What life lesson did you learn from your first job?

Originally posted on Quora, answering the question: What life lesson did you learn from your first job. Follow me on Quora.

My first job was a dishwasher at popular restaurant in a summer town in New Hampshire. It was the early 90’s. I got paid $2.75 an hour which was the minimum wage. Even though it was a while ago, it was as little as it sounds. In spite of that, it was the most coveted summer job in the town. The owner had every male in the restaurant start as a dishwasher to make sure he had the chops and work ethic to continue (the girls all starter bussing tables).

Busting my ass, working non-stop 8 hours shifts, sorting through an onslaught of food, hot dishes and a steam bath emanating from the dish washer for $2.75 an hour taught me a lot about hard work in the world. The only attitude you could have was to shut up and do your job. We were the absolute lowest people on the totem pole and had to do pretty much anything anyone ranked above us asked. Did I say it was for $2.75 an hour?

Don’t be late. When we started, the owner explained that if we showed up on time (e.g. 8:00 for an 8 AM shift), we were late. That set the precedent in my career to show for jobs up 5–10 minutes early. The right people take notice of that.

Be thorough. The second thing the owner showed us when we got started was a pan. He picked it up and said there wasn’t just one side (e.g. the cooking side) to clean. We cleaned the inside and outside. Sounds trivial, but he had to say it because otherwise it wouldn’t get done.

Help your coworkers. When the restaurant closed, everyone had a list of responsibilities of what they needed to do before they could leave. In theory, you could leave as soon as you wrapped up your work. In practice, everyone who finished their tasks early, chipped in to help everyone else until the work was done. It was unspoken, and I never saw it done otherwise.

Put the effort in. One Sunday morning, I woke to the phone ringing. Before my mom answered, I knew exactly what it was. I hadn’t set my alarm and was an hour late for the early AM shift. I leapt out of bed in a panic, got dressed in 10 seconds without a shower and asked my mom to drive me right away. I was at the restaurant within 10 minutes of them calling. The manager was so stunned I got there so quickly, she cooked me breakfast.

Counter politics with hard work. My first job was also my first exposure to workplace politics. The owner didn’t like me from the start. I smarted off to him a few times and that wasn’t acceptable. However, I was one of the hardest working employees. When work needed to be done, I shut up and put my head down until it was done. He may not of liked me, but his family (also owners) were always impressed by my work and kept an eye out for me.

Respect the boss. Being the boss isn’t easy. The owner worked 14 hour days, 7 days a week from May until September. He was often irritable and rarely in a good mood. I now run my own business. As a manager, boss and/or owner, you have to constantly make difficult decisions. I can’t remember a day where I didn’t have difficult decisions to make. When you’re working for someone else, just know you can’t know the difficulties of what they do until you do it.

Experience trumps all. One of the best lessons of starting working 40 hours a week as a dishwasher at 14 years old was it put me years ahead of work experience of almost everyone I knew. When I moved across the country to Santa Fe after my freshman year in college, I walked into the best restaurant in town and showed up with a full page resume, as a 19 year old. I’d already been working for 5 years. They’d never seen a resume from a 19 year old and hired me on the spot. I run a business now, and there’s simply no replacement for experience. Success in business and leadership requires gaining experience, and experience only comes from work. Summer jobs used to be a rite of passage; recent stats have shown it’s become out of favor. The money I made was trivial, and my parents let me spend it however I wanted; but it was gaining the work experience and learning the work ethic that were the greatest lessons. I don’t know that you need to start when you’re 14, but in an interview for Google when I was 35, they asked about jobs I had in college.

What is the most effective yet efficient way to get rich?

Originally posted on Quora, answering the question: What is the most effective yet efficient way to get rich. Follow me on Quora.


There’s a story of an Italian Billionaire when asked if he had to start over from scratch what he’d do (I searched Google 50 times to find the original without luck). He replied that he’d take any job to make $500, buy a nice suit, then go to parties where he’d meet successful people. The implication being that he meet someone who’d offer him a job, share an opportunity, etc.

I’m almost 40 and of the 5 career type jobs I’ve had in my life (I run my own business now), 4 came through networking. Only 1 came out of applying to a job listing.

But networking isn’t something you just go out and do. It’s immensely more effective if you have simple people skills. And when I say simple, I mean spend a couple hours reading Dale Carnegie’s “How to Win Friends and Influence People.” Read that and try it out at a party and you’ll be blown away by how effective it is and how after meeting and talking with a few people and asking them about themselves, how they’ll want to help you, without you asking them.

