Here is Dan’s takeaways after launching and running four successful companies. He originally shared this on reddit. This is one long post. Hope you find it useful. 

It’s hard to believe it’s been 9 years. But it’s been an epic journey, and as I start my 4th business I have been reflecting a lot. I started writing this for myself as a journal entry of sorts, but thought some of it may be of value to those of you who are just starting out.

But first, a bit about my history.

I have been the founder of 3 companies, and a partner (but not a founder) of one.

  • An 8-figure business
  • A 7-figure business
  • A 6-figure business
  • And you guessed it… A 5-figure business (but it’s not even a week old so it’s doing pretty good!!)

First Company: BizMedia Digital Video Agency did 60k in revenue in the first year, 600k in the second year, and by the third year was a 7figure business from there on out.

Second Company: Vinyl skins for smartphones, laptops, gaming consoles etc. Grew this business to almost an 8-figure business within 3 years before being bought out by the founder (and one of my best friends)

Third Company: Hitsu Socks Online and retail manufacturers of funky socks designed by street artists. An epic journey that had me cycle through 4 different partners until I found my current partner who is an entrepreneur far beyond me who has taken this from a struggling, money losing (but fulfilling) side project into a real business with real legs which is finally a business doing 6-figures. But it was a real grind to find the path with this one. Happy to say it’s on the path to real growth.

And my fourth little baby business: Unbound Merino Only a 5-figure business so far, but like I said it’s only 5 days old, so I think it’s off to a pretty killer start!!

The night after launching my most recent business I couldn’t sleep much. I was very happy with the launch but my head was spinning and I couldn’t stop thinking about all the different experiences I’ve had over the years and how it’s shaped me.

All the people I’ve met and worked with, all the mistakes I’ve made, all the lucky breaks I’ve gotten, and so on and so on. So I started writing some of these things down, not with the intent of sharing them – but more so just to get all the reflections out of my head and on to paper.

Thought maybe it would help me sleep. It did. Anyway – these are some of the lessons of my 9 year journey. It’s not in any particular order and a lot of this is just rambling. But hopefully some of you can take some value from this. And if you have any questions I am happy to answer!

Go save money! It costs a ton of money to start most businesses. You don’t have to be rich to start a company. I was broke as all hell when I started. But I freelanced as a videographer and editor to get the funds to start my first business while waiting tables on the side.

I would rather wait tables and save $20k and start from there than start a business for $500 like a lot of threads I see on here suggest is possible (which it is!). But while you technically CAN start a business with just $500 and be really successful, that is a crazy steep hill to climb.

And getting traction with a $500 startup I am willing to bet would take longer than going and waiting tables, saving $20k and starting with that money. You can always tinker with a $500 startup on the side of making and saving funds working a job.

Forget your social life. It’s not important. It never was and it never will be. Unless of course your social circle is directly related to your line of work / your startup. I mean, people who could help you, work with you, you could sell to, etc.

Just because you went to high school with someone and you like them, doesn’t mean you need to go waste time with them at the bar on Friday nights. Friday night is a time when 95% of the world is taking a break, what a time to get ahead.

If people get mad at you for not coming out any more, tell them you want to focus on your startup. If they can’t understand and support that – you don’t want those people around anyway.

SALES – the most important word in business. Sales is the most important skill you can ever obtain. Good sales people are the most under appreciated and rare breed of people you could ever find. Keep sales people around you.

Go to sales seminars, find entrepreneurs who say the word ‘sales’ over and over again, who’s only concern is sales. They have all the answers you are looking for.

I can’t stress this enough. In business sales fixes every problem. You need to understand the mindset of the people who’s lives are sales. The most successful entrepreneurs have sales blood.

Join and be involved in organizations that better you. I spent years in Toastmasters learning to be a better public speaker, then I joined the board of trade (tried for a year but wasn’t a huge fan), then I joined EO (Entrepreneur’s Organization).

In every year of my journey as an entrepreneur I was a member of, and heavily involved (usually at the board level) in some kind of organization. This is a great way to meet people who are growth oriented and care to see you succeed.

The people you meet in these organizations are the types of friends you want close to you. It may take you a while to find an organization that you take lots of value from, but look for it. And don’t just pay your dues and expect results, put in and contribute.

The more you give, the more you can take out. Being on the board and regional council of EO has been one of the most rewarding experiences of my life and it’s helped me through all of the biggest challenges I’ve faced as an entrepreneur. I don’t know where I would be without the support of the brilliant people in EO Toronto.

Start on something now. While I said go save money before diving in, I didn’t mean you shouldn’t be starting in some capacity. Even if you’re just researching, planning, blogging, maybe doing a side project selling some soap you make at home or something, find something you can make or source, or a service you could provide today – and start selling.

