16 Things I Wish I Knew Before Starting a Business

At 24 my friend Sam and I quit our high-paying consulting jobs to build an internet startup, without knowing the first thing about starting a business.

Since then it’s been a ride — we launched Uptrends.ai, raised half-a-million from angel investors, grew to tens of thousands of users, ran out of money, pivoted to Babbl Labs, raised a VC round, signed 5+ hedge fund clients this year already, and (ironically) became a startup instructor.

And while I do subscribe to the Phil Knight “just do it” mentality (there’s never a perfect time), in hindsight there are many many things I wish I’d known before all this — things that would’ve probably saved me lots of time and headaches.

Here are the top 16 things I’ve learned over the past 4 years that I wish I could go back in time to share with my younger pre-startup self:

#1: Business = people pay you $$ to solve their problems

• That’s it, read that again. Nothing else matters.

• It’s worth the reminder because despite being so obvious, many early founders pay more attention to useless vanity metrics (sign-ups, views, likes, etc.) and forget to actually make money until it’s too late. Some waste years trying to build solutions to non-existent problems. This was me.

• Before you worry about anything else (business name, website, incorporation, whatever) your #1 job is to validate that someone is willing to pay you $$ to solve a particular problem for them. Until you’ve done this, the rest is worthless.

• Ideally, they will pay you up front to build it. If you can’t get upfront commitment in cash, get it in writing. If you can’t do either, stop what you’re doing now and find another business (this will be painful yes, but less-so than wasting more time on an inevitable failure)

#2: If you listen, the market will tell you what it wants

• It’s rare to find product-market-fit on your 1st attempt. Accept this.

• Find hope in the fact that if you simply listen to your target customers and keep incrementally validating/invalidating your hypotheses about them enough time, you’ll get where you want to be. Do lots of customer discovery interviews (here)

• There are levels to product-market fit validation: 1) customer has a problem, 2) customer knows they have the problem, 3) is actively seeking a solution, 4) has built a DIY/interim solution, 5) has/can acquire budget.

• In short, build painkillers, not vitamins. Ideally, painkillers for big problems in big markets, for B2B customers who have budgets. Start with one problem for one customer before trialing to boil the ocean, niche is better to start.

#3: A CEO must see (and motivate) the future

• As CEO you will do a bit of everything. It can feel like your job is to be glue - you put out fires, keep the train moving, jack of all trades.

• While these may be true, above everything else, your job as a CEO is to paint the picture of the future. Convince the world (and yourself) that this new future urgently awaits, and that you will bend reality to achieve it.

• More so, this means inspiring and motivating your team, customers, investors, and stakeholders to believe you can do what hasn’t been done. When we started, I thought this was just a made-for-the-movies thing that Steve Jobs did; if we hired good people they’d motivate themselves, right?

• The deeper I get the more I realize that this is actually the critical job of the CEO. Your job is to push a sense of urgency, to demand it, to exemplify it from the top down. Without this any organization (no matter how big or small) grinds to the productive equivalent of a DMV. (CC: Frank Slootman)

#4: Prioritize climbing mountains, not rocks

• Many early founders confuse busyness with productivity. You should spend most of your time solving the big, mission-critical problems, not small ones.

• Think of your priorities from first principles. Zooming all the way out, the top priorities for a CEO generally fall under

  1. Runway - things that keep you from running out of money

  2. Sales - things that help you make more money

  3. Product - things that people pay you money for

• Don’t overcomplicate or lose sight of the top priorities, in this exact order. Sometimes you will forget - I like to use a weekly planner and outline the things that matter most each Monday morning. My rule of thumb: no small potatoes.

#5: Cultivate a cracked team & build in-house

• The ideal founding team IMO is generally 2-3 people, at least 50% technical. This will vary, but generally you need 1+ who can build (write code) and 1+ who can sell. A hacker and a hustler. And they should eat nails for breakfast.

• Outside the founders, you should strive hire only the best, most-cracked team. Do mission-critical processes in-house (outsourcing critical dev / product work to agencies is generally bad and expensive unfortunately)

• Hiring the best means you must excel at recruiting (#4 comes into play here). When you interview, look for motivation and agency first, not necessarily specific skills (ex: Python proficiency, cold-calling experience)

• Be slow to hire and fast to fire. Set clear expectations and incentives up front, and prune when things aren’t working out. Don’t forget to show outward appreciation / reward hard work and exceptional performance

#6: Surround yourself with amazing advisors

• Good advisors will pay dividends. Where you lack expertise, experience, or connection, hire an advisor.

