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What we would've done differently in the first year of bootstrapping our company (foundersconfidential418.substack.com)
55 points by DtNZNkLN 54 days ago | hide | past | favorite | 16 comments



> Unfortunately, a lot of this compliance stuff is really confusing. To make matters worse, there is shockingly little good information out there to help you through it. If any accountant, tax specialist, or business backend process expert of any kind is reading this: There is an SEO goldmine waiting for you if you write clear, step-by-step instructions for compliance stuff for bootstrapped C-corps.

Won't LLM businesses steal this SEO attempt in an instant?

More likely, keep that know-how as a black box service, maybe with some IT automation.

For advertising that with SEO, you could make the SEO text LLM-aware, and lean harder on not just providing enough information for someone reading it to think "these people seem to know what they're talking about; I should give them my business", but crafting the article in such a way that the desired conclusion is preserved in the output of the robo-plagiarist.


I can't help but feel that is pushing another SEO turtle on the stack. There's always another rung of SEO bottom-feeder trying to steal your thunder, I feel like.


> This experience allowed us to set a clear focus for the next phase of our roadmap: No More Martins.

If you decide either that you owe it to Martin to help him succeed, and/or you want other people like Martin to succeed... you could dedicate a team of some of your best people to high-touch determine whatever is required to help Martin specifically to succeed. Validating it with the success of the original Martin. (Preferably constraining the approaches to things that might conceivably scale. But if necessary doing things that you initially don't see how to scale.)

Instead of roadmap phase "No More Martins", it could be "No Martin Left Behind", "Martin Tiger Team", "360 Degree Martin Experience", or "Martin of Oz".


Because we're just 2 people, the only team we have is us :) That's why whatever our focus is becomes the next phase of our roadmap.


If your product actually does what it claims and somehow Duolingo English test was an important requirement to get a job, won't some Tiktok videos about people who are successful because of your platform catch fire immediately?

I worry a lot of these "what we learned" posts sidestep the real issue: the problem being solved isn't really that big of a deal to most people or it doesn't actually solve it in a measurably better way.


I really wonder about spending time on #1.Content Marketing in the new age of search + AI.

Most searches are filled with large paragraphs of AI responses at the very top of the page now days.

Then everyone doing content marketing is using the same AI to spew out massive spam sites of worthless content.


Content marketing isn't just about search. It's about putting things out that people want to read, or want to share, or use as a reference, with their general awareness of your site coming alongside that. Sure, if it's SEO'd that can be nice, but SEO is competitive - really good content often isn't, especially when that content comes from your own unique areas of expertise.

Our blog's been on the front page here twice in the last two months. Once [1] was me posting, but the posted blog did not directly pitch my company at all - it was just an interesting retrospective about what I learned at my last one. The other blog post [2] was explicitly about us, but it was posted organically (I was actually asleep at the time and woke up to a bunch of slack alerts). Neither has been searched for very much, nor do I expect they will be in the near future - but they did bring in hundreds of signups and a dozen high-intent inbound calls, which is more than enough to make them successful from a marketing perspective.

For comparison, a decent client call would take many, many hours of manual outreach, meaning that each of those posts was the equivalent of months of grindy, spammy, demoralizing labor on my part even if we set aside all the engineers they brought in.

[1] https://news.ycombinator.com/item?id=40634774

[2] https://news.ycombinator.com/item?id=40901224


What it seems like you are specifically talking about is advertising? Content marketing is just having the right collateral in the right channel at the right time, this can be as simple as making sure you have stickers at a meetup. SEO the way we did it at DigitalOcean is probably still possible (that is high quality tutorials about relevant tech), but that is an expensive undertaking and you have to ride it out if you're going to do it (+ find someone like Etel Sverdlov).


It might impact top of funnel (visits), but quality content will really stand out once visitors are at your site, which should increase conversion rate. Regardless, quality content is important for branding/perceived reputation, which is going to be helpful.

It's easier to stand out when everyone goes crappy and cheap. This won't change.


lol, a website is not a good way to promote a business for most startups. Even a YT, facebook, or linkedin page will generate better lead volume.

The nonexistent brand recognition means most SEO and online advertising is a waste of time and money. i.e. random users are usually not going to suddenly discover your products and services in significant volumes.

Mostly we would see around 2400 new users after each contextually relevant community event, 400 per trade-show, and around 25 per informal business gathering.

To match similar lead volume on the web, it would take about 8 months to reach the same volumes as a single community event. i.e. random browsers are generally not going to investigate unknown brands unless they were tipped off by another user. You will see that exponential curve initially as early adopters share their experience with friends, and more users investigate the "free tier".

That exponential growth also requires persistent release updates (extinction rate is about 5 months), monitoring customer feedback, and keeping your profit mode traction quiet. However, do not rely on people stepping up to help out on any vanity project, and plan 2 month release cycles around your core use-case for paying customers.

The key to survival as a company is cash flow in the front door, and providing value to customers. Unless you can do both, than form a nonprofit instead.

Note, every castle needs a moat with legal alligators... If the product/service technological barrier is too low, than a competitor in a better brand position will scoop the market your team cultivated.

As a startup your chances are 1:22, and even lower if you are not objectively studying other firms founding years. Not the success stories, but rather the 21 other firms that didn't win the launch lottery.

As a side note, entering a market already saturated with crap is usually economically unfeasible. The goodwill available with consumers has been burned already.

Best of luck, =3


Not a founder at the moment, but I do purchase a lot of b2b SaaS/infra services. Usually I hear of the brand first, but really high quality content is one factor that makes me decide between competitors. That’s all I meant.


Makes sense for small firms to run low entry cost subscriptions at first, but make sure to build a spreadsheet calculator to regularly project costs. Note accumulating variable costs can pack a wallop during growth, and external services EOL all the time.

Anecdotally, we found aesthetically focused firms lived up to the old adage:

"If you can't dazzle them with brilliance, baffle them with bullshit." ( W.C. Fields )

Best of luck, =3


Funnily enough, all the crap out there makes useful content more valuable, not less.

Sometimes it's harder to find on Google now, but people still need it, so if you can create it and help them find it, they will be grateful. And grateful people will take out their wallets.


I could not agree more with this. I think as the quantity of content increases, quality content will only increase in value.


Time to invest in non-AI content


I just seems to me that the problem is market fit. If you are finding it hard to get people to sign up, then maybe you are tackling the wrong problem or framing the product in the wrong way.




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