You could be an entrepreneur by tonight if you wanted. All that matters is you have something to sell and you find someone to buy it. Anything. If you get someone to buy something off you, you’re gaining invaluable skills that will compound over time.

Experience is everything. So get started on something, even if you have bigger plans for later. Oh, and if it fails miserably. That’s a great outcome. Which brings me to my next point, and probably the most important…

There is no failure really. Only feedback. That’s a line stolen from Jeffrey Gitomer the sales author. But what the hell is failure really? You tried something and the outcome was different than your hallucination? Failure is FEEDBACK. And it’s the feedback that is only given to those who have the balls to try.

I would rather be a man with 100,000 failures in life than someone who hasn’t tried to do shit. At least I’ll be able to write a book about what not to do at the end of the day. Maybe I’ll have a really sweet reddit post that will get me lots of karma.

OR maybe my experience will take me to the place I was looking for all along. You can look at the list of companies I’ve founded and think I’ve been successful, but I left out all the failures I’ve endured in the process.

The gut wrenching, nightmare inducing fuck ups. But they all help in the end. The key is to never ever let a failure slow you down. Failure will give you that feeling that you need to stop and reconsider your direction.

Just learn from the failures and go harder. The path just becomes clearer and easier to navigate after each failure. As long as you have the will to not let them break you. Feedback. It’s freaking feedback.

Earn Cash, Don’t Burn. Cash Build a business that doesn’t burn cash, but earns cash. It’s so 101, but I’m amazed at how easy it is for people to forget. Don’t spend anything that won’t make you more money in return. Be ruthless about this.

I’ve blown more than $1MIL that I probably didn’t need to over the past 5 years on stupid shit that I am now embarrassed of. And it’s came close to devastating and ending my business.

You don’t need to grow your staff and the size of your office, unless you NEED TO. Stack your money, and guard it. Again, it seems 101 but I admit I have made some pretty dumb decisions spending myself, and so many people around me are guilty of the same thing.

GOALS. I think this will apply to those of you who already have a company, or the early seed of a company. Have a BHAG (big hairy audacious goal – a term from Jim Collins book Good to Great).

A BHAG is a vision of where you can take your business if things go BEYOND WELL and you are incredibly lucky and everything goes amazing, 25 years out.

So if you’re in video you may say you want to create the next HBO or something. Something that is so big that it’s almost unreasonable based off of your reality today. The only reason you need a BHAG is because it sets the direction, no other reason.

From the BHAG, figure out where you could be in 3-5 years if things go well. The 3-5 year goals need to be leading you towards the BHAG. For example, you want to have $10-15MIL in revenue and one online show concept that has XX million subscribers on YouTube and 3-5 corporate sponsors.

I’m just pulling these out of my ass but you get the point. From the 3-5 year goals, find your 1 year goal. Things get real now. What is realistic within 1 year that is in the direction of your 3-5 year goals? Maybe have 5 big corporate video clients (for revenue) but also to have 2 YouTube shows with original content already in production (the early attempts at making big time original content in the future).

AND THIS IS WHERE THE BEST PART COMES IN. The quarterly goals. Nothing is more real than a quarterly goal. 3 months is the perfect amount of time to conquer one meaningful and sizeable project that moves you in the direction or your 1 year goal.

Maybe it’s to have your corporate website up, to have show concepts and pilot scripts written. Whatever. There’s nothing pie in the sky about this. You have 3 months to do it. And it takes you towards your 1 year goal, which is a step towards your 3-5 year goals, which are aimed at your BHAG.

It’s ALL about direction. You can always tweak the long term goals as you go, but the quarterly goals MUST be set in stone and executed against. We break our quarterly goals into weekly and even daily action plans. Take the whole project and map it out over the 3 months and stay on time. Trust the plan. Get in the trenches. Get to work.

Expose yourself to feedback. And let it sting. This really hit home with me recently. My EO forum (group of 8 other entrepreneurs who meet monthly) all recently went on a forum retreat to New York City. We met with another member of EO from a chapter over there.

I am not allowed to share who it was because there are very strict confidentiality rules in place for EO. But, he’s a business titan. He recently sold his company for over $800MIL USD and he took us in and told us all about building his company and what he’s up to now, and took us for lunch and really spent some good time with us.

He’s working on a new project and he was so eager to get our feedback on it. Now it’s important to know that while the businesses in my forum are all multi-million dollar companies, none of us are quite at the level of being sold for $800MIL.

Not even close. But he was so keenly interested in our take on his new business, that it really made me realize that he’s just an obsessive tester. He gets as much info as he can from wherever he can. We may not be as big as him, but we’re all entrepreneurs and that was enough for him to truly want to dig into our thoughts on his direction.

I started being more aggressive in my hunt for feedback on what I do, and it’s amazing to open yourself and your ideas up like that. Even my recent Indiegogo campaign was completely shit on by a few of my colleagues which stung so much.