When I asked my old boss (who was the most remarkable sales person I’ve met), what he did to improve his sales skills, he told me that right out of college without any skills or pedigree degree, he took a job as a limo driver. He was reading “How to Win Friends and Influence People” and thought it would be worth trying out. He would ask his customers one simple question when they got in the limo, “So tell me about what you do.” That simple question resulted in a huge increase in tips he received. Notice he didn’t ask his customers, “What do you do?” There’s a subtle difference. If you ask the latter, many people will just tell you in a few words what they do. If you ask the former, it’s an invitation for them to tell you their story. Few people will turn that down.

At one point early in my career, I was doing research in the medical field and realized I wasn’t interested in it or where it would lead. I wanted to make more money and get into the business side of things (this was right after the tech crash in the San Francisco area), so I spent nearly 9 months relentlessly applying to jobs, writing cover letters, researching companies. With no success. I was doing it all wrong.

One night, my roommate asked if I wanted to go to a party. Sure, no problem. We went. I didn’t know a single person there. At one point, everyone did shots. I wandered back to the kitchen to get a beer. There was one other guy in the kitchen and I introduced myself. We talked for a while, I asked him what he did and he said he worked in biotech. I mentioned I was looking to get into the field, and he said his company was actually hiring. My resume got sent to the hiring manager, and I was interviewing within a couple weeks. You can guess what my next job was.

There are a million paths to getting rich. And there are countless people who’ve gotten rich who are jerks, tyrants, manipulative, conniving, and all around assholes. When you’re working in different industries, you’ll start to feel that all the  successful people are this way. But in reality, these are only the people who leave the most lasting impression, not because they’re the only people who succeed.

But there’s unlikely anyone out there successful who wouldn’t emphasize the value of people skills in succeeding.

So back to your question, how do you get rich quickly:

The high level:

  1. Learn relentlessly. Read books and books on success, people skills and anything that might have some inkling of a strand of wisdom about success and wealth. Especially read the biographies of successful people. In his autobiography, Mark Cuban talks about how he would buy and read any book on business that he thought might help. The $15 he’d spend was a fraction of the worth of the wisdom he picked up. Drew Houston of Dropbox talks about how he would spend every weekend reading books on business, sales, marketing, all day long. Every weekend.
  2. Become a people person. This is a learnable skill or set of skills. No one is born a great salesperson. There may be people (like athletes) with better inborn abilities (outgoing, etc). But the best learn, read, study, and practice. Relentlessly. A lot of times, those with the best given talent don’t end up being the top in the field because at the start, it came easy to them. The ones that have to work at it, work relentlessly and don’t ever get complacent. And then one morning, they wake up and the effortlessness at sales or marketing or leadership that they never thought they would achieve, they now embody.
  3. Work hard. As an employer, one of the things that stands out the most with employees is a good work ethic. It’s worth its weight in gold. Drop your expectations and ego, and put your nose to the grind and good things will happen.
  4. Take risks. Not dumb, fickle risks and not gambles. But smart, calculated risks where you have a good chance at succeeding. You won’t always succeed, but you will learn a huge amount in the process and you will garner an enormous amount of respect from people in doing so.

The nitty gritty:

  1. Get a job in a high growth industry. This is where the quick money and the opportunities are. There’s a saying how everything rises with the tide. When you’re in a fast growth industry (or company), the tide is rising.
  2. Work for the best and most recognizable company you can work for. This gives you instant credibility. Starting as an intern at a recognizable company will get you opportunities right away.
  3. Become an expert. Pick an area within your industry and learn it inside and out. Start writing answers on the topic in Quora, start a blog on the topic, network with other experts. You’ll find pretty quickly that this type of knowledge and expertise will lead to a huge array of options.
  4. Create multiple income streams. Start writing, consulting, tutoring, fixing things, just get busy with a second source of revenue. This will get you hungry for more and you’ll double your learning. You’ll see that a job, tutoring on the side, can lead to starting your own tutoring company on the side. Your marketing consulting job can lead to writing Amazon books on marketing.
  5. Be too busy to spend money. Feel like you spend too much money? Feel like you don’t save enough or at all? Get busy working on everything, your job, learning, networking, consulting, projects, side jobs, overtime at work and you’ll find out you won’t spend a fraction of the amount of money than before.
  6. Finally, start a company. Name a billionaire who didn’t start a company. Yes, there are a few. But they ended up running the company they joined (Sheryl Sandberg, Steve Ballmer, Eric Schmidt). Starting a company may seem completely out of reach and unfathomable, but when you’ve done all the preceding steps, it will be the most logical next one. Successful companies don’t start out with 50 employees and a $10M in revenue, they start out small, tiny and scrappy. They start out in their dorm rooms or their parents’ garages or spare bedrooms. The founders beg, borrow and steal to get what they need. Michael Dell started his company by hacking together computers in his dorm room and selling them. Walmart started as a single variety store in Newport, Arkansas. Ever hear of Newport, Arkansas? Yeah, me neither. Richard Branson started out selling records by mail, one at a time. Don’t look at the most successful people and companies and see where they ended up or you’ll be overwhelmed. Look where they started and you’ll see how it’s achievable.

