Bootstrapped Entrepreneur Netting 7 Figures @ 25 - Q&A

I get PM every day or so here asking questions so I figure might as well answer questions publicly to maximize value for the community. Happy to verify if a mod PMs but my post should be pretty telling.

Preface for what it's like starting out.

Keep in mind this is for true entrepreneurship and not some bullshit small business.

  • Get ready to essentially burn thousands of hours making very little until you get good. Think of it as an education. I was probably making the equivalent of like $10 an hour for a long time. Even with "good" income purely because of hours worked. If you're in banking you shouldn't have any issue with the hours but you will likely not be particularly big on the idea of working 1000/2500+ hours on an idea before finding out it's worthless.

  • For years my daily consisted of taking opiates/gabapentin/etc... with adderall to counteract the sleepiness. This let me cold call 8 - 10 hours a day successfully and then complete the work after that. You probably don't need the drugs but just be ready to live like absolute shit for a while. You don't have to do that but if you want to make real money quickly then you need to go all in and burn everything else. I'm pretty healthy now, workout 2x a day, no drugs other than fun ones, but I also do much less taxing work that I find more enjoyable and less grindy,

  • Weird super stressful shit happens frequently. IE I had to give rape counselling to a female employee and I was like...23. I don't know anything about rape or rape counselling. Super weird and not something I really wanted to get weighed down with when I was dealing with the stress of operating a company but that's just part of it. You'll also deal with black swan events both good and bad. Oh and the black swans that are good usually come with some scaling pain. :)

  • It's really, really stressful. If you're not stressed out you're not moving fast enough or working hard enough. Eventually you'll find nothing really stresses you out though. I got "lucky" because my chronic pain condition I was diagnosed with at 17 made other things way less stressful. I don't have to deal with it now which has given me a lot to be grateful and also nothing really stresses me out now. People tell me I look relaxed all the time but...it's just because I'm happy I don't feel like someone stabbed me 43 times 24/7 .

Approach to building new companies/core recommendations:

  • Make extremely asymmetric bets at first so failure isn't a huge deal and won't bankrupt you. Get GREAT at microtesting. Being able to test ideas without heavy expenditure is a skill that will last you a lifetime and transfers into anything.

  • Do not build a product you want but do build a product that solves your problems if they are big enough and are actually problems other people have. It's VERY easy to conduct basic research/polls for free using forums/reddit/etc...

  • Use preorders and partner with big influencers if you're short cash. This is what I did. Took a fuck ton of cold emails but...it works. If you're posting here, you're probably smart enough to write a good cold email. Look up copywriting basics before you do it.

  • Focus on building beautiful scalable systems with low capex. Capex can come later once your idea is proven. IE starting a physical store is a shit idea because you're locked into a lease. Manufacturing yourself is a shitty idea because you're dumping cash into equipment before you prove out demand. This is also because I think like a marketer so YMMV.

  • If you don't have huge amounts of cash don't play the pricing game. I never price "competitively" because a big boy could wipe me out overnight due to their war chest being bigger and their sheer size overall. IMO it's better to have an amazing brand with a reputation for quality and price at a premium. Suit Supply can't just offer a $10,000 suit and knock isaia out of business, can they? :) Brands create huge EV as well.

  • Optimize for profitability and not scale unless you're in tech. Fuck selling equity. Companies in eComm/D2C are largely sold on EBITDA multiples unless you are MASSIVE. Plus you want that cash flow ASAP as you can reinvest it and reap the power of your money compounding.

  • Exits are overrated. Where are you going to invest that cash anyways if you don't have solid deal flow or the knowledge to invest it correctly anyways? Most entrepreneurs fucking suck at that and burn their cash on shitty deals after an exit and end up working for a PE fund as an operator, which is cool and all, but you're an entrepreneur to avoid working for others so.... My approach = exit if I get offering an amazing multiple or see a better opp but in the interim I'm happy to buy, create and hold great companies and then use the cash flow to invest and get better and better at that. Wealth management is an underrated skill and hiring wealth managers is a pretty shitty idea. They're not rich for a reason and GS will just rape you anyways.