• Early on it’s hard to afford a lot of killer talent / experience on the payroll. A great hack is to create a killer advisor board. Ideally folks who know the industry and have tons of experience & connections. Pay them in equity + commissions.

• My 2-cents is that it’s better to hire an advisor who is interested in being relatively involved (ie. working in the business 10+ hours per month for you) vs. ‘figurehead’ advisors who look good on paper (unless it’s Mark freakin’ Cuban).

• Many early founders underutilize advisors because they’re scared of giving away equity. Okay, sure.. but for the right advisor, a little equity (0.5-1.5%) an easy price to pay. Just be weary of sketchy characters (as in life generally) and set good incentives — I wrote more on advisors here

#7: Outsource everything else

• Anything non-mission critical CAN and SHOULD be outsourced

• The logic is simple: payroll will generally be the biggest expense. So don’t hire people unless you can’t live without them. In theory a small, cracked team + a few seasoned advisors can do 10x the work. Ways to outsource:

  • Partners: work with other companies on joint products / services, outsource the things you aren’t good at to them and share reveue

  • Contractors: hire specialized talent for specific projects without the commitment, temporary and overseas are even better

  • Automation: doing the job with AI counts as outsourcing, too. Use tools like Zapier, ChatGPT, (I wrote about Zapier sales automations here)

• We spent WAY too much on contractors early on, including $5K/month on someone to write tweets for us. Pure insanity when I look back. What were we thinking? We weren't. TBH probably just trying to spend all that investor money to look busy.

#8: Momentum and insanity are both moats

• As with any good business idea, people love to ask “why hasn’t this been done before”. The answer is often one of two things: either no one was moving fast enough, or no one was crazy enough to try

• Momentum is a moat. When you’re small, your superpower is speed. You can ship features in days that would take the big behemoths months. Use this to your advantage !

• Insanity is a moat. Most rational people aren’t crazy enough to try the things you’re attempting. Next time a VC asks you the ‘why hasnt this..’ question tell them this. The more unhinged and unreasonable your vision seems, the fewer competitors you’ll have (ofc assuming there’s market validity)

• We’ve found that our willingness to tackle problems others thought to be too complex / risk is actually one of our biggest advantages (this is part of why #6 cracked team is so important) (CC: Scott Belsky)

#9: Practice strategic procrastination

• The opposite of speed is scope. The great inhibitor of moving fast is scope creep — it truly pains me to say this I once was the scope creep king haha.

• Say no until you absolutely can’t avoid it. Don't build features until customers demand them. Don't hire until you're drowning. Don't spend money on anything until it's painful not to. Don't scale until you've proven product-market fit.

• This isn’t being lazy, it’s being intentional. When investors / users / advisors ask why you haven’t built them something, you get to say “we arent focused on that… yet :-)”. It’s about knowing what NOT to do which is often harder than knowing what TO do.

• Learn to ask “What happens if we dont do this rn?” If the answer isn’t “Business dies” or “We lose critical momentum” then it can probably wait.

#10: Found ways to solve problems yourself

• Avoid unnecessary spending at all costs (I’ll be here all week)

• The best founders are scrappy, resourceful, and clever enough to solve problems without spending a bunch of time or money (this is where being technical helps tremendously, I wrote about this here)

• When we first start, we couldn’t afford a proper cloud compute pipeline for aggregating mass video from YouTube. So we bought a few Mac Mini’s and some old gaming PC’s and built a make-shift server rack in Sam’s apartment. Was it perfect? Hell nooo. Did it land us our first 4 customers? Yes. :-)

• The simple ability to figure things out (code, marketing, sales, legal) will literally save you tens of thousands of $dollars and give you a deeper understanding of your business. (Cutting your teeth is also a moat. #7 automation is key here)

#11: Design processes to stay organize & move faster

• Without proper systems to stay organized you risk descending into chaos.