How do I become a more interesting person?

Originally posted on Quora, answering the question: How do I become a more interesting person. Follow me on Quora.

“Either write something worth reading about or do something worth writing about” – Ben Franklin

Often easier said than done.

My senior year in high school I sat down for a group interview at a prestigious university. The interviewer asked everyone to share what they did this summer. One girl had spent the summer in London apprenticing under a well known photographer. Another traveled to Italy to study painting. I’d spent the summer in New Hampshire working at an ice cream shop. I didn’t feel the least bit interesting. And becoming interesting sounded very expensive and out of reach.

That’s all changed. Since then I’ve driven across the country 7 times, hitch hiked from San Francisco to LA, attended a Rainbow Family national gathering, backpacked to over 20 different countries among others. I’ve got amazing stories from all of it, but a lot of the best stories didn’t happen because of traveled far or spend a lot of time or money. Here’s what I’ve learned about becoming interesting:

  1. Seek adventure. Adventure doesn’t have to mean traveling to another another country or involving a expensive gear or expenses. One of my most memorable college experiences was hitchhiking from San Francisco to LA. It cost me nothing. I caught somewhere around 10 rides and have a story from each. I’d never hitchhiked before or after. I also took a Greyhound from LA to Santa Fe once and could write a book on all the people I met and stories that happened. The ticket cost me $35. Seeking adventure can be through travel, sports or the outdoors, but it definitely means getting out of your comfort zone.
  2. Be curious. Be curious and learn about the world around you. Read, listen to podcasts, find great websites. Learn from interesting people. Knowledge has never been as accessible as it is now. Knowledge is one of the sources of having interesting things to talk about. You might find an interest in say Astronomy. You could show friends common sites in the night sky and the incredible stories behind them.
  3. Be unconventional. Capturing people’s attention doesn’t have to involve grand stories or adventures, but can come from the unconventional. Triathlons weren’t common right after I got out of school. If you did them then, that’s pretty interesting. Then Team in Training came along (an awesome cause and not taking away anything from it), and suddenly it seemed everyone around me was doing triathlons. Not really that interesting anymore. A friend of mine after college did something no one’s ever done before (at least known). He circumambulated Martha’s Vineyard via its beach/shore. It only took a couple days and some camping gear. 20 years later he still tells the story. He also lived briefly in a Teepee after college. That part is interesting enough. It gets more interesting considering his stay there continued through a cold New Jersey winter. Another friend does long bike tours all over the world (at home in the U.S. as well). That’s pretty interesting. What makes it even more so, is he does it on a beach cruiser.
  4. Delve deeply into a hobby. Interesting people have hobbies they pursue passionately. It’s hard to have more than one or two that you have the time to pursue passionately, but one is all you need. Immersing yourself in hobbies is inherently interesting. You meet other super passionate people, you travel with a purpose and you have shared experiences. I got into scuba diving because I loved the ocean, and I imagined it would be something I did once a year on tropical vacations. I now dive 12-15 times per year in California alone. Primarily off the beaches in Santa Monica and Malibu to hunt for lobster and to spearfish. 50 feet off of beaches packed with tourists, I’ve caught lobster and fish and swum with seals. I bring a camera along to capture it. There’s not a single person I show the photos and video to that isn’t captivated by them and amazed it’s all possible yards off the local beaches.
  5. Explore. I was going to just say “travel,” but exploring is much more interesting. When I was backpacking through Guatemala, taking bus’ around the country and staying on youth hostels, the entire trip was an adventure. A couple approached me. They were on a cruise and were being shepherded around to the touristy sites with hundreds of other people from their cruise. They were amazed and jealous at the freedom I had to see and explore. We were in the same place, they were on a tour and I was exploring. Traveling to Asia, I had an extended layover in Kyoto and hired a taxi driver to take me to the Zen monasteries, he took me to two hugely popular monasteries that although they were beautiful, were immensely crowded and touristy. It didn’t feel like the spirit of Zen at all. I asked him to take me to a quiet monastery. He brought me to one with only a couple other tourists. It had a large beautiful rock garden and empty halls and spaces, and it left a much deeper impression than the touristy ones. I could write pages and pages on this topic, but the key point is to get off the bus, the schedule, the tour and to go explore.
  6. Document and share. It’s much more powerful to show an amazing adventure or trip or experience than it is to try to describe it. I make a habit to document and take great photos of all my trips and to have those photos and videos ready on my phone in albums.
  7. Learn to ask questions and listen. If all you do is talk about yourself and tell stories, you’ll be a huge bore. It won’t matter what you’ve done or where you’ve been, people only really want to hear stories about you to a certain extent, then they want to talk about themselves. Every time I talk about the hobbies or travel, it’s usually a jumping off point to a great conversation where we both share about what interests and fascinates us. You can actually pull this off without having any interesting experiences, just by learning to ask great questions and to listen well. But I wouldn’t recommend bypassing the experiences, because there’s an immeasurable value of actually going out and having these experiences. And it’s not in becoming more interesting, it’s in expanding your perspectives and experiencing the world.

