My Journey as a Young Entrepreneur: Raw and Uncut.

I recently added an answer to a question on Quora, What is your most memorable founder experience?

My answer was:

Being embarrassed to park my beat up old Volvo 240DL next to the Porsche Cayenne one of my new sales hires was driving. I wasn’t even drawing a salary yet.

This got me thinking about all the memorable experiences I’ve had as an entrepreneur and it prompted me to write this blog post recounting my story, because frankly – the entire process of starting a company is one of the most memorable things you will ever do.

I didn’t set out originally to found an internet company. It happened in a roundabout way.

My first experience as an entrepreneur began at the age of 20, buying and selling designer jeans on ebay. This lasted until I discovered the jeans were of ‘questionable origin’. So much for my career in fashion.

Then I discovered began importing in-dash car DVD players from China and selling them on ebay back in 2006. This ended when I had a large order filled with the wrong (much cheaper) product and I was left holding the bag.

After that, I attempted to start my own boutique mortgage company and after leasing and remodeling office space – I mean literally prying up asbestos floor tiles, repainting, and spending weeks sweating my ass off, I ended up having to hand back the keys to the leasing agent just after the new carpet went in, because I had drained my finances in the process.

I remember walking by a couple weeks later and seeing that she had rented it to a new tenant  (presumably at a higher price: ). She got a free remodel and I learned the concept of making sure I gave a business enough runway. Even at the time, I wasn’t upset. I knew that I had gotten carried away with accent walls and carpet samples, instead of paying attention to the shit that actually mattered.

A few months later I decided that I had it all wrong with my brick and mortar failure, and that I was going to start an online mortgage company. I ordered one copy of Dreamweaver from Craigslist NY (definitely of questionable origin) and I was soon spending 10 hours a day building a website.

When I finally got it up, traffic trickled. Plus I knew NOTHING about SEO and marketing at the time, and I finally decided I just didn’t have the money to compete with the ‘big guys’. Plus begging my one mortgage applicant a week to refinance his house was a little less awesome than I had imagined and a little hard on my self respect.

My next business venture was an awning cleaning company. This idea came via a friend who had just gotten out of the business following a divorce and after buying a used Ford Ranger and spending about a thousand dollars on supplies, I was out visiting local businesses and handing out the 3×5 cards I had printed up at the local Staples.

I remember striking out horribly at my firsts sales attempts. I would sheepishly walk into a business and passively mention that I had a business that cleaned awnings and if they needed theirs cleaned, they should call me. They didn’t call.

This is when I learned one of my most important lessons as an entrepreneur – re-pivot your sales pitch until it works. Luckily for me I am a very strong willed, never give-up type of guy, so pretty soon I was walking in with confidence, wearing the remainder of my ‘designer’ jeans along with a polo shirt – looking very much like a small business owner, and my pitch was more like this:

Hi, I’m Lawrence, I own windnsea awning cleaning. I noticed your awning outside and it’s definitely showing some wear from the smog and the salty coastal rain and I’d love to make it look brand new again – it’s one of the first impressions your customers have of your business. My crew will be in the area this Thursday evening if you’d like to schedule a time.

Boom. Sales. It was that easy. Unfortunately, there was no crew. So, I would show up Thursday after ALL the local businesses had closed and I would pop my hood, connect my floodlights to the inverter, wrestle with 100 feet of hose and a 10 foot ladder, and spend about 45 minutes to clean one awning. You can do the math, I was finishing at sunup, and I had to wake up at a respectable hour to do more sales.

This carried on until I eventually became so burnt out that I abandoned the business altogether. Hell, there had to be an easier way than only getting 3 hours of sleep a day.

I admit to feeling a bit deflated at this point on the whole concept of entrepreneurship. My girlfriend at the time must have felt the same way too because I was soon single and living with mom. :/

After awhile, I sold my truck and used the money to move to Santa Barbabra and live like a college dropout for the summer. I was working as a barback, getting drunk and not knowing what the hell I was going to do in life. It was pretty fun!

But that eventually ran its course and I was back at mom’s feeling like a major loser. But, I was writing goals and I hadn’t given up on my dream. Reality however dictated that I pay my way, so I got a job at a restaurant downtown bussing tables and soon I was promoted to waiter! My increase in pay went solely to Nordstroms so I could at least not look like a loser which made me feel better.

After 6 months or so of this, I decided ‘you know what – fuck it, I am going to follow my passion as a writer!’ And voila, I got lucky and got a writing job. Well – sort of. I was hired as a Chief Blogger for an internet marketing startup.

I loved that job. There were about 8 people in the office and we got to drink beer and watch family guy. I spent most of my time writing ad and landing page copy. After a 10-12 hour day, I would come home and read internet marketing blogs until it was bedtime.

