The Startup Odyssey

After a 3.5-year rollercoaster ride through the startup ecosystem - from “garage” phase to Series A shenanigans - I’ve collected more wisdom than a fortune cookie factory. Buckle up, because we’re about to embark on a journey through the startup jungle, armed with nothing but wit, caffeine, and these 30+ nuggets of startup savvy.

Validate Your Idea (Or End Up Selling Ice to Eskimos)

Remember that brilliant app idea you had at 2 AM? The one that would “revolutionize” how people tie their shoelaces? Yeah, pump the brakes. Before you spend months coding the next “Uber for shoelaces,” make sure people actually want it. Talk to potential users, run surveys, or stand on a street corner with a cardboard sign if you have to. Just don’t build something nobody needs - unless you enjoy having a very expensive hobby.

Ego: Check It at the Door (Along with Your Hipster Glasses)

Your startup is not about you. Shocking, I know. It’s about the users. So, leave your ego at the door, along with those ironic vintage suspenders. Your users don’t care if you think neon green is the next big thing in UI design. Listen to them, even if it means sacrificing your dreams of a comic sans logo.

Chase Users, Not Investors (They’re Like Cats - They’ll Come When You Stop Calling)

Investors are like that crush who never texted back in high school. The moment you stop caring, they’ll suddenly find you irresistible. Focus on building a product people love, and before you know it, investors will be sliding into your DMs faster than you can say “pitch deck.”

Hire Doers, Not Talkers (Unless You’re Starting a Debating Club)

In the early stages, you need people who can roll up their sleeves and get stuff done. Save the “thought leaders” and “visionaries” for later. Right now, you need that person who can code, design, and make coffee - preferably all at the same time.

Your Landing Page: Keep It Simple, Stupid

Your first landing page doesn’t need to win design awards. It just needs to exist. Spend an hour on it, tops. Then get back to actually building your product. Remember, Airbnb’s first website looked like it was designed by a five-year-old with a crayon. They turned out okay.

Full-Stack Developers: The Swiss Army Knives of Startups

In the beginning, one full-stack developer is worth their weight in gold (or Bitcoin, if that’s your thing). They’re like the MacGyver of coding - give them a paperclip and some duct tape, and they’ll build you an MVP.

Think Global, Act Local (But Maybe Skip the “Local” Part)

Why limit yourself to dominating the market for left-handed can openers in your hometown when you could corner the global market for ambidextrous potato peelers? Think big from day one!

SEO: Start Yesterday

If you’re not doing SEO, you’re basically whispering your startup’s name into the void of the internet. Start early, or you’ll end up on page 73 of Google, right next to that embarrassing MySpace profile you forgot to delete.

Sell the Sizzle Before the Steak

Talk to users about features before you build them. It’s like a movie trailer - get people excited before you spend millions on CGI dinosaurs that nobody asked for.

The Hug Test: A Foolproof Hiring Strategy

Only hire people you’d want to hug. It’s weird, but it works. If the thought of embracing a potential hire makes you cringe, trust your gut. You’ll be spending more time with these people than your significant other - make sure you actually like them.

Invest in Your Network (Not Crypto)

Put your money where your network is. Invest in your startup friends, not the latest meme coin. Who knows? Your buddy’s “Tinder for plants” might just be the next big thing. And if not, at least you’ll have someone to commiserate with over artisanal coffee.

Tweet Like Your Startup Depends on It (Because It Might)

Twitter isn’t just for witty one-liners and cat memes. It’s your ticket to building a personal brand, connecting with potential users, and occasionally arguing with strangers about tabs vs. spaces. Start tweeting daily - your future self will thank you (or cringe at your old jokes).

Corporates: The Sirens of the Startup World

Big corporations might seem like the answer to all your problems, promising millions of users and buckets of cash. Spoiler alert: they’re not. They’re more like that friend who always says “we should totally hang out” but never follows through. Focus on real users, not corporate promises.

Avoid Shiny Object Syndrome (Looking at You, Crypto)

Remember when everyone and their grandma was launching an ICO? Yeah, don’t be that startup. Stay focused on your mission, even when the next big thing comes along promising lambos and moon landings.

B2B > B2C (Unless You Enjoy Playing the Lottery)

Building a consumer app is like trying to catch lightning in a bottle while riding a unicycle. Sure, it might work, but the odds are about as good as your chances of becoming the next TikTok dance sensation. B2B might not be as sexy, but it pays the bills.

