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What Most Startups Get Wrong (And How to Get It Right)

The Goal Isn't to be Perfect It's to Fail Fast, Fail Early, and Get Going Again

Author

Gregory Kennedy
August 18, 2025

I am (Still) Having a Party (For Founders) in SF

Yes, investors are invited as well.

We are getting close to capacity. Space is limited.

Two Silicon Valley legends have agreed to join me and my co-host, Arjun Dev Arora, for an invite-only and founder-friendly event at TechCrunch Disrupt on Tuesday, October 28, in San Francisco.

Who else is going to be there?

If you’re a founder or VC who would like to attend, reach out. Or apply to participate on the Luma page here.

Drinks are on Paul Xue from Spacestation Labs LTD.

What Most Startups Get Wrong (And How to Get It Right)

I recently received this email:

“I'd particularly appreciate insights on common pitfalls to avoid in the early stages.”

Perfect timing, because I've been thinking about all the spectacular ways I've watched brilliant founders torpedo their own companies. And trust me, I've been part of some abysmal failures over the years.

Here are the biggest mistakes I keep seeing founders make, and how to avoid them:

What They Got Wrong: Building an F1-Grade Datacenter When They Just Needed a Honda

I once saw founders spend vast sums of money on an expensive backend, which included a full build-out of a water-cooled supercomputer at a data center. They worried nonstop about scalability and enforced strict security protocols on their precious system that had, well, zero users. The real kicker for me was that once they spent all the money on equipment, there was little left for user acquisition. Oops.

The lesson:

Just because you're a world-class backend engineer doesn't mean you should build a world-class backend on day one. Your job isn't to showcase your technical skills. It's to figure out if anyone wants to pay for your solution. Save the advanced systems architecture for when you have proof that people will use it.

What They Got Wrong: Chasing New Tech Trends Instead of Building Something People Wanted

We all know a founder who pivoted from the metaverse to blockchain to AI and back to blockchain, and now their site says "AI-powered Web3 blockchain solutions.” Their Asana is a graveyard of half-finished projects, and their pitch deck changed more often than a teenager's Instagram bio. They spent so much time chasing the next big thing that they never stopped to think, “What problem am I solving and for whom?”

The lesson: 

Pick one problem that people have right now, and stick with it long enough to solve it. Yes, AI is exciting. Yes, stablecoins might change the world. But you know what's more exciting? Building something people will pay money for today. Tech trends come and go, but scaling your ARR is the most exciting trend you will ever be a part of.

What They Got Wrong: Holding Out for FAANG-Stars When They Just Needed A-Players

This drove me nuts. I was at one place where we burned way too many cycles trying to recruit people from FAANG companies. The founder turned down capable people because they hadn't worked at a prestigious company, or the BD person couldn’t get through their engineering puzzles interview (My blood is boiling thinking about this now). Meanwhile, competitors ran circles around us and stole our lead.

The lesson: 

You don't need MrBeast to make a decent YouTube video. You need people who can ship a quality product and won't quit the moment they get a better offer. A motivated developer who cares about your mission will outperform a bored senior engineer every damn time. Recruit MrBeast when you're making MrBeast-level money.

What They Got Wrong: Building Their Dream Product Instead of Their Customer's Dream Product

Reddit/SaaS is full of stories of founders who spent 18 months building the "perfect" app because they were frustrated with some other app. They added every feature they wanted, custom workflows, advanced reporting, and integration with 107 other apps. But when they launch, it’s crickets. Many times, it turns out their specific problems weren't the same problems shared by others.

The lesson:

Just because you're annoyed by something doesn't mean thousands of other people also are. Before you build anything, validate it. Find 50 people who have the problem you think you're solving and ask them how they currently deal with it. If they're not actively looking for a solution or paying money for terrible alternatives, you might be solving a problem that doesn't really exist.

What They Got Wrong: Trying to Bootstrap in a Competitive Market with Venture-Backed Unicorns

If you’re smart and lucky enough to have a hit product, you will attract competitors. If those competitors raise $50M and hire entire teams to build features and spend lavishly on tradeshows, you’re in trouble. But the bootstrapper usually doesn’t realize this because they are too proud of the scrappy approach. That is, until the market crowns a winner, and it wasn't them.

The lesson: 

You need lots of ammunition to win the war. If you're in a market where well-funded competitors can outspend you 100-to-1 on development and marketing, bootstrapping isn't noble. It's naive. Don’t be a fool. There's a time for staying lean and a time to raise a war chest and compete. Don't let pride in "bootstrapping" become the reason you get left in the dust by companies that understand how to scale faster than you.

Fail Fast, Fail Early, Fail Often, and Win More

This just scratches the surface. I could write an entire book on this topic.

Maybe I will.

Here's what I wish someone had told me about startups. You're going to make mistakes. It doesn’t matter how many newsletters you read or Peter Thiel videos you watch. The pressure, the uncertainty, the constant need to decide with incomplete information. There is no way around it. It’s hard.

Remember that the goal isn't to be perfect. It's to fail fast and early, so when you do mess up, you can fix it before it kills your company. Successful startups are just the ones that survived their own mistakes long enough to figure it out.

010 The Gregory and Paul Show - Elon Beef With Altman, Perplexity Buys Chrome? AI Capex

On the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is debating this week.

On this episode, Gregory dials in from LA, Paul unpacks the rise of “vibe marketing,” and the duo debates Elon’s feud with Sam Altman, Perplexity’s Chrome bid, and whether AI CapEx spending is holding up the entire world economy.

Free Vibe Your SaaS Resources

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  • "Every marketing channel sucks right now": 19 unconventional Vibe Marketing ideas that Founders can harness. Get the free presentation →

  • 30-Day SaaS Growth Plan Template: Designed for technical founders who’d rather be building. Get the free eBook →

  • How to get your first 1,000 followers on 𝕏: Building a large following on 𝕏 in 2025 is still possible. Get the free eBook →

  • VC Pitch Deck Templates for Founders: Based on the legendary Sequoia deck, built for real fundraising. Get the free templates →

One Month of Vibe Your SaaS Will Cost You Less Than a Failed Ad Campaign

In fact, I never start with advertising.

I will start with who you’re targeting, why you’re targeting them, and why what you offer them is something they want to buy.

Founders are all good at building, but marketing? It’s an enigma, wrapped in a riddle.

  • I help founders get their sales and marketing sh*t together.

  • Sometimes the pipeline grows fast. Sometimes it doesn’t.

  • But every time we stop posting LinkedIn broems (poems for bros).

If you sign up with Vibe Your SaaS, this is what happens.

  • You will stop sounding like someone who listened to too many a16z podcasts.

  • I will help keep you accountable so you get ‘all the things' done.

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What does it cost?

Get access to my founder-friendly micro-frational CMO service for $1,500/month.

No contracts. No commitements. No BS. Quit anytime.

(Eveyone renews. But why get locked in? What I learned is that founders hate that and love flexibility.)

About Me

I'm Gregory Kennedy, former creative director, 3X head of marketing, and founder of Vibe Your SaaS. I help early-stage startups build real momentum with strategic clarity, AI-driven execution, and zero BS. I love coffee. I love to ride a bike. And I love helping early-stage tech companies win.

Greogry Kennedy // Vibe Your SaaS // www.vbmrktr.com

003 Vibe Your SaaS Playlist - Weekend in L.A.

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