Unfortunately, the CEO didn’t like me and I was soon fired along with a young female web designer – in front of the entire company. I cried – in front of the entire company. I think I cried out of sheer embarrassment. He was a real asshole. As she drove me home, I told her that I was going to start a company and I asked if she would wanted to be my business partner. It was my Jerry Maguire moment. She didn’t think so though, so I was on my own.

I had only worked there for a little over a month, but I definitely knew I liked the culture – both of a small startup, and of internet marketing.

I was borrowing a laptop from the girl I was dating at the time and it wasn’t a very founderly. So, I went to FRY’s Electronics in search of the machine that would make me feel like a proper tech founder.

There were laptops there that would have suited me in the five hundred dollar range, but the one I wanted was around eight hundred. It was like the one the guy who fired me had. It had a big screen and it looked like it meant business. I only had about three grand in the bank, but I bought it anyway because I knew it would make me feel confident in my new venture.

So, I went home and spent the next 8 or 9 days building a website and creating a business model. I developed some landing pages and started an adwords account. When I say I spent 8 or 9 days, I mean days. I would work 18 hours a day, no joke. Sometimes I wouldn’t even sleep. At times, I would get up in the morning and immediately start working, only finally stopping hours later because I had to pee so bad that I couldn’t hold it any longer.

Eventually my friends pried me out of the house for dinner and drinks. Well, after just two moderately strong Belgian beers, I was WASTED. The lack of food and sleep coupled with the fatigue and I was no match for a couple glasses of Chimay. I definitely remember the waitress not liking me at that point.

Anyway, a few days later I began cold calling clients to sell them leads, but my pitch was BAAAD. I don’t even remember how bad, but I couldn’t even keep them on the phone.

But, like I had learned with my awning business, I had to re-pivot my sales pitch. So, pretty soon it was more like this:

Hi, my name is Lawrence Black and I have a boutique internet marketing firm. I generate wholesale leads for other companies to resell, but I’m looking to increase my margins by establishing some direct relationships.

Boom. Sales. Pretty soon, there wasn’t a single question I couldn’t answer. I actually only had to spend about a week doing sales because I soon had buyers for all my volume.

Then I got the call. It was the guy who fired me in front of the whole company. It went something like this: ‘I’m going to fucking bury you! You better watch your back.!..etc.’ He accused me of taking proprietary information, but it was totally untrue. I didn’t take a single keyword or client. Although I sure as hell could have.

(I really suspect he was just threatened on some personal ego related level, which I also suspect is why he fired me in the first place – but that’s neither here nor there.)

Anyway, then I got the letter from his massive downtown law firm and I had a meltdown. I thought it was over. Thankfully, I consulted an attorney at the recommendation of a friend. He reviewed the letter, told me it had no legs, made one phone call to the other attorney and that was squashed.

I continued running the business and working like crazy. I had no CRM at the time to send out leads, so I had to individually email them and manually keep track of what clients got which leads. But, my bottom line was going up and to the right. Things were good.

I began receiving calls from referrals and pretty soon I got a call that changed the game. It was another lead shop and they wanted to meet with me. So, I took a cab down to the local Rock Bottom to meet with their CEO and one of his managers.

Unlike myself, the title suited him. He had the top of the line Lexus, the 5 million dollar home, the high paid managers and the sales staff. He was a real CEO.

He said that he was impressed with what I was doing and he wanted to work with me. To cut to the chase, I ended up partnering with him about 6 weeks later. I bought a beater Volvo 240DL to commute to our new office and we worked our asses off.

I would often stay till midnight or later. Between my leads and his clients, we were putting up some pretty good numbers. My laptop incubated business soon had a handful of employees and even though they all drove nicer cars then I did, I felt in awe of what was going on.

Unfortunately discrepancies in our accounting practices eventually ended our business partnership. As I’ve learned since, this is what a lot of partnerships tend to do, they get messy. My attorney had warned me beforehand but I didn’t listen. My former partner is a great guy and I was very fortunate to work with him, but it just didn’t work out.

Before I knew it, I gave him back his clients and I left the big baller office. I was sitting back at my mom’s kitchen table with my laptop. But, it didn’t take long for me to get on my Blackberry and establish a fairly decent passive income for myself that lasted another solid year.

However, things eventually wound down as the marketplace became over-saturated. Click costs went up while the market pushed the prices down.

I wrote about some of the other factors that contributed to this business no longer being viable for me in a post entitled: Lessons from My Previous Business.

I am thankful that I have derived benefit from every experience I have had as an entrepreneur. Studying Journalism after high school made me a great copywriter. Trying to build an online mortgage company gave me valuable web development experience. My awning cleaning business made me a good salesperson. Working at an internet marketing startup opened the door to a new opportunity. Founding my last business gave me a incredible amount of experience.

I’m more prepared then ever to crush it and I’m presently getting ready for my next and hopefully most significant journey. Stay hungry my friends.

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