  • As soon as you have the revenue requirements passed, join EO/YPO. Expensive but great networking opportunities and I've met some awesome people through it.

Background:

  • Ended up with only an 82/85% avg in hs because my last year I ran into severe health problems. By severe I mean a condition bad enough to get scripts for as many painkillers as I wanted so I ended up at an OKish school. Well respected in Canada but IMO not really worth going to schools without amazing networks or full of legitimately talented A-players like you find @ targets.

  • Hated uni because it was full of retards and was making me more than some of my profs flipping shit on eBay/CL. I was working 80+ hours at this point. Had jobs in sales/etc... too.

  • Built a large online community when FB organic reach was amazing and used that to...flip stuff faster!

  • Leveraged the community to move healthy chunks of custom inventory for retailers and collected a commission. Essentially acting as an affiliate. This is where I made most of my seed cash.

  • Eliminated the middle man and launched our own retail op. Retail op ended up with much lower op margins than I expected. Around 15% or so. Even though we did $1M+ our first year with like $20k into it, it wasn't really worth it because we only paid ourselves like $50k each for 100+ hour work weeks for a year. It also did't scale cleanly. At the same time I was trying my hand at various businesses prior/during the above. One took off I was just VP/consultant.

  • Started an offshoot of the main retail op that did really well. Like 15k in and $500k+ in EBITDA first year and tracking $1M+ EBITDA second year.

  • Started investing in various consumer brands and eComm retailers where I can add value. This allows me to buy in dirt cheap because of operating experience. Typical deals look like a royalty on revenue + salary cap on founders + good equity chunks for me. I invest PE style and not like an angel/VC as PE style returns are way way way better in my size range + cash flow is immediate so I can reinvest super fast. Even if the operators are shit I make my money back in under 6 - 15 months because of the royalty and the salary cap on operators. Largest co will do $10M+.

I also sometimes start companies and throw $25k - $75k at starting them if I find good talent and we have an idea we want to test/launch. IE I have a supplement co. we are about to do this with ATM.

Day to day:

  • I could stop working if I wanted to but I'd get super bored. Absolutely love working with smart people in a variety of fields and industries all day. The other day I talked to an ex-data scientist from Uber about leveraging her knowledge to optimize product sorting/merchandising for one of our larger retail ops and then an iBanker about organizing a small divi recap for one of our companies, which requires creativity because you don't usually see divi recaps on companies with under $5M EBITDA. Usually I put in 80 - 100 hour weeks.

  • Daily work looks like calls in the morning for the company I still operate day-to-day (sort of?). I'm not big on operating although this company is growing too fast to risk handing to someone greener than me so I do it. It still only works out to 5 -15 hours a week. More during product launches/rehauling core systems. IE if marketing needs to be audited and double checked for efficacy then I'm the one doing it.

  • Been spending most of my time building channels for deal flow and talking to/meeting operators. This has been immensely useful to me as it's given me perspective you can't get anywhere else on how different business models function and work. Plus anything I really like about a business I take and integrate into my portfolio companies.

  • Spend time a few times a week helping operators in my portfolio with their various issues. One company needed debt quickly for inventory so I helped them raise $250k in PIK bonds overnight from other companies and friends.

  • Working on a strategy to start buying up bigger companies. Starting a fund makes no sense because the math doesn't work out in terms of returns for myself.

 

I have a couple questions for you as I have always had an interest in eCommerce.

  1. Are the days of finding a underutilized product on fba, buying said product on Alibaba and listing on amazon over? Is this still profitable?

  2. If someone that was completely new to eCommerce wanted to make 500 a month what would you tell them to do?

 
  1. It's much much more competitive than it used to be but I'm not really into Amazon and never have been. I know a lot about it and the guy running marketplaces for me used to work for a VC listing 1m+ SKUs a month but even he hates the fact Amazon treats sellers like shit. Also you don't really build a defensible brand or real EV that way. Maybe a fun side project but not really a real business IMO.

