Quit your day job smartly & safely (review of How I Built This by Guy Raz)

Dreaming of being your own boss?

Don’t quit your day job. At least not yet. Keep putting in your 40-hour work week and spend your free time being entrepreneurial.

That steady paycheque will buy you a longer runway for getting your business off the ground.

“Most of the successful entrepreneurs I’ve met left the comfort of their previous lives as safely and smartly as possible,” says Guy Raz, who’s interviewed hundreds of entrepreneurs as an award-winning journalist and author of How I Built This.  Very few entrepreneurs made blind leaps without safety nets.

Daymond John continued to wait tables at Red Lobster for six years after launching his hip hop apparel company FUBU. John used a month’s worth of wages and tips to buy a classified ad in the New York Times. That ad secured funding at a pivotal moment for his fledgling company. Nike co-founder Phil Knight kept working for five years as a certified public accountant while Southwest Airlines co-founder Herb Kelleher ran his law practice for 14 years. 

“Having a fallback plan does not mean you are building an escape hatch from your dream,” says Raz.“It’s not an excuse not to try hard, nor is it a ready-made reason to quit. It just means you’re given yourself a cushion at the bottom of your entrepreneurial leap of faith so that if you do crash, you can bounce back to fight another day.”

Raz shares key insights, lessons learned and inspirational origin stories from entrepreneurs who’ve launched companies that include Five Guys, Away luggage, the Headspace meditation app, Slack, Method, AirBNB, the Boston Beer Company, 5-hour Energy Shots, Shopify, Dropbox, TRX, Clif Bar, Dippin’ Dots, Rent the Runway and Netflix.

“It’s never been easier to make this journey,” says Raz. “So many entrepreneurs have done what you are about to do. You have a chance to prepare for what’s coming your way – if you are willing to learn from these unwitting helpers. They’ve made every mistake. They’ve fallen into every trap. They’ve taken every wrong turn. And the good ones – the successful ones – only made those mistakes, fell into those traps, took those wrong turns…once. Because they borrowed from the entrepreneurs who came before them as well. They heard the stories and learned the lessons. Now it’s your turn.”

Raz made the entrepreneurial journey himself as a radio host and podcaster. And like all entrepreneurs, he’s wrestled with crippling despair, doubt and anxiety. There will come a point when you’re ready to quit. You’ll feel completely alone and believe your world is collapsing.

This is when you put down Raz’s guidebook and crack open a notebook. “Starting a business is difficult. It is a twisting road with hours, days, weeks and months filled with struggle and failure and self-doubt and even tears,” says Raz.

“When that happens, I want you to pull out a notebook and write those worries down. I want you to trap them on the page, so that you can look at them the next day, the next week, the next month, the next year and realize that while every challenge and crisis you face in the pursuit of your idea feels like it could be the end of it all, it’s not, I promise.”

Launching a business during a pandemic is scary. But putting your entrepreneurial dream on indefinite hold and staying in a soul-crushing job that makes you miserable and fills you with regret is far more dangerous. Start your journey by reading Raz’s book, putting a notebook on your nightstand and sticking with your day job for a little while longer.

This review first ran in the Oct. 30 edition of The Hamilton Spectator.

Jay Robb serves as communications manager with McMaster University’s Faculty of Science, lives in Hamilton and has reviewed more than 500 business books for the Hamilton Spectator since 1999.

Media relations 101 for entrepreneurs

My colleague Jane Allison and I got to spend a morning with entrepreneurs participating in the 2018 Lion’s Lair competition organized by the Innovation Factory in Hamilton, Ontario.

We offered up media relations advice to an amazing group of job creators, prosperity builders, problem solvers and change makers.

Jane and I have been running free media relations workshops since 2007 as a way to thank non-profits, community groups and entrepreneurs who have inspiring stories to share.


Review: Perennial Seller – The Art of Making and Marketing Work That Lasts

sellerThis review first ran in the Aug. 28 edition of The Hamilton Spectator.

Perennial Seller: The Art of Making and Marketing Work That Lasts

By Ryan Holiday

Portfolio / Penguin


I’ve got a lot of time for anyone who sacrifices a steady paycheque and a pension to build a business and create jobs.

So I was happy to spend a morning last month talking media relations with entrepreneurs who were vying for the final top 10 spots in this year’s Lion’s Lair competition.

We covered a couple caveats before getting into how to pitch stories and talk with reporters.

Media coverage is a good thing. But there are just 24 hours in a day. Time spent talking with reporters could be time spent meeting one-on-one and face-to-face with prospective investors and customers. That’s job one for aspiring entrepreneurs.

The second caveat: good media coverage won’t save a bad product that’s all hat and no cattle.

Media strategist Ryan Holiday would agree. Whether you’re building a new product, launching a new service or writing the next great Canadian novel, invest the majority of your time creating something great before promoting it.