Looking back on that college group interview, I’d felt hugely insecure. I realize now that I was very interesting. In high school, I’d been a student leader and an accomplished athlete. I’d spent my summers working at an ice cream shop and training for road bike racing by riding up to 200 miles per week. It took having all these later experiences to realize that it’s the sense of adventure, passion and curiousity that makes people interesting, not their experiences or where they’ve traveled.

What are the lessons people most often learn too late in life?

Originally posted on Quora, answering the question: What are the lessons people most often learn too late in life. Follow me on Quora.

Learn how to listen. So few people can really listen and so many people genuinely appreciate when you do.

Learn when it’s time to move on. From jobs, people and relationships. Not everything is fixable. Cut your losses and move on.

None of the best experiences of your life will happen staring a computer screen, a phone screen or a TV. If you want more of the best experiences of your life minimize the time you spend in front of these three.

Take great care of your body. It’s delicate and becomes more so as you get older, but if you treat it well, it will treat you well. Exercise regularly, stretch or do yoga, eat wholesome food.

Take great care of your mind. Foster curiosity, read, learn and grow. Learn to be quiet, meditate and spend time in nature regularly.

Take great care of your heart. When you hold onto harmful emotions like anger, hurt, pain, you really only hurt yourself. When you practice love, compassion and generosity, your heart expands and grows.

You’ll spend too much of your life working, staring at a computer screen and sitting. If you’re going to do all these things, find a work environment or shared purpose that’s fulfilling and creates meaning.

Success comes most readily when you find fulfillment and create value in the world.

Learn how to compliment people and do so regularly. There’s no limit on how many compliments you can offer, there’s no scarcity of compliments available and there’s no end to how much people will appreciate them.

Learn how to accept a compliment and do so whenever one is offered. You’re conditioned to deflect compliments. Recognize how you do this and practice recognizing and accepting when the universe acknowledges what you do.

Learn how to be generous. You can’t attract what you don’t give. Share your knowledge, your time, your thoughts, your wisdom, and your charity.

Learn how to be patient. Life is not a race, and it certainly won’t go slower if you rush through everything.

Practice gratitude. If you cultivate gratitude, it has no limit to its rewards and benefits and no cost to nourishing it.

Hard work puts you in the place where luck can find you. The harder you work, the more you help others selflessly, the more value you provide in the world, the luckier you’ll be.

Happiness is a habit, not an aspiration.

Great stories come from great experiences. Chase those experiences.

It’s not that time moves by faster as you get older, you just start to have fewer new and captivating experiences. If you can continue those experiences and expand your curiosity, time won’t feel like it flies by as so commonly described.

