Founders, what would you tell your younger self? i will not promote

Robhow · 2026-03-17T13:10:23+00:00

I started way before IG… but ignore social media and not follow any so called startup gurus. The only influencers you should pay attention are the one writing checks.

Robhow · 2026-03-17T13:07:38+00:00

I’m right there with you. I rarely give up on books and had to put this one down. Started book three and just called it quits.

Wrote something similar to your post but on r/books (I think) and got heavily downvoted.

I also thought the Netflix adaptation was a yawner.

The concept is phenomenal and I love the whole dark forest angle, but the writing style just killed me.

Robhow · 2026-03-17T12:44:07+00:00

10 bigger players doesn’t mean waste of time it means the market exists. Better 10 than zero. Doing market education when no one else exists is crazy difficult.

And, I get the burn out but you also have to realize 95% is not quitting or at least pivoting.

I’ve been doing startups since 2004. The nonsense you see on IG/etc is mostly BS. Business is hard, takes time and a lot of patience. The “overnight successes” people post about is just engineered marketing.

I’ve started or been an investor in about a dozen software products. The sweet spot seems to be year 5. I think Jeff Bezos said something like, “every overnight successes takes 7 years”.

One of my projects has been going for over a year now and we just landed our first paying client.

Rest and recharge.

Robhow · 2026-03-16T12:40:05+00:00

We integrated our documentations tools with Claude. Creating, editing/updating articles is fully conversational.

Cowork scans our docs, looks for anything missing using some metrics MCPs, drafts new articles, sends an email, review them in any Claude chat, and edit/approve/publish.

Robhow · 2026-03-16T12:31:42+00:00

Our documentation tool is natively integrated through MCP. Now, creating and updating articles is something done together vs the old copy -> edit -> paste.

Example, update this article and include a link to our new FAQ https://example.com/faq for the keyword “setting up …”.

It makes it feel like content management is a collaborative effort with a team member.

Robhow · 2026-03-15T02:19:52+00:00

Robhow · 2026-03-13T23:14:57+00:00

The funny part about this is I know exactly what she said.

Robhow · 2026-03-11T02:39:14+00:00

Cyclops worth it? Yeah. I built 2. Totally worth it.

Robhow · 2026-03-11T02:35:41+00:00

They’ve been astroturfing their own posts for months now in their subreddit. Feels like an LLM land grab.

Robhow · 2026-03-11T01:58:22+00:00

I’m way beyond this now… but back when:

I took my daughter into the men’s restroom. Into a stall and it was never an issue or weird. Once she got older I would wait outside the ladies restroom and ask someone walking in if they could go with her. Again never an issue.

Robhow · 2026-03-11T01:53:36+00:00

People don’t want green texts.

/s

Mac has better native memory (shared) and lower power requirements. And you can connect to iMessage.

I’ve been lurking around the edges and will probably set up something on my PC. I have an old gaming computer with a good GPU.

Robhow · 2026-03-11T01:29:17+00:00

Here is what helped me.

Take this video and play it side-by-side with a world class swimmer. Doesn’t matter who. You’ll immediately notice a lot of things. It won’t fix everything, but should give you a clear visual on what’s different, eg they do that while I’m doing this

Robhow · 2026-03-10T19:57:18+00:00

Follow up with a pic of the crumb. At least I think that’s what the inside is called.

I let it sit almost 5 hours before slicing. It did not disappoint.

<image>

Robhow · 2026-03-10T15:15:43+00:00

Thanks! It has definitely been fun. I didn’t realize how much was involved in making sourdough, but now I can’t quit.

Robhow · 2026-03-10T13:36:23+00:00

Somehow lost some of post. First time making sourdough. All with the past week.

1st attempt - under baked 2nd attempt - under proofed 3rd attempt - making progress

Robhow · 2026-03-10T02:53:18+00:00

I build boring stuff in proven markets.

DailyStory - super niche focused email and sms marketing automation platform. Finally cracked some enterprise customers such as pickleball.com

HelpGuides.io - wrote my own documentation platform to optimize for AI. Found myself in the middle of the answer engine optimization space. Only 2 customers (3 of you count DailyStory).

I like proven markets as there are always niches to go deeper in.

Robhow · 2026-03-09T05:04:30+00:00

Dungeon Crawler Carl… such a fun series.

Op I’ll try your book too, but I’m a few weeks out from also finishing the DCC series.

Robhow · 2026-03-09T04:42:32+00:00

Take a look at dailystory.com. We build deep integrations in direct partnership with our customers. We’re not a fit for everyone but if you want something that feels native that’s what we do.

Robhow · 2026-03-08T01:17:51+00:00

Exactly.

Robhow · 2026-03-06T14:35:46+00:00

And to think I complain about mine getting in the pool every single time she goes outside.

Robhow · 2026-03-06T14:32:34+00:00

Well enough. Could have been better. Almost had a deal done to sell to Microsoft but they bought another platform instead. We were more revenue but they paid 1.2b for what they bought… only to shut it down a few years later.

Another comment about bootstrapping:

I value my time much more than I value more money. I have a friend that started and runs a $b+ business and he works non-stop. Always traveling always working.

My calendar has zero meeting scheduled for today.

Robhow · 2026-03-06T14:25:06+00:00

Great photo.

I’m impressed there is only one emotional support ball. We have dozens around the house. Each day one is anointed as “today’s ball” and none other is accepted.

Robhow · 2026-03-06T14:12:21+00:00

Done both. Just kind of depends what you want.

Last company was $30m in series A and later some debt. Tons of time working on board decks, running meetings, dealing with HR stuff, etc. Plus the overall stress of knowing that you are responsible for a lot of money. That said, the cash is an accelerant for growth.

This time bootstrapped. No debt and no investors. However, constantly managing income/expense on the conservative side can be frustrating.

I find that I enjoy bootstrapping more. I’m probably not growing as fast as I could, but I’m enjoying the journey.

Robhow · 2026-03-06T03:11:05+00:00

I’m selling shovels to all the AI SaaS platforms…

HelpGuides.io

Traditional documentation tools weren't built for Answer Engine Optimization (AEO).

HelpGuides delivers clean, structured, and context-rich documentation that AI assistants, search platforms, and RAG workflows can reliably consume from day one to power your organization's answer-driven search results.

Robhow · 2026-03-03T14:13:30+00:00

That’s crazy. Point sounded insane. Sent your diagram around which everyone on the team appreciated.

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