Christopher Wink receiving the 2015 Be Your Own Boss Bowl 'Self Made and Making Others' award

Temple University’s Fox School honored me with the ‘Self Made and Making Others’ award

I’m proud to say that the Fox Business School of my alma mater Temple University honored me with their third annual ‘Self-Made and Making Others’ award during the Be Your Own Boss Bowl.

The honor is a recognition for entrepreneurial work that helps others do the same. I gave a keynote address to students and other alumni, which I wrote out and shared below but mostly just used as notes.

PREPARED REMARKS: Find photos on Facebook here.

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One thing you can learn real quick in business reporting is how far the spread of any scale is.

Your first $1 revenue, crossing $500,000, topping $1 million, doing more than $10 million. Your first employee, having a team of five, doubling to 10 and hitting 20 and then 50 and 100 and then 500. A year-old and then five and 10 and 20 years. There are mushier metrics too, like your community impact and reputation among your customers. There, too, there are ranges.

So though I’m very proud to be here receiving the “Self-Made and Making Others Award” from the Temple University Innovation and Entrepreneurship Institute housed at the Fox School of Business, please know that I’m very aware of my place at the far more modest side of that scale.

As shared, my name is Christopher Wink and I’m the cofounder of Technical.ly, a six-year-old local tech news organization with a $1 million 2015 budget, 10 employees and a dozen more who daily help us publish in five East Coast markets — Philadelphia, Brooklyn, Baltimore, DC and Delaware. We are reporters who put out a daily news product on local tech communities but we also take responsibility for moving that community forward. One of the ways we do that is by convening our communities through events — tomorrow is the official kickoff of the fifth annual Philly Tech Week Presented by Comcast, with more than 150 events around tech and entrepreneurship packed throughout the city over the next 10 days. (You should join us tomorrow by City Hall 6-9p for our Arcade at Dilworth Park, with an outdoor beer garden and locally made video games and tons of fun stuff, there’s also a Startup Crawl touring local tech startup offices before it)

I’m a journalist in his late 20s who somehow found himself running a small, low-margin publishing company that’s doing things a bit differently.

If the Be Your Own Boss Bowl is worth its name, many of you should build companies with bigger footprints in short order. I look forward to reporting on your growth.

But thanks to IEI Director Ellen Weber, and others, for now, I’m up here, and for the next 15 minutes or so, you’re stuck with me. As a reporter, I’ve listened to my fair share of speeches, so I’m going to be clear, I’m going to keep it moving and I’m going to leave some time for a few questions from those of you who were kind enough to pay me any attention.

In the next 15 minutes, my goal is to share a few pieces of advice on starting and growing a business. But here’s the reason why it’s worth listening to an idiot kid you’ve never heard of who has a business you’ve never heard of: because I’m way more journalist, than entrepreneur, which means what I share here comes from talking and interviewing hundreds of founders in recent years.

Number One: Don’t be a boss.

With full respect to the name of this competition and the spirit of entrepreneurship and even to Meek Mill, don’t be a boss.

Bosses suck. They haven’t done the work before but they want you to do it better. They don’t care about you as a person. They are authority figures not inspirational ones.

A founder is something different. You’re building a team. You’re testing a model. And to do that, you’re filling all the cracks. From the start you have 100 roles, then as you hire, you have 80 roles and then 50 roles and 20 roles and five roles and then maybe you become a CEO or a CTO or a COO or a board member.

Building an organization from zero means creating definable roles for your new team members. As the founder you absorb and balance and redirect a lot of the in-between stuff. One of the most helpful sentences that any employee of an early-stage company can learn is: “I don’t think that’s what I’m best at and I don’t think it fits in my role, but if it needs to get done for the short-term, I will do it and do it well.”

Growing companies need those kinds of people, and founders have to do that. A boss wouldn’t do the same.

Which brings me to Number Two: Founders aren’t scalable.

Founders are powerful catalysts and transitional figures. They are not longterm stewards of mission. So businesses can’t last being built on a founder filling the cracks but you need a founder to start. CEOs scale businesses. Founders create models. You can be the same person, but the mindset has to change.

Number Three: If you say you’re not good at sales, then you’ve never been desperate enough.

Look, in truth, I’m not great at selling. I’m crummy at negotiating. I second guess myself. I’m inconsistent in my approach. I care more about relationships than getting the details squared away. But I did about a quarter million dollars in sales last year, and it’s a small part of my role.

I remember being in my crappy apartment in Frankford in our first few months of Technical.ly. We had written some stories, attended some events. But we wanted to build a business, one that supported a news organization. And my hand was trembling to make my first sales call. To a bar on Delaware Avenue, for some reason. I failed. And I failed a lot.

And I made about $16,000 that year, including freelancing and landscaping and $150 display ads on Technical.ly Philly. I was terrified. My cofounders were terrified. I was having trouble figuring out my taxes and my student loans. I was drowning.

And so we got better. Fast. Because we had to. Because we were desperate. And scared. I got a side-job and we started figuring out a model. I made $35,000 in 2011 without benefits, working 80 hours a week in relative obscurity. It wasn’t great. But it was better.

I make more now. Not a lot more, but it’s a salary I’m privileged to receive for doing a job I love with people I respect. There are now four of us selling sponsorships and sponsored content and the idea that we’re the best way to get in front of technologists and entrepreneurs in local communities.

Number Four: You Don’t Know Anything.

Because no one does. At some point in growing Technical.ly, I realized that no one knows what the hell they’re doing. Some of us are just better guessers and fakers.

There’s this Baltimore founder who is a source of ours. He had a modest but prominent exit a few years back on a business doing $5 million in revenue, and I was surprised when he told me in confidence that the biggest relief the day the acquisition paperwork was finalized he had was that he knew he didn’t have to worry about making payroll the next cycle.

He was a leader in a tech business community and he had the same basic fear I had: I gotta pay my people. It was a reminder that no one knows anything. You don’t know anything.

But don’t let that keep you down. That’s your strength. We still piss off many in traditional journalism communities because we talk about revenue. We want to report truth to our community but we’re also trying to build a model in which we can sustain a team to do that.

We could do that in part because there was so much we didn’t know. We respect our journalism community’s roots, but we were willing to break when we had to. One of my favorite questions in our newsroom is if that industry tradition is there for a reason or just out of habit. We try to keep the former and ditch the latter.

The balance there is keeping humble in your head, by knowing you don’t know anything, by embracing the fear and uncertainty, by self-deprecating some and knowing that your business can fail, that it almost certainly will fail.

But while humble in your head, be audacious in your heart. Shut your mouth and build a great business. Find a customer, provide extraordinary value and sell them. Repeat.

Number Five: Give a damn.

If you don’t have the energy to care, that’s fine. But this isn’t the right racket for you. It’s exhausting and thrilling and the most rewarding disaster of your life.

You have to want to be great. You have to be so competitive with yourself and your industry. But you also really need to care. That really is the great secret. To care about something.

All the research about what’s the difference between a great teacher and a lousy one, it basically just comes down to whether the teacher cares. Whether someone wants to stay on your team, sure money helps and a fun work environment, but it also matters if you actually care.

You can fake so much in starting a business. You’re gonna fake how serious you are for your first few customers. You’re gonna fake how much you know and how certain you are of the model you’re developing. But you just can’t fake caring.

(Google Doc)

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