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From Secretary to CEO: One admin assistant turns entrepreneur and scores former boss as first client

January 2, 2009

Emily C. Morgan is a calm lady, not at all the  kind of loud-talking, forceful person who you might assume would go the intrepid route of writing off her company and boss and starting her own business.


Emily’s virtual assistant business, Delegate Solutions, started from her home when she was pregnant AND working full time as an executive assistant to the top management at her former employer, a local mid-sized company.  When the company unveiled plans to move to a new location several towns away, Emily faced an extended commute (as a big pregnant lady!), and her enthusiasm for being somebody else’ perpetual gopher, unsurprisingly, started to wane.

Emily decided that what she really wanted was to work from home, and have  more of a hand in her own employment. Working as a virtual assistant started as a side business for Emily, something she was doing to fill in those other 30 hours after she put in her regular 40 (yep, that’s right, this mama works about 70 hours a week).

Like Chad Hartvigson, Emily was shrewd, confident and probably a smart enough strategizer to beat last year’s Russian chess master. That’s why Emily’s first high-powered clients were her former bosses. Not only did this young mom-to-be, and sole breadwinner for her family,  negotiate a work-from-home deal, she actually convinced them that her QUITTING would be a good thing, and that they should continue to give her money as clients of her business.

So sly it’s damned foxy.

During our chat a few weeks ago, I discovered that you CAN be a nice young lady like Emily, ‘cheat’ on your company by starting your own, win them back, and, with a healthy dose of hard work, get just exactly what you want.

What I learned from Emily

1. Ask and receive. After starting her business, Emily had a dream to be on the Martha Stewart Living show. She wanted it, and decided she would get it. No matter that Martha’s all about cooking and crafting and Emily is an entrepreneur in the cutting-edge, but not very crafty, virtual assistant industry.

After much unsuccessful LinkedIn-mining (which requires its own form of constant asking), she finally got a hookup with a producer for the show, only to be told that Emily’s virtual assistant business was a cool story, but not quite ‘crafty’ enough for Martha. Instead of giving up (as I probably would), Emily kept asking. She eventually asked so many different people, so many times, that she found someone who worked for Martha’s radio show who was agreed to hear her out. A week later, Emily was up in NYC and talking up Delegate Solutions on MSL Radio.

2. All hail the day job! The more entrepreneur types I talk to, the more this one is becoming a major theme. Emily started out small by taking on just a few clients while she continued busting her butt at her regular job. As a pregnant lady, and later as a new mom who was a sole provider, she couldn’t afford the risk of free fall, and she needed the health insurance. Yes, she worked longer hours in the beginning, but to her, this was an investment not so different than putting money toward grad school, or working an unpaid internship.

3. Spin a loss (your company’s’) into a gain (yours AND your company’s’). When Emily first told the three executives at her company whom she assisted that she was going to quit, and to start her own business no less, they were skeptical. However, they were also needy, maybe even desperate, because Emily was a great assistant and had become an important enabler of their own success. Emily worked the ultimate magic when she actually convinced them that they should be happy to let her go, and that they should next enlist the services of her new company, Delegate Solutions, to fill the role.

Did she strong-arm them? Go in to the exec office with hardball negotiations lines written on the palm of her hand? No and no. She simply spoke their language, the much-loved language of money. Emily knew that cost was a concern to them, so she talked up the changeover in terms of cost – the company could save headcount money by purchasing her service instead of maintaining her as an employee. She didn’t bother them with too many details about her personal life as a mother and goals to own her own business. Honestly, nobody but your mom cares about these things, so it’s best to keep them out of important negotiations and explanations. When negotiating with employers – whether it’s for something complex like transitioning them from employer to client status, or for something simple like a raise – stick to the universal language of money and value.

4. Make it All-or-Nothing. In Dan Ariely’s book Predictably Irrational, he describes one study that illustrates how having more options (or even just perceiving that there are more options) can actually distract us from our primary goal and undermine our success. An All-or-Nothing situation actually increases our success – even after factoring in the risk of failure. Emily was her family’s primary breadwinner; her husband had been laid off a few months before and babies are still not allowed to perform wage labor in the state of New Jersey (why, I have no idea…).

Once Emily had enough clients and decided that Delegate Solutions was going to be her main work, she was basically putting her family’s survival on the line. Stupid move? Nope, it was an awesome move. After she saw that her business had a decent chance at succeeding, she set up the ultimate motivating mechanism for herself and made sure that she’d work her butt off. She eliminated failure as an option.

See the full interview notes below.

Why did you think you could start this business by yourself ? Why didn’t you think about joining an established virtual assistant firm?

I never really thought of that as an option. If you’re looking to do admin work and have no headaches, being a subcontractor through some virtual assistant firm is definitely the way to go. But, if you’re looking at this as a big picture, then this is the way to go. The only way to make serious profit is to start your own business. Anything else would only be capping your income potential.

