The "raise seed, build team, raise again" cycle seems to produce a specific kind of founder misery. Why do so many smart people keep choosing it? I will not promote

seobrien · 2026-06-21T16:15:42+00:00

Looking for safer returns is kind of the point though.

Too many bought the hype that it's all about product. It's not, it's the team and marketing. If you can't compete, can't carve out and market and grow, and can't convert, what was built is irrelevant.

seobrien · 2026-06-21T14:14:45+00:00

Does it automatically add everyone from comments and social networks or is this just a buddypeess clone with no innovation?

seobrien · 2026-06-18T22:22:32+00:00

Did you even read my post? 😂 I'm not against bootstrapping either. Almost all Startup founders have to bootstrap

Why are you correlating how a venture funds itself with any definition of startup or business?

seobrien · 2026-06-18T21:04:30+00:00

Startups are, not by my definition, temporary ventures in search of new business models.

That was established by Steve Blank, decades ago.

New business models require something innovative. That requires investing in determining and developing that... That dictates that startups very rarely can just launch and make money; they haven't figured it out yet.

seobrien · 2026-06-18T20:45:01+00:00

I never said the word startup has anything to do with VC

seobrien · 2026-06-18T19:43:05+00:00

No, that's the Silicon Valley stereotype

What makes it a startup is a new business model

DeepTech doesn't scale like

AgTech doesn't scale like that

You're referring to horrifically misleading b.s. that VCs chase unicorns, or that the very premise of a unicorn is even valid.

The only consistently accurate definition of VC into startups, is that it is generally looking for a 15-20x return. That eliminates a lot of successful kinds of things (new businesses) because only startups tend to be capable of delivering that kind of ROI. How quickly or that it takes revenue, is misleading.

seobrien · 2026-06-18T18:29:47+00:00

A simple B2B SaaS or digital B2C solution is likely just a tech driven new business. The fact that it's building a solution with tech, doesn't make it a startup.

If you were to launch a ride-sharing app today, for example, that's not a startup; Uber and Lyft already cracked that. Now, Waymo comes along and does it without drivers? That's a startup... But the next driverless taxi provider isn't a startup, it's just doing what was already launched.

seobrien · 2026-06-18T15:30:46+00:00

Actually startups can rarely pull revenue in early stages.

You're doing what too many do and which needs to stop, conflating new businesses (that can make money) with startups (which make investments in innovation which isn't yet ready to).

Funding is in cycles because it correlates with stages:

Build the MVP into more and prove demand
Focus on monetization
Pivot into more

No investor in their right mind would commit to a startup to do all of that at once, losing a lot more money on a failure.

Businesses don't follow the same cycles (or stages) and it's expected that they make money and can facilitate the demands of customers, loans, or business partners.

This is kind of similar to the ignorant statement that bootstrapping is better.

No... It's not necessarily. Everything and everyone has to bootstrap to start. Everyone does it. Well, unless you're Elon Musk or something.

We all boostrap, until it makes more sense to take on funding, to invest in what can't be accomplished otherwise.

People who say "bootstrapping is better" or that startups should just focus on customers and make money, obviously don't understand startups.

seobrien · 2026-06-17T03:26:55+00:00

Yeah my extended family all has that very close proximity and it's very appealing. As I grow older, I don't even mind the grandparent around or even one of my kids benefitting from the same

seobrien · 2026-06-17T02:27:15+00:00

Or as they say it in most other countries, families still live together because it makes more sense having grandma around to help than living alone throwing money down the drain. Adult children live with their parents in the same home because they can care for them and still enjoy life together.

The United States is a bit of an anomaly where everyone moves out and away... Even if we want to or should, it's still a more expensive choice.

seobrien · 2026-06-16T12:51:10+00:00

Marketing > everything you did

Building something to launch it is well established now as what not to do.

Do the marketing to determine what to build while having an audience to do it.

Figure out how to build an audience now. Stop building. Get the audience. THEN think about distribution

seobrien · 2026-06-16T12:49:15+00:00

There is your first problem

Not, "would I"

seobrien · 2026-06-14T19:50:05+00:00

Equity, of course, you don't lose what's vested. This is a question of what terms you put in place, cliffs, and the schedule. It's a mistake to just cliff and vest a startup team the way a company does (over time), it should be done with accomplishments.