Know When to Fold ‘Em

Sometimes, your startup idea is as dead as MySpace. Don’t drag it out for years like a startup zombie. Give it a year, tops. If it’s not working, it’s time to have a funeral (complete with tasteful startup-themed floral arrangements) and move on.

Tech Conferences: The Las Vegas of Startups

What happens at tech conferences stays at tech conferences - mainly because nothing actually happens. They’re expensive, time-consuming, and full of “thought leaders” who couldn’t lead a horse to water. Save your money for something more useful, like a year’s supply of energy drinks.

Scrum: The Corporate Cosplay of Startups

If your team needs a daily kindergarten-style check-in to get work done, you might have bigger problems. Hire adults who can manage their own time and communicate like grown-ups. Save the scrum for your weekend rugby team.

DIY or Die (Until Product-Market Fit)

Outsourcing in the early days is like ordering takeout when you’re trying to learn to cook. Do everything in-house until you’ve got product-market fit. It might not be pretty, but at least it’ll be authentic (and probably held together with duct tape and hope).

Bootstrap: Because Who Needs Sleep Anyway?

Raising money is like a full-time job, except instead of a paycheck, you get anxiety and a smaller piece of your company. If you can bootstrap, do it. Your future self (and your therapist) will thank you.

The 10-Year Overnight Success

Remember, Rome wasn’t built in a day, and neither was Facebook (despite what “The Social Network” might have you believe). Be prepared for the long haul. It’s a marathon, not a sprint - more like an ultramarathon through a minefield, actually.

Free Tier: The Gateway Drug That Leads Nowhere

Offering a free tier is like opening a all-you-can-eat buffet and hoping people will pay for the premium napkins. Focus on paid users from day one. They’re the ones who’ll give you real feedback (and, you know, actual money).

Price Like You Mean It

Don’t be the dollar store of your industry. Pricing too low attracts users who are more demanding than a toddler in a candy store and less loyal than a cat. Charge what you’re worth - your bank account (and your sanity) will thank you.

Embrace Failure (It’s Your New Best Friend)

Failure in startups is like carbs in a diet - you try to avoid it, but it’s inevitable and sometimes even necessary. Embrace it, learn from it, and maybe even put it on your LinkedIn profile. “Professional Failure Survivor” has a nice ring to it.

Use Boilerplates (Because Life’s Too Short to Reinvent the Wheel)

Don’t waste time building yet another login page from scratch. Use boilerplates and focus on what makes your product unique. Nobody ever became a unicorn because their password reset flow was artisanal and hand-crafted.

Work-Life Balance: It’s Not Just for Corporate Drones

Missing your best friend’s wedding to debug a non-critical issue is not a badge of honor - it’s a one-way ticket to Regretville, population: you. Take time for family and friends. Your startup will survive if you take a day off. Probably.

Build for People You Actually Like

Life’s too short to build products for people you can’t stand. If you find yourself grumbling every time you talk to a user, it might be time to pivot. Building for a community you love turns work into play (well, stressful, high-stakes play, but play nonetheless).

Write Like Your Startup Depends on It (Because It Does)

Whether it’s blogs, tweets, or product descriptions, writing is the Swiss Army knife of startup skills. Practice daily. Who knows? If your startup doesn’t work out, you might have a future as the next J.K. Rowling of tech twitter.

Data: Your North Star (But Don’t Stare Directly at It)

Data should guide your decisions, not make them for you. It’s like GPS - incredibly useful, but if it tells you to drive into a lake, maybe don’t. Always pair data with common sense and user feedback.

Customer Support: Your Secret Weapon

In the early days, everyone should do customer support. It’s like being a spy in your own product. You’ll learn more from one angry email than from a hundred compliments. Plus, it’s cheaper than therapy (for you and the customer).

Pivot: The Startup Two-Step

Sometimes, your original idea is just the opening act. Be ready to pivot faster than a politician during election season. Your “Uber for goldfish” might evolve into the next big thing in underwater logistics. Stay flexible!

Remember, the startup world is a wild ride - part rollercoaster, part marathon, part circus. But armed with these nuggets of wisdom, you’re ready to face whatever the startup gods throw your way. Now go forth and disrupt something!

P.S. If all else fails, there’s always the option of becoming a professional startup advisor. After all, those who can’t do, teach, right? (Just kidding - please don’t come after me, startup gurus!)

Cheers,

Sim