In my case, there was no reason I couldn’t do it for myself, aside from a little fear of not making enough income to support my family. I had a good, realistic business model, and knew it was a way that would allow me to work remotely using the skills I’d perfected through my ten years in admin work.

The key is that you can’t just wake up one day and say “I’m going to do this.” Building a business is a slow process, and I built mine while I was working for somebody else’. It actually helped me because as I was working, I was building up my client portfolio until I could be independent.

How did you learn, or was this just like working for your company (without the commute)?

I didn’t have any business training, I didn’t know what LLC meant, and I didn’t know I had to go through as many hoops as I did, so starting this business took a long time.

I relied on my state’s small business association – a government program – that provided me with a ton of resources to get going with the basics of starting a business.

I also belong to two industry organizations, the IVAA and the DWAA. The virtual assistant industry is very supportive, and I used it extensively to network and find a group to support me.

What does your income look like now compared to being a regular full-time employee?

It’s not totally the same since I have to pay for health insurance, I no longer have a cushy 401k, and I have to pay for my own electronics and software. But, I’m really just starting out, and, with owning my own business, the opportunities ahead are so much bigger than anything I could achieve by working my way up the company ladder.

What does your husband think of all this?

He loves it. I work all the time, but he’s very into being Mr. Mom. When he lost his job, I went full force with the business. He helps me with business things, errands, cleaning, cooking.

I can have a baby, I can bring in some extra money – I didn’t really think anything other than this is a great arrangement.

Now that we’re in the situation that we’re in, this just sort of took off, and I’m just going with it!

It wasn’t what I had planned, but I’m not disappointed. We’re both in our element. I hope that one day I don’t have to work as much as I’m working now, but I’m working on setting up those boundaries. It can be hard when you have a home office because it’s always easy to get to work.

How did you get that fantastic mention in the New York Times?

Writer of nytimes article is a good friend of one of Emily’s clients. BC of the Times piece, she was able to get on Martha, and then NBC, etc.

I really wanted to be on Martha Stewart show. How are you gonna get on Martha Steward?? I worked the netowkr (linkedin) and connected with a producer on linked in.

Then, one day I came across a radio host who worked for Martha Stewart and she put me on her show!

To the producer on the show: found out she was a penn grad, kept emailing her, she finally wrote me back, and said, “I totally want to work for you and I have a  baby!” but this isn’t gonna fit on the show. But, after the Times piece, but I got a client from there and his coach posted to Martha’s blog, and E found out that she was the career coach on Martha Stewart radio. Contacted her…

Tpo be on nbc news – I emailed all the news channels with my story, and somebody called me back! My mba person pitched me to the magazines. “turning your former employer into your client”

Would you recommend this to my CEO’s executive assistant, Melissa?

Having your own company is the most fulfilling and draining things you could possibly do. A lot of people aren’t up for the whole working 70+ hrs per week thing. They don’t have the stomach for it and that’s fine – there are plenty of corporate jobs to be had.

BUT… anyone can do it if they really want it and can envision their own success. I’m not talking about new-agey visualizations, I mean being able to know that you can succeed at something.

My clients (and former employers) love it because they get treated like they’re a customer paying for a service rather than a company having to manage an employee. For me, I’m still an assistant helping them with the same admin tasks as when I was their employee, but it feels completely different to direct your work as part of your own business.

Make Millions Selling T-Shirts to High School Athletes? You Bet.

December 19, 2008

When a friend first recommend that I talk to Chad Hartvigson for this blog, I was skeptical.

A guy who runs a business selling screenprinted t-shirts for high school sports? Not sexy enough. For someone like me who mingles in the self-absorbed, “[NOUN] 2.0” buzz of Silicon Valley all day, every day, the idea of debuting with a t-shirt printer was so unglam as to be a downright blogkiller.

I love being wrong.

A sweatshirt so cute that I might not be so embarrassed about RHS anymore...
A sweatshirt so cute that I might not be so embarrassed about RHS anymore…

Chad’s company, Prep Sports Wear, blows many of the Web 2.0 startups down in SoMa completely out of the water. For one thing, Prep Sports Wear actually makes money (ouch!).

For another, you don’t have to be a fancypants Bay Area yupster to understand the basic American appeal of comfy loungewear with your school’s logo on it. And lastly, though I haven’t yet met Chad in person, he’s got a damn sexy phone persona for a former semipro-baseballer (wink).

During our hour-long conversation last Tuesday night, Chad struck me, incredibly, as being simultaneously innocent and shrewd as hell. He was also pretty fun to talk to, and offered a few surprising nuggets worth repeating.

What I learned from Chad

1. Entrepreneurship does not necessitate expertise. Chad wasn’t a t-shirt manufacturer. He wasn’t a tech guy. He was an athlete who wore t-shirts and was interested in technology. He wasn’t an expert in any of the areas that were core to his business. But, he thought he had a good idea, so his job was to rally the experts.