“Crappy products don’t survive,” says the author of Perennial Seller. “Promotion is not how things are made great – only how they’re heard about.”

We’ll hear rave reviews about your product if you’ve nailed the answers to two questions.

Who’s your product for?

And what do they get for their money?

“If you don’t know – if the answer isn’t overwhelming – then keep thinking,” says Holiday. “It’s not that hard to make something we want, or something we think is cool or impressive. It’s much harder to create something other people not only want, but need.”

We’ll ignore your product if it’s merely a marginal improvement over whatever we’re already using.

To get our attention and our money, create something that’s bold, brash and brave. The alternative, says Holiday, is to try selling us something that’s derivative, imitative, banal and trivial. This leaves you with a boring product that’s liable to get crushed by relentless competition.

Using outside feedback to test, tweak, polish and perfect your product is also one of the keys to creating a perennial seller that stands the test of time. “Nobody creates flawless first drafts. And nobody creates better second drafts without the intervention or someone else. Nobody.”

When you’re ready to promote your product, don’t outsource the job and walk away. No agency or consultant will care as much as you, says Holiday.

You need to apply the same amount of creativity and energy into marketing that you put into making your product.

“We have to take this thing that means so much to us and make sure that is primed to mean something to other people too for generations to come. And the best person in the world to accomplish this difficult task? You.”

The harsh reality is that none of us actually care what you’ve made. We don’t care because we have no idea what it is. We didn’t dedicate years of our life to creating it. And even when we know what you’ve done thanks to your marketing efforts, we’re going to care far less than you’d like.

“Accepting your own insignificance might not seem like an inspiring mantra to kick off a marketing campaign but it makes a big difference,” says Holiday. “Humility is clearer-eyed than ego – and that’s important because humility always works harder than ego.”

Holiday’s worked hard to offer up clear-eyed advice to anyone who’s dreaming about creating something truly great. Success isn’t guaranteed but Holiday will put the odds more in your favour.

@jayrobb serves as director of communications for Mohawk College, lives in Hamilton and has reviewed business books for the Hamilton Spectator since 1999.

Review: Smart People Should Build Things by Andrew Yang

smart peopleThis review first ran in the April 28 edition of The Hamilton Spectator.

Smart People Should Build Things: How to Restore Our Culture of Achievement, Build a Path for Entrepreneurs and Create New Jobs in America

By Andrew Yang

Harper Business


Kudos to you on graduating top of your class.

So what’s your next move?

Off to law school? Business school? Medical school?

How about choosing none of the above and opting instead for a Steeltown start-up?

Your parents may not approve but author Andrew Yang would congratulate you on a smart career move. And the rest of us here in Hamilton might just throw you a parade.

Yang is founder and CEO of Venture for America (there’s also a Venture for Canada for top grads north of the border). He’s out to create an army of company builders with a sense of purpose.  His non-profit enlists freshly minted grads south of the border to join start-ups and help revitalize cities and communities through entrepreneurship.

Right now, the best and brightest aren’t flocking to start-ups. They’re taking the lucrative and well-traveled path to work as bankers, lawyers, consultants and doctors in a handful of major cities.

“Achievers want to achieve and that’s what achievement now looks like,” laments Yang. “These structured paths are clearly laid out, and are pursued collectively by many – or most – of the students who have been screened and sorted as the academic and cognitive elite. These prestige pathways have become the default options.”

We’re witnessing a hyper-allocation of top talent flooding professional service industries. While it’s easy to see the upside, Yang cautions there’s a downside that too many grads ignore.

“If you work in professional services, you will be paid handsomely and have a brand-name firm on your resume. You’ll gain skills, confidence and exposure.

“But you may also become heavily socialized and specialized, more risk averse and accustomed to operating in resource-rich environments with a narrow set of deliverables. You’ll be likely to adopt an arm’s length relationship with your work. You won’t build anything; instead, you will compartmentalize and put the armor on each day as deals, clients and colleagues come and go.”

And should you find yourself bored, burned out or out of a job, Yang says it’s often toughen than anticipated to change careers.

At a start-up, you’re working on something you own, believe in and care about. “You’ll be 100 per cent engaged and motivated. You can lead an integrated life, as opposed to a compartmentalized one in which you play a role in an office and then try to forget about it when you get home. You can define an organization, not the other way around.”

The work will be gritty and unglamorous. Yet you’ll learn how to get things done. You’ll be comfortable making decisions working off limited knowledge. You’ll create and improve products.  You’ll know how to win and keep customers. And you’ll discover what it takes to hire, manage and lead a team.