  2. It depends on what they're good at and what their hobbies are. Kind of tough to answer.

 

So would you say building a brand is the way to go in the eCommerce world vs finding under priced items to sell on amazon?

It seems like the payout for building a brand would be much higher but then you also have to account for more marketing, storing your product, and website creation etc.(correct me if i'm wrong).

Idea generation.....How do you do it? I know everyone says solve a problem your'e having but that doesn't help my personal idea generation very much. Do you have any old examples you can share?

 

If you're coming up with original, custom products and designs, how do you deal with knockoffs showing up and eating into your margin? Chinese sellers are particularly adept at copying a product at lightning speed. And it's very difficult to enforce trademark or patent rights.

Does not selling on Amazon or eBay protect you to a degree from copycats?

 

It's not a problem because like you said, we don't rely on Amazon or feEbay for anything. Are they channels?

Yes, but they don't drive the bulk of any of my businesses.

Plus we are selling very band heavy mid/high end products. Broke people can't afford our products anyways. It's kind of like assuming Isaia has to worry about Suit Supply or IndoChino. Two totally different audiences if that makes sense?

To give you a great example I had a company I exited last year and it sold cosmetics. Each product was ~$25 USD when "competitors" are $5 - $7. People buying our products are not going to go out and buy Chinese made cosmetics. People even looking at our products in the first place are not going to buy Chinese cosmetics. We manufacture in the US and have a crazy marketing setup that some random Chinese copycat co. will never be able to replicate because I bought all the influencers in the space and created a bullet proof moat.

 

Thanks, that's helpful and appreciate the example. How do you come up with your niches to target? It seems like you've had success across multiple categories and you probably didn't start out as an expert in all of them (e.g. cosmetics). Are you looking at things like category gross margins, undermonetized influencers, etc to guide towards what to go after?

 

In your experience, what are some of the most successful types of products in this high end eCommerce niche? Is it mostly fashion, cosmetics, etc.? What do you think about luxury handmade goods? 

 

I bought all the influencers in the space and created a bullet proof moat.

Hey, I'm interested in starting my own D2C brand and I found this point interesting. Hope I'm not too late on the thread. I'm wondering how did you find these influencers and how did you know they were good fits to market your product?

 

Were you solo in this or did you have a Partner? When you ran into obstacles, what or who was your main source of advisory/mentorship/guidance?

For example, surely once you began to scale, you would want to hire or partner with an accountant. At what stages did you begin engaging/consulting with other professionals to help in your business, if any?

 

I've had various partners, none I'd want to keep long term until I met the guys I work with now on the investment side but we still use our own capital and our own entities.

Re: professionals. As soon as I could afford them really. The gap is the fucking worst though. By gap I mean the gap between being able to afford good talent and having to do things yourself/with semi-decent employees.

 

As an accountant (CPA), I'm curious how you handled the accounting as the company developed. Did you start recording transactions/budgeting in Excel? Upgrade to Quickbooks, then eventually hire an external accountant?

Appreciate if you could walk through the various stages and share your experience with the accounting aspect of entrepreneurship.

 

When did you know you wanted to be an entrepreneur and did you make the jump before or after you had your first idea? I have always wanted to jump ship, but let be honest, the idea of abandoning the track I have set up for myself and going into the complete unknown is incredibly daunting.

 

Any forums/podcasts/websites you'd recommend for someone that is trying to do the same thing as you on a smaller scale? Any good road maps on the web that will get us going in the right direction?

 
Most Helpful

To start:

E-Myth Mastery: The Seven Essential Disciplines for Building a World Class Company ^ for systems

Principles: Life and Work Dalio, Ray

Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist Feld, Brad

The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers Horowitz, Ben

All Marketers are Liars: The Underground Classic That Explains How Marketing Really Works--and Why Authenticity Is the Best Marketing of All Godin, Seth

The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success Thorndike, William N.

Mergers and Acquisitions from A to Z Sherman, Andrew J.