What is the most thoughtful/kind act you’ve ever witnessed?

photo-1438027316524-6078d503224bOriginally posted on Quora, answering the question: What is the most thoughtful/kind act you’ve ever witnessed. Follow me on Quora.

After my freshman year in college, I decided to take a year off and live in Santa Fe, New Mexico. My parents were not supportive of my decision, so I had support myself entirely. I worked in restaurants and coffeeshops and was as broke as you could be.

I bought a old junker Volvo. I think I paid $750 (this was 1995). It never ran right from the start, but I couldn’t afford the necessary repairs. It doesn’t seem that long ago, but cars have come a long way. Cars used to regularly break down. Good cars sometime did and newer cars sometimes did. Owning an older used car was a guarantee to inconvenient break downs.

The car’s engine compression was shot. It required rebuilding or replacing the engine which wasn’t an option. It the morning, it wouldn’t start. I lived on a hill and would have to park it there, pointed downhill, so I could do a “hill start.” Letting the car gain momentum on it’s own and then shifting it into gear, which start the engine running.

Unfortunately, there wasn’t always a hill nearby. In those cases, it needed a running start with either myself and someone else pushing it to get it to sufficient speed to start.

This went on for a couple months before the car just died, but in the meantime I was assisted by countless people who would see my hood open, stop and inquire if I needed help. Most didn’t have any inkling of car mechanics, but just felt compelled to help.

It was often a helpless feeling, staring at my car stuck in empty parking lot at night, wondering how I would get home. Inevitably, someone would just pull up and ask if they could help. I was amazed every time someone stopped to help. It was the every rare instance that it did not happen.

Why do charismatic people easily get what they want in life?

Originally posted on Quora, answering the question: Why do charismatic people easily get what they want in life. Follow me on Quora.

Supreme Court Justice, Potter Stewart, once described porn as: hard to define, but “I know it, when I see it.” The same could be said for charisma. It’s hard to define because it takes on many forms through many personalities; but the affects of charisma are always the same: a likability of that person, being drawn to them and a willingness to trust them. With those affects on people, it’s not hard to see why they get what they want in life.

The bigger question is how can the rest of us become more charismatic and get what we want in life as well?

Charisma’s closest cousin in the business world is sales. They’re not one and the same; but great sales people are charismatic, and charismatic people get what they want because people like them and trust them.

Building likability and trust in a very short period of time is the quintessence of sales. What makes sales a great comparison with charisma is that with sales you can break it down to a set of teachable and learnable skills. In fact, that’s what sales programs and books are all about.

The core of sales isn’t talking as it’s often misunderstood, but listening. Great sales people spend most of their time listening and doing so acutely. They’re not distracted, but giving you their whole attention, making you feel interesting and important.

That’s one of the strongest affects charismatic people have. You’ll remember someone who tells a great story, but you’ll remember better someone who makes you feel great. Those are the charismatic people.

There’s a story of a reporter interviewing two candidates for president. After the first interview, she declared “He’s was the most interesting person in Washington!” But after the second interview, she declared of the second candidate “I felt like I was the most interesting person in Washington!”

Great sales people give their full attention and ask great questions. It’s not “So, what do you do?,” but instead “So, tell me about what you do.”

Another characteristic of great sales people is that they’re persuasive.

Persuasiveness starts with agreeing with people. You can’t get people to like you if you’re disagreeing with them, correcting them or trying to be right. No one will remember if you’re right, and you won’t change anyone’s opinion through argument.

People want to be heard, not corrected or challenged. So allow them to be.

I was in a sales presentation to a vice president of top consumer electronics start up. A couple minutes into the meeting, she declared that she didn’t believe in what we did (paying influencers to promote brands and products). In the back of my mind, I thought, “Why, in god’s name, would you ever take this meeting then?!” I had flown up to San Francisco for this meeting and taken precious time from my work week, and now it seemed like a complete waste.

Instead of responding that way, I paused and composed myself. I smiled and responded, “It looks like you’ve done an amazing job marketing your company without having to [pay influencers]…”

She wanted attention and wanted to declare she was different. She also wanted to challenge me and would have gladly gotten into an argument if I had disagreed with her. Getting into an argument is probably the most effective way to ruin a sales meeting. Instead I agreed. Not only did I agree, but I noted that her approach had worked, and that allowed me for the eventual opportunity to be persuasive.

Being persuasive isn’t arguing effectively; it’s not arguing at all.

