The Start-Up of You

The Start-Up of You by Reid Hoffman and Ben Casnocha
(buying through that link supports Expat Chronicles)

“Being an entrepreneur isn’t really about starting a business.  It’s a way of looking at the world: seeing opportunity where others see obstacles, taking risks when others take refuge. Entrepreneurship has always driven innovation in the private sector, but increasingly it’s essential to progress in government and the nonprofit sector, too.  Whatever career you’re in – or want to be in – The Start-Up of You holds lessons for success.” – Michael Bloomberg

I’m beyond burned out on career advice, but this book was different because (A) it’s for 21st century market conditions written by 21st century entrepreneurs and (B) Ben Casnocha is a friend. I was already hip to many themes since going independent, but having my approach validated by two Silicon Valley heavyweights reinforces by resolve. And it did give me new ideas. Here I’ll touch on the book’s important points.

For the last sixty years, the job market for educated workers worked like an escalator. After graduating from college, you landed an entry-level job at the bottom of the escalator at an IBM or a GE or a Goldman Sachs. There you were groomed and mentored, receiving training and professional development from your employer. As you gained experience, you were whisked up the organizational hierarchy, clearing room for the ambitious young graduates who followed to fill the same entry-level positions. So long as you played nice and well, you moved steadily up the escalator, and each step brought with it more power, income, and job security. Eventually, around age sixty-five, you stepped off the escalator, allowing those middle-ranked employees to fill the same senior positions you just vacated. You, meanwhile, coasted into a comfortable retirement financed by a company pension and government-funded Social Security.

That is OVER. This book explains how to survive now that that era is OVER. Why is that era over? Globalization and technology. Technology “automates jobs that used to require hard-earned knowledge and skills, including well-paid, white-collar jobs such as stockbrokers, paralegals, and radiologists … If technology doesn’t eliminate or change the skills you need in many industries, it at least enables more people from around the world to compete for your job by allowing companies to offshore work more easily – knocking down your salary in the process.” So the job market has changed, and so should your approach.

There used to be a long-term pact between employee and employer that guaranteed lifetime employment in exchange for lifelong loyalty; this pact has been replaced by a performance-based, short-term contract that’s perpetually up for renewal by both sides …

Job security is largely a thing of the past. So many industries have been overhauled by technology or globalization, the only safe careers are highly specialized, local trades (nurses, police officers, welders, etc.).

Andy Hargadon, head of the entrepreneurship center at the University of California-Davis, says that for many people “twenty years of experience” is really one year of experience repeated twenty times.

Given this new era, if you’re in career cruise control you’re actually taking the most dangerous risk. Because one of the two forces – technology or globalization – will come knocking some day. And when that day has come, how much will your twenty years of doing the same, obsolete job help? Start preparing yourself for industry overhaul now.

Plan Z

Develop a Plan A, Plan B, and Plan Z. Plan A is your dream. Plan B is what you shift to if the dream becomes unattainable or unrealistic. Plan Z is your ultimate fall-back plan. Plan Z allows you to take the risk on Plan A and Plan B. It’s the absolute worst-case scenario you must do to survive. My Plan Z is returning to St. Louis to bartend.


The book talks a lot about risk and how entrepreneurs manage risk – intelligent risk. Remember, if you’re in cruise control you’re taking the most dangerous risk of all – unintelligent risk.


The book talks a lot about serendipity – ‘a “happy accident” or “pleasant surprise”; specifically, the accident of finding something good or useful while not specifically searching for it.’ Included are best practices in maximizing probability of incurring serendipity.

I published my notes of the actionable recommendations on Slideshare. Here are the most relevant:

Review how you spent your last six Saturdays. How you spend your free time may reveal true interests and aspirations.

This advice is nothing new, but it will always hold true: Do what you love and the money will come. Do you like what you do? If not, start the transition into something you enjoy. Something you do on your days off.

If you stopped going to the office, what would NOT get done? What’s a day in the life of your company without you there? That’s where you add value, your strengths.

This is ultimately why I left the corporate world. Especially at huge companies, if I didn’t show up for a week, the company’s bottom line wouldn’t look any different whatsoever. Receiving a safe and secure paycheck wasn’t satisfying. Since little would’ve changed if I never showed up at my big corporate, entry-level gigs, nothing indicated where I was adding value. My strengths – whatever they are – weren’t being used. Maybe you’re happier with security than intellectual fulfillment, but those kinds of jobs are the ones most likely to be downsized. I wasn’t happy being a peon, so I went out on my own.

Establish an identity independent of your employer, city, industry. Reserve a personal domain ( Print business cards with just your name and personal email.

This is something EVERYBODY should do in the 21st century. If you don’t have a blog, you’re in the 20th century. For Christ’s sake you can get a FREE site hosted at Hosting a site on your own domain could be as cheap as $13 / year.