Getting More: How to Negotiate to Achieve Your Goals in the Real World Diamond, Stuart

The Brand Flip: Why customers now run companies and how to profit from it Neumeier, Marty

Purple Cow, New Edition: Transform Your Business by Being Remarkable Godin, Seth

SPIN Selling Rackham, Neil

The Personal MBA: Master the Art of Business Kaufman, Josh

 

Thanks for the write up. Very cool story

Just have 3 questions:

  1. What is your objective with influencer? To provide advertisement? Would you send them a free product to endorse and give them a % of your sales in exchange?

  2. Where/how do you source PE deals?

  3. Do you believe technology/software related companies are the best to bootstrap? Seemly because the cost is low (no inventory), and you can quickly rollout your idea for testing

 
  1. Driving visitors to your website or physical store is always one of the biggest costs in a business. A good influencer can significantly reduce that cost. Depends on the deal. I'm partners with one right now and he has equity. Usually though, they just get a cut of sales + flat fee or just one of those.

  2. Stupid amounts of networking and we currently send out roughly 200 - 250 emails a week.

  3. Depends on the business... A marketplace startup like eBay would require a huge userbase before the primary value is unlocked. Can't have a marketplace without users and getting users = $$$.

 

Great stuff!. Love this post. Your core recommendations are so spot on. I particularly enjoyed reading the first few:

Build a product that solves a problem, not one you like : Sooooo many entrepreneurs fall in live with their product / solution that everyone has to have. They fail to see that no one really cares yet they pour their soles in to it (and their cash). That's why 90% fail.

Micro test - key. You can't afford big, drawn out losses until you have scale, and youc an't afford to build scale. You need quick small wins. Every day, win. That builds up cash which allows you to invest in new opportunities (distribution, R/D, etc.)

Don't worry about scale and exits - There are basically two types of very successful models, 1. Low margin scaled business 2. High margin, unique client experience business

Way too many people try to start a Scaled, high margin, unique experience business. They go away quickly because the truly scaled businesses can put squash them in a second.

Really good post!

 

m_1 this is a great post and I've probably asked you a million questions. One thing I think people could really benefit from if you care to share is how to choose a product......I've heard of various methods all the way from inventing something new, to taking an existing product and making it a little better. For someone that's just starting out I would be curious to see what you recommend?

 

It depends immensely on so many factors that it's hard to recommend a specific approach. If you check out Purple Cow, I think it's honestly an amazing guide to product creation. Seth has always been way way way ahead of his time.

If you're just starting out, I would recommend making a product in an industry you're familiar with or something you're passionate about/a hardcore user of. Try to stay away from anything too R&D heavy if you can't convince a manufacturer to eat costs for you.

 

I've also been opportunistically flipping things on eBay and Craigslist. I've love to get to a point where I could captain my own ship full time.

It seems like the flavor of recent years has been in selling courses as a $997 course can prove to be VERY profitable. Have you considered selling courses, what is your take on that part of the industry? Think Tai Lopez, Sam Owens etc.

 

Flipping is great easy cash and a pretty safe way to build up some capital to invest in starting a more scalable business. Good call!

Re: IM guys...

I respect those guys as the brilliant internet marketers they are and one of my friends is the ex-CMO for a huge infoproduct guy and I know his current CEO too but... I don't think it creates real wealth long term personally.

 

At the end of the day for them those aren't long term sustainable businesses but gimmicky sales schemes.. Thanks again.

I'd love to learn how you got into the cosmetic business. I was thinking about this the other day seeing how successful Kylie Jenner has been (granted she has an unbelievable reach given her family brand, it just had me thinking...)

 

Fantastic post, thank you m_1

I used to run old school landing pages to with affiliate links buried in copy with keywords for the search engines. It was short-lived, but the dudes who trekked on and made it big (guys on WarriorForum, TheVault) made an absolute killing.

In modern day, looks like you're killing it man! My question would be when it comes to building a brand, what's your bread and butter? You mention Instagram Influencers, but I'm curious if you do AdWords, Facebook, YouTube or other.