I asked her to tell me more about how she had created such success without paying influencers to promote their brand and product. She got her chance to talk, which is what she really wanted. Eventually, I brought up the point that many of our current customers were in her same position and shared why they tried our service.

So what are the things can you do to be more charismatic?

  • Smile. You can’t sell in the world and you’ll never be considered charismatic if you’re in a bad mood. People are drawn to people who are in a good mood. Moods are contagious; spread the right one. My friend would do a trick at weddings he’d call “fake wedding table laugh.” At weddings, you’re often seated with a table of strangers. For this trick, he waits for a quiet moment during dinner and then has the whole table laugh out together, loudly. The affect is amazing. Most of the other tables  look with jealously at the table that seems to be having the best time. The fake laugh created a bond and would soon lead to real laughs.
  • Listen. I mean really listen to people. Make strong eye contact and give them your whole presence. Don’t pick up your phone, don’t let your eyes wander around the room. Both are cues that people interpret as you’re not interested in what they’re saying.
  • Tell me more. Use that phrase or something like it during a conversation get all the details out of their story. The details are what will make their story different and are what they want you to remember.
  • Remember the details. I transferred my junior year in high school. Before transferring I was on a visit and saw a play at the new school. The following fall, I ended up meeting the senior class president. He was captain of the soccer and hockey teams. Upon meeting him, I told him excitedly that I saw him in the play last spring and loved his performance. We ended up becoming friends; and years later, he recounted that story and how I stood out for remembering that. Everyone knew him as the athlete and class president, but I made a huge impression on him for noting what most people hadn’t paid attention to. When you see someone after meeting them and recant how their one story really made an impression on you, you will stand out to them.
  • Discover what they love. Everyone has something they’re dying to share and talk about. Often it’s their hobbies, their kids or family, or their job. Almost always, it’s pretty easy to find out what these are. Ask about them and let them share.
  • Talk to everyone you meet. My old boss raised millions of dollars for his biotech company. He met his first investor, who contributed millions of dollars, waiting in a long line to get concert tickets. Most people avoid talking to others throughout the day, at the coffee shop, in line, flying, etc. When you talk to everyone, talking to anyone gets much easier.
  • Agree. Deep down we want to be right, we want to share our opinions and convince others of them. Fight that urge. When people sense disagreement, they put their guard up and prepare to defend their position. You’ll become friends much faster, by agreeing and moving on. Don’t let your opinions get in the way of getting to know someone.
  • Connect. Charismatic people are connected. The world is filled with flakey people. The phrase “let’s grab lunch” is so commonplace, it’s become a way of saying goodbye rather than an actual intention of connecting. Most people crave real connections and have time to grab coffee, so do just that. End the conversation with, “I’d love to hear more and see who I might be able to introduce you too over coffee.” And then actually follow up with them. You build connections and positive relationships.
  • Follow up. After meeting people, send them a note. If just to say you appreciated meeting them. Remind them of what you enjoyed about them or the experience, what inspired you, what you learned. These types of notes are really powerful and will make a huge impression.

I’m unemployed, broke, balding, living with my parents, about to turn 30, friendless, depressed, and miserable. How can I possibly turn it around?

Originally posted on Quora, answering the question: I’m unemployed, broke, balding, living with my parents, about to turn 30, friendless, depressed, and miserable. How can I possibly turn it around. Follow me on Quora.

In 2007, I got laid off from my high paying biotech job and backpacked through Central America. I was 32 at the time. I took all the money I had and bought Apple stock on margin. It was a good year to buy Apple stock as this was the year the iPhone came out. I moved to LA with plans to fulfill my dream of starting a company. I’d always been in interested in tech and the Internet so I started on a solid year of wantrepreneurship.

In 2008, the market came unhinged, the economy experienced the worst recession since the Great Depression and I sold my stock at the bottom, taking huge loses. My start up business hadn’t panned out. I’d made very little progress on my idea, and eventually partnered with a friend to raise money for a Facebook apps company. Neither of us knew a thing about Facebook apps.

What little personal savings I had left was drying up as we started talking to investors. I didn’t have a job and was hoping to raise money to pay the bills and build a company. Then the financial crisis struck. No investors would talk to us. My friend had a job, I was pretty much out of money. By some miracle, unemployment benefits got extended, and I was eligible from having been laid off a year and half earlier. I don’t understand why.