• You must set intentions for how you will manage tasks, documentation, communication. Create standard operating procedures (SOPs) for repetitive / critical tasks. Use tools like Notion, Granola, and Google Drive to aid you (how I use Notion for startups, and startup communication guide)

• It’s not about bureaucracy, it’s about reducing cognitive load and decision fatigue so you can focus on important things and set clear expectations. In our early days with Uptrends, we wasted months due to inefficient communication, poor documentation, and duplicated work. Now, we don’t :-)

• Remember that processes should evolve as your business does. Bake in quarterly / annual opportunities to review your meeting schedule, doc’s, etc.

#12: Build in public, create community

• The best way to create luck is to put yourself out there, do this by sharing your journey, making introductions, and cultivating connections (how to make warm intros)

• TBH some of our biggest breaks came from random Twitter/LinkedIn DMs, conference hallway conversations , and people who followed our journey online become becoming customer / investors.

• The other great thing about #buildinpublic is that it creates accountability. When you share your goals & progress, you’re generally more likely to follow through. Plus you attract like-minded people by broadcasting your thoughts and journey (the best way to find advisors, employees, investors, customers)

• I’ve probs gotten more value from posting a few blog posts online each week than from all of our paid marketing on Facebook / Google combined.

#13: Be where your target customer is (live inside them)

• Marketing 101: Go where your customers are, understand exactly what they need and why they need it.

• We spent months and thousands of dollars trying to build a following on Twitter/X for Uptrends early on, only to realize that the vast majority of our users simply weren’t using Twitter. We eventually realized 50%+ of paying users were finding us on either Google search or Email - so we quit everything we were doing and focused on building ONLY those channels

• For hedge funds, we realized that our traditional SEO / email marketing weren’t going to work. We need to do things like trade shows and vendor partnerships to meet them where they are. That’s what it’s all about

• It’s a bit of an 80/20 principle here when it comes to marketing. Vast majority of customers will come from a select few channels. Learn their language, understand their problems deeply, and learn how to think like them.

#14: Sell benefits, not products

• To truly sell, it must be about the future benefit, not what you are building. The product is just a vessel.

• When we first pitched our product, we’d talk endlessly about features and technical capabilities. People quickly tune out, or they say “eh thanks but that’s not for me”. Part of this is that people are generally bad at recognizing solutions, but good at seeing problems. When asked about the invention of the automobile, Henry Ford famously said “if I had asked people what they wanted, they would have said faster horses”

• People care about what your solution will do for them. Will it make them more money? Save them time? Make them look good to their boss? Focus on that. (cc: Shaan Puri)

#15: Hire a good lawyer and good accountant

• This just has to be done. Can’t be avoided.

• I’ve heard too many horror stories of founders hiring cheap legal/accounting help (or worse, doing it all with ChatGPT) and having it bite them in the ass later. YES, I know that they can be expensive - you can do first drafts with ChatGPT all you want, but the final say for big decisions with potentially costly mistakes should usually involve a 3rd party professional

• Get attorneys & accountants who specialize in startups. They're worth every penny for the headaches they'll help you avoid. Consider them insurance against existential risks to your business. (If you’re reading this and you need a recommendation, LMK)

#16: Never stop learning, tinkering, reinventing, moving

• Be a shark. If you stop moving, you die.

• The most dangerous thing for any founder is complacency. The moment you think you've figured it all out is the moment someone else is about to eat your lunch.

• The most dangerous thing for any founder is complacency. The moment you think you've figured it all out is the moment you’ve lost. Put yourself out there, learn to fail, fail fast, fail better.

• I call this “increasing your surface area for opportunity” — by constantly learning new skills, exploring adjacent markets, and staying curious, you build a competitive advantage and stay nimble.

So there you have it. The startup journey is a rollercoaster of extreme highs (signing your first Fortune 500 client and committing your first $250K VC check in the same week) and a trial and soul-crushing lows (deciding to layoff your team and sell your business because you’ve ran out of money).

There is no manual, and everyone’s path is different. Hopefully these 16 things will save some future entrepreneur a headache or two, I know some of these things have certainly been a north start for me through the chaos.

Looking back, I ask myself - would I do anything differently? Probably. Would I skip the journey altogether? Not a chance. Often times burning your hand on the stove is the fastest way to learn.

Peace,
Ramsey

PS: Woof, probably my longest blog post ever, hopefully a bit helpful :-) I am writing this from a lanai in Ft Myers, Florida on my first 5-day vacation in a longggggg time