My father does what you do full-time and has been self-employed for the past 10 years and like you, he doesn't deal with business partners. Must be an IM guy thing ;)

 

Well, I have partners for every business but my issue has been getting them to scale with the business properly. This is because they are all from my first batch though when I was greener. The guys I do the PE style deals with are essentially partners and I love working with them. They actually work real hours as well and we are total personality matches.

How you build a brand really depends on the industry, the approach is different for every industry. I aim to basically show how our products are better on the quality end and then sheer hype as well + a feeling of exclusivity for customers. My main focus is always on delivering a great product but also an amazing experience overall. For example, when you buy some of our products, you usually get a nice hand written note with it and access to a special VIP CS #, etc...

Re: channels, we aim for diversification as it's always bad to rely on one channel as a matter of practicality but also EV. We go very very heavy on FB + AdWords + YT and a bit of Bing. Depends on the company/product/industry. Not all companies use influencers. One of my companies is almost entirely AdWords with a ~$2M yearly spend for example.

 
m_1:
What specifically?
Well, you're risking your money and your time (which is money).
  • How do you decide that any particular project is worth an investment?
  • How do you decide when to fold a project?
  • Are there any specific red flags that get you to "not touch this with a barge pole"?
I have a friend who lives in the country, and it's supposed to be an hour from 42nd Street. A lie! The only thing that's an hour from 42nd Street is 43rd Street!
 

Great post. I am in the tech industry right now and I am planning to start my company as soon as I will have a great idea. However, my point is I am not in a target school with thousands of extremely driven individuals. In my opinion, people are the most important criteria to have a successful start-up. I guess it's also going to be harder to raise funds due to a lack of credibility and track record. I am currently a CS master student and I was thinking to either work for a big tech company or apply for a PhD in a top-school in order to develop a network ?

 

I think you will be better off in working for a big tech company, it'd serve you well and you can build a strong network based from it.

I know a few people who dropped out of their PhD program to start their own companies as well.

No pain no game.
 

I've seen a TON of terrible tech founders with no experience get funded lately. 95% of VCs and angels have no idea what they are doing and are funding absolute trash right now. IMO just go for it while the environment is excellent for raising capital. By the time you finish up it's likely the environment will change.

The easiest way to raise is to approach a local angel association as they are full of inexperienced rich people that truly have no business investing in anything; IE doctors/lawyers putting cash into "AI" deals that are just b-rate machine learning from 10 years ago.

If anyone is interested in just how shitty returns are for VCs, even smaller ones btw, I'd recommend looking up Kauffman Foundation's report on the alpha VCs have generated as of late.

 

Hey m_1,

Thanks for doing this! As I'm sure you can imagine, a lot of guys on these forums probably see "run a business that nets 7 figures a year," and think Oh that's cool but if I make MD one day at my bank I'll make that too lol but they don't really understand the freedom to travel when you want, work as much or as little as you want, and eventually sell the asset a few years down the road (if you want to).

I'm fresh out of UG and have just started my IB analyst gig. I've done a lot of research on AM/online sales and have built out a few funnels myself, so I'm somewhat familiar with the eComm process (no dropshipping though, I want to build my own brand).

My one question is this. If you were working 80-100 hours a week as an IB analyst, how would you find the time to build/work on your business? Would you work on the business while at work when there is downtime, commit 100% of your weekend time to building the business, wake up at 5am and work on it then? Would you consider dropping IB and taking up a more traditional 9-5 job that frees up A LOT of time for you to work on the biz? (thinking enterprise software sales or something similar).

I'm curious to hear your thoughts on this, since I'm sure a lot of people on this forum are in the same boat.

Many thanks man. Have a good week!

 

Thanks for doing the AMA! Very helpful for someone stuck in the idea generation phase. I was wondering what’s your social life like given the amount of success in such young age and what do you do for fun?

