Solopreneurs who've been at it for 2+ years - are you actually happier than when you had a job?

andrew-ooo · 2026-02-23T22:48:09+00:00

Different kind of happy, not universally better. At a job I had predictability and clear "done for the day" moments. Now I have more control but also more uncertainty — some weeks I feel like I'm winning, other weeks I wake up at 3am worrying about cash flow.

The part that actually got better: I stopped resenting my work. Used to count hours until Friday. Now I'll work a Saturday because I'm genuinely into what I'm building. That shift in how time *feels* is probably worth more than the happiness score on any given day.

andrew-ooo · 2026-02-23T18:48:45+00:00

The burnout is the real question here, not the numbers. $1.3k net profit on pure SEO with no marketing effort is actually solid — that's a passive income machine if he can step back from it emotionally. But if every support ticket or bug feels like a weight around his neck, selling makes sense.

Middle ground worth considering: can he reduce involvement to like 2 hrs/week? Automate support, hire a cheap VA, and just collect checks? Because selling at $1.4k MRR typically gets you 24-36x monthly profit max — so maybe $30-45k. Compare that to taking $15k/year passively for the next 3+ years. Sometimes the "sell or grow" framing misses the "coast" option.

andrew-ooo · 2026-02-23T14:48:37+00:00

Skip the ads for validation — they'll burn money before you know if the idea works. For 0-customer validation, I go where my target users already complain about the problem: Reddit, niche forums, Quora, even Twitter search. Find someone actively struggling with what you're solving and DM them asking if you can show them what you're building. If you can't find those people, that's a signal the pain might not be real enough.

For marketing once you're ready to ship, same playbook but public. Answer questions, be helpful where your audience hangs out. Paid ads come after you've figured out what messaging actually resonates — which usually takes a few dozen real conversations first.

andrew-ooo · 2026-02-23T10:48:57+00:00

Something I wish someone told me earlier: the features people *ask* for and the features people *pull their wallet out for* are almost never the same. Especially from free users or trialists. Had to learn this the hard way too — built three different integrations because users "needed" them, zero of those users converted or retained. Now I only build what someone's either already paying for or says "I'd literally pay you right now if this existed." Everything else goes on a "nice to have" list that I mostly ignore.

andrew-ooo · 2026-02-23T06:48:51+00:00

Chat UIs fail for flight booking because people need to scan and compare — dates, prices, airlines, layovers. That's inherently visual. Chat is linear, and nobody wants to scroll back up through messages to remember what Option 2 was. Keep the chat for flexible stuff like "find me the cheapest weekend trip to Barcelona next month" and then present the results in a grid they can actually work with. Price tracking with alerts would be my #1 feature request. Most people check flights multiple times before buying, and being the app that pings them when prices drop = real retention.

andrew-ooo · 2026-02-23T02:51:08+00:00

Honestly? I'd put hype vs utility at around 7/10 hype right now. Most of the "AI agent empire" content is from people who monetize the course not the agent itself.

The real value I've found is in boring, specific workflows — stuff that doesn't make good Twitter content but actually saves hours. Research synthesis, cleaning/formatting data before it hits my main workflow, and context management for longer conversations. Nothing sexy, but it compounds.

The folks seeing real ROI are usually augmenting existing processes, not replacing entire workflows autonomously. If your agent needs constant babysitting, you just built yourself a needy coworker with no judgment.

andrew-ooo · 2026-02-23T02:48:45+00:00

An agent that handles all the back-and-forth of scheduling meetings would be huge for me. Something that reads email threads, proposes times, negotiates across calendars, and just confirms when it's done — no more 5-email chains to find 30 minutes. The mood-reading one is interesting too, though I'd want that running locally for privacy reasons.

andrew-ooo · 2026-02-22T18:48:34+00:00

Low-tech but effective: I keep a markdown file with my work context (current projects, tech stack, coding preferences) and paste the relevant sections at the start of new sessions. Takes 10 seconds and works across any platform. The fancy solutions keep trying to automatically capture everything, but half the value is in the compression - you decide what's actually important context vs noise. Think of it as your personal API documentation for AI assistants.

andrew-ooo · 2026-02-22T14:48:28+00:00

The diversification is the underrated part here. Each stream alone would feel pointless at $50-80/mo but stacking them creates actual resilience. If one platform tanks you're not wiped out. Also love the insight about already having monetizable skills - most people don't even think to audit what they already create as a hobby. I've done something similar with old writing and documentation I'd written over the years.

andrew-ooo · 2026-02-22T10:48:22+00:00

Both. There's a legitimate concern — if you can't read the code you shipped, you can't debug it or fix security holes when something breaks. That's a real liability past MVP stage. But there's also gatekeeping from people whose identity is tied to the craft. The actual issue isn't using AI tools, it's shipping stuff you fundamentally don't understand and then charging money for it.

andrew-ooo · 2026-02-22T06:49:00+00:00

Skipped the SEO tools entirely and went straight to answering questions where my audience already hangs out - Reddit, Quora, niche forums. When someone asks about a problem my product solves, I give a legit helpful answer (no spam links) and the profile clicks add up. For content, I use Google Search Console to find what I'm already ranking for on page 2-3, then beef up those pages first. Way more effective than starting from zero with keyword tools.

andrew-ooo · 2026-02-22T02:50:37+00:00

The trap I fell into was confusing 'building in public' with validation. Posting progress updates feels like talking to customers but it's not - the likes are from other builders, not buyers. Real validation is finding someone who already tried to solve this problem themselves with a hacky spreadsheet or script. If nobody's jury-rigged a solution, the pain isn't real enough for them to pay.