All of that experience is great for a long and successful career. And it’s great for our community, given that start-ups and growing companies create the bulk of all new jobs.  “If you want to spur long-term job growth, you want as much talent as possible heading to new firms so that more of those firms can succeed, expand and hire even more people,” says Yang. “Having the right people early on can make the difference.”

Yang says it’s unrealistic to expect freshly minted grads to go forth and successfully launch companies on their own. “Building things is very, very hard. The best way to become an entrepreneur is to learn from a more experienced leader as he or she builds a company.”

Along with creating those hands-on learning opportunities, Venture for America provides training, networks and support for top grads who are working with start-ups in cities like Detroit, New Orleans and Cleveland.

So if you’re headed to a spring convocation cermeony, skip the obligatory copy of Oh, the Places You’ll Go! and give this book instead to your freshly minted grad. And be sure to highlight one of Yang’s favourite quotes from an unknown source on page 68.

“Entrepreneurship is living a few years of your life like most people won’t, so that you can spend the rest of life like most people can’t.”

Review: Startup Communities by Brad Feld

Startup CommunitiesThis review first ran in the Jan. 14 edition of The Hamilton Spectator.

Startup Communities: Building an Entrepreneurial Ecosystem in Your City

By Brad Feld


A question from the audience left Brad Feld stumped.

Feld, an early stage investor, entrepreneur and author of Startup Communities, was talking about Boulder’s thriving startup community with a local business and government crowd.

“What do you think ecodevos should be doing to help?” someone asked.

Feld was stumped. He had no clue what ecodevos were. “All I could think of was ‘Whip It’ from the punk rock band Devo and I had to restrain myself from blurting out ‘whip it, whip it good,’” says Feld.

He soon realized he was being asked about the City of Boulder’s economic development department. His advice?

“First, stop calling yourself an ecodevo since I’m certain there’s not a single entrepreneur in the room who has any idea what that means. “

Feld added that the economic development folks should stick to their role of being feeders for Boulder’s startup community and start asking entrepreneurs what they need to succeed.

“Once you’ve asked, you have a choice. You can say ‘we aren’t able to do that’ or ‘excellent idea — we are going to do that now.’ The worst thing you can do is to be in the middle with entrepreneurs.”

According to Feld, a successful and sustainable startup community needs both leaders and feeders such as economic development departments. Both are important, yet they have different roles and there can only be one true leader.

Regardless of the city, Feld says it’s essential that entrepreneurs who’ve co-founded high-growth companies actively lead the startup community. “Lots of different people are involved in the startup community and many non-entrepreneurs play key roles. Unless the entrepreneurs lead, the startup community will not be sustainable over time.”

Not only must entrepreneurs lead with a “give before you get” philosophy, they also need to make a long-term commitment to their community. “I like to say this has to be at least 20 years from today to reinforce the sense that this has to be meaningful in length.”

Established entrepreneurs also play a key role in fostering a philosophy of inclusiveness. Anyone who wants to get involved should be welcomed and quickly plugged in. “Building a startup community is not a zero-sum game in which there are winners and losers: if everyone engages, they and the entire community can all be winners.”

Feld says there shouldn’t be a leader of the leaders and the classic patriarch problem is one to watch out for (“old white guys who made their money many years ago but still run the show”). The best startup communities aren’t hierarchies. They’re loosely organized networks with new leaders constantly stepping up, taking on and doling out community building assignments.

“Becoming a leader in a startup community is a function of what you do rather than being voted into office or selected by some secret committee in a dark, smoke-filled room,” says Feld.

When talking to groups about startup communities, Feld always asks how many people in the room are entrepreneurs. “If less than half the audience consists of entrepreneurs, there’s a fundamental problem.”

Feeders are everyone else in the startup community, including government, universities, investors, service providers and large companies.

Feld says universities have five resources that are relevant to entrepreneurship: students, professors, research labs, entrepreneurship programs and technology transfer answers. “The first two resources, which are people, are much more important than the last three,” says Feld. “Every year, a new crop of eager freshmen arrive on campus. Regardless of what they end up doing, they all bring new ideas and fresh perspectives to the community.”

The core entrepreneurship activity at the University of Colorado Boulder happens in the law school. Along with hosting conferences and groups, the school offers an entrepreneurship law clinic.

The two most important contributions that large companies can make are providing convening space and resources for local startups and encouraging startups to build companies that enhance the large company’s ecosystem.

Feld also says successful startup communities need regular activities like hackathons and startup weekends that bring and bond leaders and feeders together in working on real entrepreneurial activity.

“My favourite thing about startups is that they don’t require anyone’s permission,” says Feld, who in his book shows how a city with about a fifth of Hamilton’s population became a startup powerhouse. “Great entrepreneurs just start doing things. These are same entrepreneurs who can be the leaders of their startup community. They just do things.”

This is a must read and a powerful call to action for Greater Hamilton entrepreneurs.