I was now completely broke except for my biweekly unemployment checks which barely covered rent and food. I was 33 year old, hadn’t worked in a year and half and was ostensibly changing careers/industries yet had no experience in the new industry. I was looking for a job as the unemployment rate was rising at rate faster than it had in nearly seventy years. It was a historically bad time to be looking for a job, especially in an industry where I had no experience.

At one point, I couldn’t pay my cellphone bill. I had no idea, but Verizon has a payment plan when you’re back due.

I spent months applying to jobs and writing cover letters. I got coffee and met with anyone and everyone I could. This eventually led to an interview and offer from MySpace (at the time bigger than Facebook and a hot company). I was going to start the following week, then the offer letter got delayed one week. Then another week, then a third. Then MySpace put on a hiring freeze.

I couldn’t pay my credit cards, and creditors were calling non stop. At first I tried to answer the calls, then I just stopped. There wasn’t anything I could do. The news on the economy got worse and worse.

I kept applying to jobs and tried to keep a positive outlook. That was all I could do. My unemployment benefits were about to end. I didn’t know how I was going to pay rent.

A couple weeks before they expired, a friend of friend heard I understood social media and asked me to come in and present to her team. I drafted a strategy for her and presented for a couple hours. I charged $200, a nominal amount but it was a massive boost me for emotionally.

A week or so later, my neighbor on a whim passed on my resume for an open position onto a company where he freelanced. A month later I was head of sales at a top digital Hollywood production company (really the only one of its kind). I felt like I’d won the lottery.

This is just the short version. There were substantially more challenges and adversities I encountered than I’ve listed or have space to.

What I learned:

  • You can only fix one problem at a time. Don’t go out and try to fix your life. Focus and solve only the biggest problem you have. Once you’ve fixed that, move onto the next one. So you’re not bald, broke, unemployed and friendless. You’re just unemployed. Go get a job and you’ve fixed that problem. Then move onto the next.
  • Don’t create new problems for yourself. It doesn’t sound to me like you’d have any problem working in an office job. Are you crippled, maimed or cognitively impaired? No, then you can handle a job. I have to use my left hand for my mouse because of tennis elbow. I don’t think twice about it anymore. Don’t fortune tell problems or scenarios that don’t exist.   As Mark Twain said, “I have known a great many troubles, most of which never happened.”
  • Don’t define yourself by your problems. No ones life is perfect, far from it. Think of who you’d be if you didn’t have your problems. Probably the exact same person. So rediscover who you are and just start over from that point. When I was growing up playing hockey and we were getting whopped by another team, our coach would huddle us together between periods, tell the score was 0-0 and that our job was to win the next period, not the game. The game didn’t seem winnable at this point, but the opposing teams were always caught of guard in the next period by a team they’d mostly counted out. I don’t know that we ever lost a period after those talks, and we came back to win a surprising number of games from a big deficit.
  • Create a routine. You don’t have a job. You’re job now is to get a job. Wake up early, have a morning routine and go somewhere (coffee house etc) where you will work at getting a job for eight hours a day. Now that doesn’t mean writing resumes for that long. It can and should include networking, reading, learning, informational interviews, improving job skills, etc. But create a schedule for yourself. You should make exercise and the outdoors part of the schedule. Research shows that exercise helps alleviate depressions and the NY Times just published an article on another study that shows How Walking in Nature Changes the Brain.
  • Reframe. When I was applying for jobs after being essentially unemployed for 18 months, I listed the 6 months of travel/backpacking I did as “travel sabbatical” on my resume. A director at one of the companies I interviewed at asked about my travels with envy. During my year of wantrepreneurship, I didn’t successfully launch the company I envisioned, but I did learn valuable skills such as blogging, social media, SEO and others. In my interviews, I talked about these skills and my successes, not the fact I couldn’t ultimately raise money and folded the enterprise. Use your time being unemployed, as a chance to learn new job skills, volunteer, pick up a hobby and/or travel. If you don’t think you have the money, a subscription to Lynda runs $25/month. There’s more there to learn than you could possibly cover in a lifetime.
  • Get inspired. You’re far from the first or only one in your predicament. Countless others have overcome difficulties far worse than yours. It can help immensely to watch and read their stories. James Altucher writes a great blog about personal development and shares his own ups and downs in his career. Nick Vujicic was born without arms and legs. That’s right, no arms or legs. He was bullied so badly that he contemplated suicide. He’s now a hugely successful motivational speaker. Watch his Ted Talk:
  • Embrace uncertainty. This comes from Deepak Chopra’s “Seven Spiritual Laws of Success” which I’d recommend reading and rereading. It’s really only part of Deepak’s message, but one that ties very deeply to encountering difficulties. Acting from a place of fear or depression won’t do anything to help you overcome your situation.
  • See the abundance. When times are hard, you see what’s missing and what you don’t have. The world feels scarce, because you’re focused on the scarcity. But there’s another side to it. Think of what’s abundant in the world. Make a list. You don’t have a job, but that can change very quickly. The U.S. economy is adding 200,000 new jobs a month! Why can’t one be yours?
  • Become grateful. Practice gratitude. Read “The Magic.” You’ll start to see that how even at what may seem like the lowest point in your, you have countless things to be grateful for. When you see that and recognize that everything will change.