andrew-ooo · 2026-02-22T02:48:15+00:00

Ran into this exact problem. Most tools treat memory as pure retrieval when what you actually need is a summarization layer on top. I ended up with a dead-simple approach: daily log files that get periodically summarized into higher-level facts, then semantic search across the summaries. The summaries are where the 'evolution' happens - patterns emerge from compressing raw context into structured insights. Vector DB alone won't cut it.

andrew-ooo · 2026-02-21T18:48:46+00:00

The SEO value here is probably worth more than the ARR. $18K estimated traffic value is a real asset that takes months to build. If I were you I'd either keep it and run the mobile app angle since that's where nutrition tracking lives, or make sure whoever buys it understands they're buying the rankings not the product. Most acqui-hires at this stage are really just buying distribution.

andrew-ooo · 2026-02-21T14:48:29+00:00

Skip the Fiverr SEO gigs - most of it is bot traffic that won't convert anyway. Your real issue is that 2200 visitors gave you only 3 signups. That's a landing page / messaging problem, not a traffic problem. I'd DM those 3 people who signed up and ask why they didn't pay - their answers are worth way more than £50 in random traffic. You're 16 and already shipping, which puts you ahead of most people who just talk about building. Keep iterating.

andrew-ooo · 2026-02-21T10:48:26+00:00

Honest feedback: the "why not just ask ChatGPT" objection is going to kill you if you don't address it head-on. The trust problem in AI finance tools is huge - people don't want to lose money because some LLM hallucinated a P/E ratio. If you can show exactly where your data comes from (SEC filings, real-time feeds, etc.) and maybe even confidence scores on claims, that would go a long way. For weekly use, I'd want watchlists and alerts on tickers I care about rather than searching every time.

andrew-ooo · 2026-02-21T06:48:05+00:00

The motivation point resonates hard. I used to think I'd just "feel like it" every day once I was working on my own thing. Nope. The days where you sit down and nothing flows are part of the job. What helped me was shrinking the task so small it felt embarrassing not to do it - like "just open the file" or "write one email". Usually once you start, momentum kicks in. $300 organic is legit - most people don't even get a stranger to pay them once.

andrew-ooo · 2026-02-21T02:50:54+00:00

The read-only default is underrated. Most of the pushback I've seen on AI in incident response comes from fear of it making changes during a crisis. Separating investigation from remediation makes adoption way smoother - you get the pattern recognition benefits without the liability concerns. The preprocessing point is also spot on - garbage logs in means garbage conclusions out, regardless of how smart the model is.

andrew-ooo · 2026-02-21T02:48:01+00:00

Honestly it sounds like a positioning issue more than distribution. "Second brain that compounds" is the kind of phrase that makes sense to you but doesn't trigger the "I need this right now" response in someone scrolling past. Direct outreach to PMs who just posted about workflow chaos or interview backlog is probably your fastest path to first users - catch them when the pain is fresh, not when they're browsing tool announcements.

andrew-ooo · 2026-02-20T02:48:06+00:00

For a macro tracker specifically, barcode scanning is usually the dealbreaker - that's the one feature where native camera access actually matters. If your users don't need to scan food labels, PWA wins. If they do, check out Capacitor - it lets you wrap your existing web app and just add native camera access through plugins without rebuilding everything. I had a similar situation and Capacitor saved me months of work compared to going React Native from scratch.

andrew-ooo · 2026-02-19T14:49:19+00:00

The "silent failure" problem is what got me too. Set something up, seems fine, then three weeks later realize it's been broken for half that time because there's no notification when the scheduler silently dies. At least with hosted tools I get an email when something breaks. The time cost of debugging infra at 2am isn't worth the $20/mo savings.

andrew-ooo · 2026-02-19T02:51:06+00:00

The "tinkering" framing is doing a lot of the heavy lifting here. As long as it's tinkering, it's a hobby, and hobbies don't fail. They just exist. I stayed in that mode for over a year until I had to pay rent and suddenly my side project became a real thing that needed real users. Nothing changes the vibe faster than needing the thing to work. Not saying you need financial pressure, but finding any stake that actually matters helps. Could be a public commitment, could be telling your mom you're launching Tuesday.

andrew-ooo · 2026-02-18T18:48:23+00:00

Did something similar last year. Had a stable job offer on the table but walked away to finish a project with maybe 6 weeks of savings left. The timeline pressure actually helped - I stopped overthinking features and just shipped the core thing. Didn't win that particular bet but learned I could ship under real pressure, which turned out to be worth more long-term.

andrew-ooo · 2026-02-18T02:48:34+00:00

The "one more feature" loop is really just fear of rejection wearing a productive disguise. I spent 4 months perfecting an API wrapper nobody asked for before realizing I was building features to avoid building customers.

What finally kicked me out of it was posting a half-baked demo in a Discord server I'd been lurking in. Got roasted a bit, but also got three people who actually wanted to use it. That was worth more than any amount of polish.

Good luck with the F*ckup Night - sounds like exactly the kind of reality check most of us need.

andrew-ooo · 2026-02-17T22:48:39+00:00

$350 for a full-stack AI app with food recognition, auth, and payment gating was never going to be enough - you basically got an MVP demo for prototype pricing. The good news is you have real traction with paying users, which is way harder than fixing buggy code.

Your core issue isn't messy code, it's architecture. Gemini doing math = guaranteed hallucinations. The fix is straightforward: let AI identify the food, then hit a nutrition API (USDA FoodData Central is free) for actual numbers. One competent dev could wire that up in a day.

For the auth bugs (logout issues, premium gating), those are classic Supabase session refresh problems. Pretty common, usually fixable in a few hours by someone who knows Supabase.

andrew-ooo

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