But ultimately led me to make very pivotal changes last minute that made the campaign way way better. Find mentors, and seek feedback. Be open to what you hear. This may be obvious to some but it took me a while to learn and be more open to it.

If doing business internationally, have a mentor. I do a lot of importing from China and I’ve wasted so much time and money learning lessons the hard way. I then started seeking help from a friends friend who does tons of business in China, and in one hour he taught me enough to completely change the way I get things done with overseas suppliers.

If only I met him earlier, I would have saved SO MUCH FUCKING TIME AND MONEY. If you are dealing with people overseas, find someone to give your pointers and guide you. This actually applies to every aspect of business. But the importing thing is fresh in my mind.

Don’t be an egotistical prick. In your 20’s you are at your peak of energy and there is very little you can do wrong. Fucking up is a gift and the repercussions of doing so in your 20’s are next to nothing. But don’t ever think you’re smarter than those who have been in the game longer.

You may have insights they don’t have because you’re younger – but experience is the best teacher there is. And your ego can easily piss off older people who probably have a ton to teach you and likely would really enjoy helping you. So keep your ego to yourself and surround yourselves with people who are older and wiser than you. And be grateful and have your ears wide open.

You’re the average of the 6 people close to you. If 1 person in your immediate circle isn’t ambitious, hard working, smart, helpful and generally and awesome person… Get them the hell out of your immediate circle. Your close circle is the most important asset you have. Don’t mess it up by having a douche bag in there. Because then you’re 1/6th douche bag yourself.

Passion / Purpose. People always have advice about following your passions, or ignoring you passions to find purpose and yadda yadda yadda. Just fucking learn skills and make each day count. Come up with an idea and a plan and get to work.

There’s nothing wrong with having passions, but I don’t see why everyone tangles passions into your work. I love music, but I don’t need to make my money writing songs about my achy breaky heart or some shit.

I’m happy having music be in my life as I passionately learn and work hard and try to grow my businesses. Learning how to make a business work is just as fun as playing guitar or ice hockey or eating an amazing cheeseburger.

It doesn’t matter if your business is a new social app, or you manufacture industrial cleaning products. The mechanics of starting a company or simply improving yourself are enough to be super passionate about.

I never thought growing up I would be selling socks. I just go through life trying to solve problems and get better every day. So there, my purpose is making each day count towards my longer term goals.

Have an accountant in your circle. Accountants speak the language of business better than anyone else. Have a good one in your corner, and have one as a friend to help you with a second opinion.

Even better, hire one who no longer wants to be an accountant. Have them help you keep your books clean and to mentor you to understand how to really make sense of your P&L. Know your P&L like you know the back of your hand and stay on top of it.

It’s going to get real hard. And when things are the worst, give yourself 5 min to wallow in your own shit and then write down where you want to be, then write down what actions you can do today that would set you in that direction.

You can’t do anything more than what those actions for that day are, so just do that. It’s all you can do. And it’s the right thing to do. Nothing to be bummed out about anymore, you’re doing your best and you’re going in the right direction.

Picking a business to get into. From what I’ve experienced – the best businesses to get into are those where you feel all the current offerings that exist suck. When dbrand was founded, it came from the realization that all the now competitors actually made garbage skins.

For some reason, nobody was doing a good job at making skins. The soil was fertile for that business. My friend started a hair extension business called Luxy Hair. It came from his wifes terrible experience trying to find good quality extensions online for a good price.

They couldn’t find it, so they created it. It’s a multi-million dollar business today. And my new business Unbound, we created it for us (my partners and I), after having no luck finding anything that was the right look, fit and quality. We made this company at a time when the soil is fertile for growth.

My sock business on the other hand was founded in a very crowded market. It took 2 years just to find our niche, and only now are we seeing any traction. We got excited because socks were so popular. That isn’t the smartest time to start a business. It’s a lot tougher.

And lastly…

Entrepreneurship isn’t for everybody. I fell into this and it’s become me. At times being an entrepreneur sucks. Really. I have many days and weeks where I have no idea how I got myself into this. But I am built to handle the shit storm and not break down. Not everyone is like that.

For some people having a good job that you can stop thinking about at 5pm is a much better life. There are amazing upsides to entrepreneurship, but if you aren’t fit for handling the really hard and ugly side, be smart enough to avoid it.

Entrepreneurs have great stories, but you often don’t hear the ones about those who never made a 7 or 8 figure business. There are a lot of casualties in this line of work. And it sucks so bad so often. BUTTTT.

When it doesn’t suck, It’s FUCKING AWESOME!!! Just be ready to not let the feeling of roasting in the fiery ditches of hell with no way out in sight get to you. And when things are great, don’t let that get to you either.