No matter what your profession, you need a blog or personal website. It’s such little effort to have a digital home for any potential employer or customer to read about you. Whatever you’re passionate about – teaching English, journalism, the beer industry, politics, whatever – blog your ideas about those topics. Articulating your passion online could potentially set you aside from the competition when applying for a job, client, grad school, whatever. It’s an online sample that demonstrates how you think. I think resumes, CVs, and hojas de vida will be less and less relevant as time goes on. Your web presence will be more important.

You don’t have to write about snorting coke, getting in fights, or banging whores. And you don’t have to write something every week, or even every month. It can be sterile and infrequent. But you have to write something. You have to demonstrate that you have a brain. You have to demonstrate that you’re not an apathetic sheep willing to go along wherever the tide takes you.

Identify 5 people you spent the most time with in the last 6 months. Are you happy with the influence those 5 people are having on you?

This is one that I’d been struggling with in Bogota. Unfortunately, two of those five people would be The Mick and one of the deported guys. I like hanging out with them. Unfortunately, you become like those you surround yourself with. I may have not realized it, but they were having an effect on me. To achieve my goals and dreams, I need to hang around other people with the same priorities. The problem is the trouble is more fun.

Introduce two people who don’t know each other. Then think of a challenge you’re dealing with and ask an existing connection for an introduction to someone who could help.

This was something I started to embrace as my blog became more popular in Bogota. I enjoyed introducing people who could help each other, even if I didn’t receive any kind of compensation. It’s like social karma. Help others and it’ll come back.

Imagine you got laid off today. Which 10 people would you email for advice? Reach out now.

Reach out now, but also think how technology or globalization will change your industry. Specifically smartphones and increasing digital capacity, or an increasingly educated workforce that can perform white collar labor from abroad.

Create an “interesting people fund” for coffees, lunches, and travel costs to meet new people and shore up existing relationships.

This is part of the serendipity strategy. Leverage your network to create opportunities. There’s a sales book out there titled, Never Eat Alone. I haven’t read it but I love the title. Always be meeting people, always connecting.

Budget time for randomness. Read a book you wouldn’t otherwise read, take a coworker from a different department to lunch, attend a speech or seminar in different field.

Maximize serendipity.

Find an industry event or ideas conference to attend in the next six months.

This is something I’d largely neglected in Bogota. Once at a gringo event, I had a few people turn noses up at me because they knew who I was. They knew about this blog. After that night I decided I didn’t give a shit about the square gringos in Bogota. They can turn their noses up all they want in their boring northern bubble.

That’s the wrong idea. Proactive networking and maximizing serendipity is crucial. I need to swallow my pride and get back out there.

Set aside a “yes day” – say yes all day and note the serendipity that results.

Interesting idea. No matter what request comes your way, you must accept and see what happens. Maximizing serendipity.

Identify those in your network who always find interesting opportunities. Try to understand why they’re hubs of opportunity and resolve to meet more people like them.

To be honest, I’ve actually been this person because of my blog. I’ve had opportunities to market stem-cell products, financial services, legal services, porn, webcam girls, insurance, cell phones, and more. It’s a good problem to have when you must pick and choose the industries to work in. This goes back to the power of having a BLOG, and demonstrating an ACTIVE MIND on that blog.

Start your own group of association. Regular luncheon, one-time meetup – what’s important is you convene friends and exchange ideas. Create a simple wiki or LinkedIn group to organize and share details.

I’m in the brainstorming phase of having expat get-togethers in Bogota for like-minded people – the kind of people who enjoy this blog.

Identify and take on risks that are acceptable to you but others avoid. Are you okay having less money in savings with a low-paying but high-learning job? Or maybe a month-to-month contract as opposed to something long-term? Find a project with these kinds of risks.

This is about taking intelligent risk. If you have a wife and kids, you’re options are limited. If you don’t, you should be more aggressive in taking risk those guys can’t. Exploit risks that others aren’t willing to take. Make it a competitive advantage.

Plan to increase the short-term volatility in your life. How can you take on new projects (or jobs) that involve more ups and downs – more uncertainty?

This is something that doesn’t apply to me. My life has been volatile since I was born. The longest I’ve lived at one address was four years from 10 – 13. I haven’t lived in one place for over a year since 2006-2007.

Schedule 3 lunches in the next few weeks: 1 with someone higher than you in same industry, 1 with old friend, 1 from adjacent industry. Engaged conversation leads to serendipitous intelligence.

Be aggressive in networking, maximize serendipity.

Become a go-to person for other people in your network. Make your interests and skills known via blogging, email, discussion groups.

Again, the most important takeaway from this book is to create a web presence. If you don’t have one, you’re literally nobody. Put yourself out there. Don’t be a pussy.

The Start-Up of You by Reid Hoffman and Ben Casnocha

Here are all my slides from The Start-Up of You:


One comment

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s