s problem that is priced to be cheaper than their solving it themselves. Don’t skip on support. If you can’t do it yourself hire someone at a low but decent wage to “answer the phone” (whatever that means today) and act as your Level 1 support. My rule is something I build has to break even fairly quickly. No hard and fast time limit, if something is gaining customers slowly and should hit break even in a year I’ll keep it going. Don’t use app store pricing. Figure out your fixed costs and charge some multiple. This is the inverse of the standard internet give it away for free and slap advertising on it. Online advertising simply doesn’t cover costs let alone provide profits at small scale. And I aim for small scale. 1000 customers paying $99/month to me with a decent profit margin is far better than 10,000 customers paying $9.99/month especially when you deduct the vig from Apple or Paypal or whoever you’re using for credit card processing. We’ve been conned into believing only giant huge problems are worth solving by the technology media and VC driven news cycles. There’s a lot of “small” problems that can be solved by relatively simple solutions (compared to FAANG level problems) but get ignored because they’ll “only” drive US$1MM-$10MM in revenue.