What is the hardest thing you have ever done?

photo-1456406644174-8ddd4cd52a06Originally posted on Quora, answering the question: What is the hardest thing you have ever done. Follow me on Quora.


Start a business with $100. Without any partners. And grow it to millions of dollars in annual revenue.


I started my business, Mediakix, in 2011 when I was 36 years old. I hadn’t had experience running a business before and had had very limited management experience. In truth, having worked primarily in sales, I hadn’t actually even managed a single employee before.

95% of companies never make it to $1M in annual revenue. Most companies fold within four years. We hit $1M in annual revenue in our third year, and continue to grow strongly in a hyper competitive field with almost all of our competitors have raised millions of dollars. And I’ve done it all without any start up capital. In fact my credit was so bad when I started, I didn’t even have credit cards to fall back on.

Most start ups have 3-4 founding partners minimum. In rare instances, do they have 2. Most people advise against ever trying to start a business with just 1. There may be a handful of instances that venture capital funds have ever invested in a company with a sole founder because they believe the inherent odds of success are so low. I was too busy to pay attention to these odds. I couldn’t list all the challenges I’ve encountered starting and running a business as the only founding partner; the list would simply be too long.

Starting a business is like jumping into the gladiator pit. You don’t get a break, a chance to stop, rest or recover. All of your skills are tested every day, and you’re made glaringly aware of your deficiencies. If you’re in a field worth starting a business in, you’re in a constant battle against your competitors. The greater the potential for success in the field, the more competitors you’ll have.

I had to learn leadership, management, business strategy, finance, product development, sales, marketing, human resources and everything else under the sun of business. Knowing I couldn’t be good at everything, I knew I still had to be at least knowledgeable about everything. When I wasn’t working, I was reading and taking online courses of all the former topics. It never seemed enough; and in spite of the business’ success, still doesn’t.

I couldn’t complain because I had no one to complain to. When you’re an entrepreneur, no one (except other entrepreneurs) understands your challenges. You don’t get a break, you’re terrified to take a vacation, and you have to make payroll every two weeks. The more you grow, the more you have people depending on you to make the right strategic decisions and to continue to grow.

Add to that the fact that I had zero start up capital and never took a loan or investment. All of our growth was funded on cash flow. It was a constant battle of fighting to win new business to add more employees to win more business. There’s an extraordinarily thin line between growth at the exact right rate, not growing fast enough to keep up with the market or our competitors, and growing too fast for our available cash.

Running and growing the business was so stressful, I developed near constant anxiety. I had two severe bouts of back pain that left me bed ridden for days, and I put on 20 lbs. I’m now proud to say that I’ve curbed the anxiety through daily meditation, and have returned to exercise and stretching to improve my health and weight; but, in short, it’s safe to say entrepreneurship is not good for your health.

I’ve learn so many incredible lessons. It’s trial by fire. I was, in part, by driven by the adrenaline of running my own business and, in part, by the absolute fear of failing. Failure isn’t the least bit sexy when you’re running your own business with your own money and not investor’s. Failure is just that, failure; and it’s not an option.

It was never easy. Nothing about a start up is. To quote Jason Calacanis, I chewed rocks and spit glass. I’ve lost my biggest customers, I’ve had my best employee leave at a critical juncture, I’ve made too many mistakes to count, and I’ve nearly run out of cash on a dozen occasions. But like all the hardest things in life, when you come through, you experience the greatest rewards. The business’ success has given me the most incredible feelings of accomplishment, pride and gratitude.