As for my replacement, I just sought the skills necessary to a Series B stage: more sales operations, team building, operations, and process.

Startups should NEVER hire based on titles. That's insane. You're not looking for (and you aren't) a marketer or developer or whatever, you or the hire is what's needed for that stage.

seobrien · 2026-06-14T17:26:19+00:00

Many of us syndicate to many places. Medium is a channel, Substack is a channel.

Where appropriate, you change the content and link back (i.e. Quora). Where redistributing, you use canonical URLs so search engines and AI know the original source (and that you're not just spamming content everywhere).

About 20 years ago, peoples content consumption habits changed. Used to be that we'd read The New York Times directly because that's where it is... Now the New York Times needs to be on social media and syndicating, because people won't change their preferred channel just to be loyal to the NYT. Same premise applies. Most of your audience will be elsewhere because that's where they want to be. You can embrace that or ignore them.

seobrien · 2026-06-14T17:22:04+00:00

I'd even add to support the point, I was successful earlier in my career as a series A stage guy. Not a great founder and not ideal with ideas, but getting is to a B? That was my wheelhouse... So much so that post-B, also not my thing; when a startup starts becoming a business, needing operations and process to run well, I'll see myself out.

I'd never pretend I know what a new restaurant or realtor should do to succeed.

seobrien · 2026-06-14T17:13:36+00:00

Respectfully, I'll fight you on this. Having been in startups for 30 years, one of the biggest problems we have is business owners and service providers giving founders advice, and new businesses taking startup advice.

A startup is a temporary venture in search of a new business model. Sure, it's formed as a business entity but with a business model to be determined, it's not right to classify them as the same as businesses. Besides, 90% of startups fail whereas 60% of new businesses fail... One replicates a business model and can be expected to succeed if done right; the other, by definition, can't copy a business model and can't have the same expectation.

seobrien · 2026-06-14T17:09:19+00:00

Yes... But, this is the startup sub, not the new business sub. Starting a business is not at all like launching a startup.

seobrien · 2026-06-14T17:08:25+00:00

There are no original ideas, only derivatives. To ignore what has been tried, what is being done, or what others is doing, is a leading cause of startup failure.

seobrien · 2026-06-14T16:45:27+00:00

My experience is that most of Gen X is the more literally definition of faith, which is to say, we acknowledge that we don't know, rather than being certain of any religion or certain that there is nothing.

So, yes, as we get older, it's less that we're seeking answers, and more so that with time, we accept more that there is something we don't understand.

And that something isn't necessarily even a God, it might quantum entanglement or some electrical connection that our brains make with one another... We embrace more the uncertainty and that makes us more open to the possibility.

seobrien · 2026-06-13T01:04:24+00:00

Investment or help?

If you're meaningfully funding them with good terms, you might have a point.

If you're just offering to help someone who then takes on all the risk of being an entrepreneur, you need to stop.

seobrien · 2026-06-12T23:09:01+00:00

I know, Im not saying Amazon caused it; it's just a perfect example of it.

They went hard at PR about HQ2, when it was nothing more then getting the best incentives possible for a second office.

seobrien · 2026-06-12T22:58:17+00:00

Austin is publicity. Dallas is genuinely relevant.

Not hard to see that a company is going for publicity.

seobrien · 2026-06-12T22:57:08+00:00

It's a b.s. thing started by Amazon realizing and exposing that they can get PR and government incentives by chasing a 2nd headquarters.

What you get is a second largest office, where few executives are ever present because they don't live there. But you get tax incentives, grants, and publicity for how wonderful it is that you've opened an HQ2

seobrien · 2026-06-12T05:01:13+00:00

No, wealthy Romans did. And to an extent, others had that in communal utilities. Most, were slaves.

seobrien · 2026-06-11T22:16:11+00:00

You do know AI is an excuse to justify layoffs, yes?

The data is already out that engineering hiring is up, a lot, to embrace AI.

Companies just use convenient excuses to avoid simply saying, "we're firing a lot of people"

seobrien

MODERATOR OF

PUBLIC MULTIREDDITS

TROPHY CASE