What 160 entrepreneurs wish they knew BEFORE they started their business.

What 160 entrepreneurs wish they knew BEFORE they started their business.

I recently stumbled upon this great Twitter post:

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Something about this post resonated with people, and it received over 160 replies from people that have left the safety of a job and started their own business.

While I was reading through the replies, I noticed that most of the advice that was being given was amazing! There was a whole lot of advice that I wish I knew before starting a business. It would have saved me both time and money!

The problem with Twitter is that this post will disappear into the social media abyss within a few days, never to be seen again.

But this was informational gold, and I wanted to dig it up.

So, I’ve cherry-picked the best replies and have categorised them into mindset, financial, lifestyle, practical and productivity.

Enjoy, and let me know in the comments if you have any tips to add to the list.


  • The mental battle you will play in your mind as weeks and months of working harder than you ever did before with 0 pay is much more difficult on you than might have imagined
  • I thought the jump from bi-weekly paychecks to working for myself was a leap off the cliff. When I did it, it was a short hop. Wish I had realized that sooner. If you have the drive to try on your own you can always go back to a job if you have to.
  • Managing your emotional state is just as/if not more important than your actual daily work.
  • It’ll probably take 2-3x longer than you think it will to pay yourself. The emotional rollercoaster is real. Expect to battle the Trough of Sorrow. Tune out opinions from anyone who hasn’t met with you at least 3 times to discuss your startup in-depth.
  • That there are options to start with zero capital, just a laptop and an internet connection. Market your skillset and you can be positive in month 1.
  • You suffer more in your imaginations than in reality.
  • Why I didn’t start sooner Best advice was don’t wait to think it all through – you can always backfill anything you didn’t think of Analyze your Strengths, Weaknesses Opptys and Threats and away you go 25 yrs later still going.
  • Be hyper-focused on solving one small problem. Quitting your job is a super overwhelming experience, you need a North Star that drives direction every day. Don’t make the same mistakes I did, paralysis by over-analysis.
  • You’ll have to tear yourself down and build yourself back up from scratch to survive. And it’s gonna feel like shit. Every day. And you’ll never stop questioning if this is the right thing for you to be doing. You can’t be prepared for it. You just have to go through it.
  • That doing well enough is worse than failing. You might be making enough to get by but then all your free time is gone, vacations are all working, and you are generally stuck on a treadmill. Once on it, you lose all perspective since your just trying to keep up.
  • Higher highs, lower lows. Also, when you have no boss or bureaucracy to blame, know the level of self-scrutiny will be intense.
  • That I could have done it soooo long ago if I changed my mindset, invested in my skillset and set the bar for being in my inner circle as those who fed my faith and fund of knowledge instead of my fear.
  • To know that the journey is soooo much more challenging than you can ever imagine. And to highly reconsider taking that leap before you have a consistent customer/subscriber base.
  • It’s not as scary as you think and you’ll get so many more opportunities than you expect.
  • How much better life would be. I should have started my business years ago. I was scared.
  • I wish I knew that “Business and startups are not for lazy people”.


  • Know your bookwork, tax situation and deductions you can take advantage of by starting your gig. Then follow your gut, your heart, and your passion and never look back! There are always people telling you that you will fail…prove them wrong.
  • Health Insurance – scary no matter how you slice it. Also wickedly expensive unless you learn to think way outside the box.
  • Make sure to get all your personal borrowing completed. Get your credit limits as high as possible. You’re going into the personal debt desert for a few years. Home loans, student loans and car loans are very difficult once self-employed.
  • Hire a bookkeeper stat.
  • learn more about taxes. $5k from your job is not the same as $5k from the business lol. go get an accountant/bookkeeper/tax guy as well 🙂
  • Establish accounting systems and procedures for personal finances to be more familiar with how you want to operate business accounting systems.
  • To figure out a personal cash flow plan first for personal expenses. Living on saving for X months? Consulting for cashflow? Work 10-15 hours? What’s the plan so personal expenses don’t cross with business needs.
  • Go all in. Incorporate because it’ll make you look more credible, you’ll have more protections in case anything unexpected were to happen, and the fringe benefits are better when it comes to taxes compared to freelancing.
  • learn about taxes and get on top of bookkeeping asap.
  • Hire a good accountant. Keep a record of any transaction in writing. Consistency is key.
  • Plan personal financial needs for the next 3-4 years. Money gets spent faster than you think. Business traction comes later than you think.
  • You might spend all your savings trying to build the business. Try to maintain savings, not everything can be bought and not everything advertised is worth buying. Spend judiciously and it’s not as hard as everyone says it is.
  • Allocate a % of your salary towards investment into your startup whilst you have security.
  • How big a deal admin tasks end up being. being organized in-office is critical.
  • Never leave for something that doesn’t cover your monthly expenses.
  • Choosing the right set of clients, being patient, financial management.
  • Don’t save on hiring a decent accountant, spend the money. Getting a good one will save you a lot of pain. Especially if you are financially illiterate like me.