 

I have a few hobbies that align with some of my investments but by far my favorite thing to do is deals. I get a huge rush out of putting my own capital at risk and then trying to make the deal work. My primary partners both feel the same way and IMO there's nothing more addictive...and I quit opiates after sustained chronic use the second my chronic pain started going away.

Socially, I don't really gel with anyone my age or even people that are older. I'm extremely good with people (talked the CFO of a household brand into paying me to take $1M+ in IP off them) and I make my money dealing with the qualitative end but really I don't have enough in common with people to talk to them in any meaningful way which is why my only real friends are my close partners I do the investment deals with.

Clubbing/going to bars/parties, etc... is all pointless too. I just get super bored when I could be working on bigger and bigger deals. I automated my dating by hiring someone to manage my profiles which has worked out very well, but it's kind of hard to find girls worth dating that way. Probably going to change that method once I have some time to build out a new system.

 

Thoughts on doing SEO for local businesses (doctors, dentist, chiropractor, plumbers, electricians, roofer, etc...)? If you have a method with semi-automated software (i've found a suite that costs about $2000) that can rank businesses on the first page of google SERPs in these low-medium competition keywords with 100-300 searches per month, do you think you could charge 500-1000/month and just keep repeating...getting more local businesses as clients and just keep growing the monthly revenue stream? I'm thinking of pulling the trigger on the software and making a run as a side business. Curious what your thoughts would be?

just google it...you're welcome
 

Doesn't really scale cleanly and I'm not a fan of relying on Google's search algorithms staying the same for very long. That's why my reputation management business had to burn, was annihilated by Panda just like 98% of that industry.

If you have a real job already in sales/trading, then I would look into something where you know the industry really well, can scale the model, etc... The only reason I had to waste time on businesses that didn't scale cleanly is because I needed the cash. If you need the cash, then yeah, go for it. Do whatever it takes.

 

Hey m_1 great insight into eCom and its related fields. I read every one of your comments; written by a true wizard.

I’m currently in my last year of university and have recently dived head first into the dropshipping waters as I recognise its vast potential. I've not generated sales as of yet as my focus has been on building a very solid knowledge base (e.g. FB advertising, outsourcing, copywriting etc.) — the plan is not to go for small relapsing gains but to hit the ground running and scale to the moon through carefully crafted systems.

If I could so humbly ask: If you were me and capital wasn’t too big an issue (mainly time), what would you be focusing on in the next 365 days?

 

Hi,

Thanks for the AMA. I majored in liberal arts in undergrad and haven't started looking for a job yet. I have a sub-par, full-time job, that I had in undergrad. I want to pursue entrepreneurship but have no capital. Here are the options I'm considering to raise capital; flipping stuff like what you did, go back to school possibly for an msf or cs, or get a better job that pays ok. What do you think I should do?

 

One example off the top of my head; surveying your potential target market is probably your cheapest way of getting market research. You can easily gain access to thousands of people if you just find a subreddit that is highly if not exactly correlated to your idea (i.e - if its clothing related, malefashionadvice has like 1 million users). This in theory should cost you practically nothing other than time spent, and will net you a lot of opinions from people who actually have interest in whatever universe your idea falls under from a consumer perspective.

 

Facebook ads are a great way to do this. You could test a niche or a product with zero R&D investment, or even inventory. Throw up a generic website or sales page, run some traffic to it and see how it converts. Most likely it'll be close to -100% return on ad spend at first, but it should improve as you keep iterating. The business model that I have requires testing a ton of products and within a few hundred bucks in spend I'll know whether or not it scales. I don't spend much more since I'm not heavily invested into the products but if I was and had a unique or patented product, I'd definitely spend more testing before calling it quits.

 

Bump but I have always wondered, how is your company (or holding company) structured? Do you have like a LLC and buy things in that LLC as the holding entity or do you just keep things simple and have everything separate?

 

Your story is so, so, so inspiring and motivating.

I'm not understanding your background though? What did you major in? What degree do you have?

You said you learned all of this from books and trial and error, but a lot of it sounds like very complex shit that you learn in school + working in that niche area for a while.

 

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