  • Don’t expect family to inherently support or believe in you – will set yourself for disappointment If they do, awesome If they don’t, it’s okay and you don’t need to PROVE them wrong Just diff risk tolerance/goals
  • I knew this instinctually, but make sure your spouse understands exactly what it’s going to be like for years to come (ups/downs, 24/7) etc.
  • Keep your vital energy high (exercises, sleep, diet, positive mindset).
  • The 1st year will suck. Grit through it. Take advantage of the extra time you’re not a job to do revenue moving things (not junk work).
  • Find balance. Going all-in means fighting doubt and fear. Kitesurfing helps me stay positive.


  • That I’d be working way more on my business(es) than I did on the 9-5, that working for self requires immense discipline and desire to succeed and also that to scale you need to hire & automate and you should do it before you think you should.
  • Be prepared that things take a lot longer than one would expect.
  • I wish I had started sooner. All the principles behind great content creation also apply to entrepreneurship, with the exception being that you get paid better in the latter lol.
  •  Believe in yourself. Take care of your health. Rome wasn’t built in a day.
  • It’s easier than I thought it would be. I was convinced watching my old company struggle to gain a foothold was normal. Turns out I didn’t care if they grew or not when I didn’t own a piece.
  • There are usually very few instances where it’s a good idea to 100% quit and devote 100% to the new business. After you quit you HAVE to make the business work – does this mean premature scale? Other risks? Keep an income and start the biz.
  • Spend time b4 leaving getting organized in personal life – do the little chores you never bothered doing like backing up hard drives, getting Global Entry, updating DMV regs, spending QT w f&f – make sure as much of your life is on autopilot as possible. Then hang on it’s a blur!
  • And one more thing. Learn to say no. My first few years were insane. It’s difficult when first starting, but get yourself to a point where you work with people you like. Saying no is a superpower.
  • Clients come in waves. Two weeks of no calls or emails, and then you’re so busy you’re scheduling three weeks out and working until 2 AM for 6 days straight. The quiet weeks are for growing.


  • Save up 6 months of runway (depletes twice as fast as you think). don’t quit but instead, reduce hours to two days a week to cover basic expenses. Build your business four days a week. Build a business that requires little to no cash investment but instead needs your time, graft, and smarts
  • Get the paperwork done for LLC (PTY LTD), trademarks, logos, local licenses and permits in parallel with your job. They take time and you don’t need a lot of attention while continuing on the job. Don’t sign up for long term leases and contracts if you aim to grow. Grow balls of steel resilience.
  • Hire help sooner. Esp areas where you are not as strong (or where you get bored). Focus on your strengths. 
  • It’s going to take a lot longer to get where you want. Build a savings buffer. Also, you don’t have to quit to do your biz – run both until the biz makes more money than the job.
  • Small-business / startup dynamics are very different from corporate ones. Partners, suppliers and clients will behave differently when you are a small business as opposed to a Fortune 500 company. Sounds obvious but I’ve learned it’s a common mistake.
  • Don’t work for free-thinking you are doing so to develop a relationship and don’t work on the come (ie for a success fee). Too many variables outside of your control. Get paid market for your time.
  • That it would take 10 years to achieve the goal 🙂
  • Most of what you read will deter you not to starting an SMB because you will not meet the requirements. You don’t need as much capital as you think. Know & track ALL your #’s. Think unconventionally. Stay persistent. Keel your word.
  • If you are doing B2B, try to get your first customer before you start your business. This way you have a steady flow of money from the beginning. It’s much harder if you plan to spend years on developing a product/service before you can start billing.
  • Make 10X the effort and do it way sooner
  • Learn high level about all the things you need to do to run a business that isn’t connected to what you actually “do”. Marketing, sales, ops, finances but then be very selective of the few key areas you’re going to focus on in each. You can’t do it all.
  • Don’t sell only when you need work. That’s a mistake I made. I was constantly chasing the ball. Always market, always sell.
  • That a good idea on its own is not enough. You also need knowledge, strategy and execution.

I’ve edited a couple of the replies for spelling and grammar, but if you want to read the full post, you can check it out here

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