2. The day job will save you. Prep Sportswear started as a teeny, tiny side project when Chad was still a college athlete. It stayed as a slightly less tiny side project when Chad was a grown-up working at a financially stable, regular job. The security of his day job actually gave him the confidence to pursue his side project to its current glorious state – precisely because everything was NOT on the line.

3. If you don’t like your boss, it might not be your boss’ fault (gasp!). Maybe you just don’t like working for other people, like Chad. Great entrepreneurs recognize this in themselves and, instead of fuming against their company or their managers, channel it into projects that will get them out of the employee lifestyle.

4. Laugh in people’s face. I loved when I asked Chad how he felt when people told him this was a stupid idea, or that he was crazy, or that he would fail. Instead of just giving me some inspirational blahblah about adversity making you stronger, or even just saying he felt bad, the way I probably would have felt, he just said he laughed. People don’t know what they don’t know, and it’s funny sometimes. But seriously, don’t take it (or them) too seriously.

See the full interview notes below.

How did you get your start?

I was in college at the UW, playing baseball for the team there. Huskies football gear was everywhere, but you could never find a sweatshirt about anything besides football. We wanted something for us, so, as team captain, I started taking orders.

The first year we sold to players and families. The next year, the coach asked me to do it again, and to help out with the softball shirts the year after that. It came from a need by the team, it wasn’t a business idea, so I always sold at a cost.

I had this idea that we could really make a business this way, selling one-off, customized t-shirts in low volume to a massive customer base. But it was 1995 and the Internet was just starting to take off. There was no real e-commerce then and no way to make it happen with the technologies that were available.

So, then by some magic you still made it into a multimillion dollar biz?

Well, eight years later, my dad, who sold t-shirts from manufacturers to retailers, got laid off and needed some help. My brother and I thought about ways we could bring him into our insurance sales business at the time, but there was really nothing he could do there. So, we started thinking, Hey, what about the t-shirt idea…

So my dad and I ran a beta test with six schools in the area. We went around and did a bunch of surveys with them, and figured out that the concept worked. People liked the idea and thought an online store for school merchandise would be very useful.

Oooh… beta test. How did you figure out which six schools to survey? Some complex algorithm, I assume?

Those were the only six schools that actually returned our calls.

Customized merchandise for high schools – doesn’t that go against most desirable business principles (high volume, low-cost mass production, deep-pocketed customer)?

Lots of people were out there trying to sell 500 shirts to 1 customer, but I wanted to sell 1 shirt to 5000 customers.

I was looking at the long tail of consumers, and I saw a need. Most printers don’t even have Internet in their offices, and they won’t serve you if you just want to a couple of shirts. I wanted to aggregate that market.

Did you know that you were going to scale your business to its current degree – affiliate program, corporate clients, targeted ads and co-branded stores – from the beginning?

Our goal was to scale the business from day one. Anything other than a “big hit” would not be worth the time or risk.

How did you craft your vision without being an expert in the technology that would take you there?

I don’t think you need to understand the technology. You really need to understand your vision and be able to communicate it to others in a way that allows them to share it. Once you’ve done that, you can attract others to help you execute it.

I had some friends working at big tech companies in the area, so I talked to them a lot. Eventually, one of them introduced me to Ivan, who became my lead developer, and eventually the CTO.

How did you pay Ivan when you first met him?

Uh, well, I paid him entirely on equity.

It helped that he had some pretty good stock options from his InfoSpace days to help him keep a roof over his head.

How long did it take him to decide to work with you?

I met him at a Starbucks on a Wednesday night. I told him about the idea, and I was just really excited about it. He said he’d let me know within two days, and on the second day, I got a call from him.

Wow. When I get ideas, I only feel good about them if other people tell me, “That’s a great idea! You should do it!” Didn’t a lot of people tell you it was a stupid idea in the beginning? And then here you’ve also gotten this nice Russian man involved…

Yes, a lot of people told us it was crazy, or stupid. People laughed, and no one would believe us.

But, as a person who’s played baseball since being a little kid, including professionally, you have a lot of people telling you that you can’t do this or you can’t do that. In sports, people are always trying to talk you down – you can’t succeed unless you figure out that all that doesn’t matter. The only thing that matters is what you believe personally.

The fact that it started as a side project was important too. I had my other business that I worked on with my brother, and I knew I’d be financially ok with that, so it took the pressure off a bit. I also never took VC funding or anything like that. It was just a little bit of money from family and friends, so I never felt like I had to go running around pleasing all these funders and doing things with my company that I didn’t want to do.

Ivan  didn’t really get the t-shirt idea at first, because in Russia you had a choice of either a black t-shirt or a white t-shirt. It didn’t make sense to him why people would want all these customized sports shirts. But, for someone who’d come from Russia only four years prior, he really embraced the idea of American entrepreneurship and was looking to get away from the corporate atmosphere of his last job.

So, why did you do it all? Bucks? Babes? To fulfill your dream to be on Ask The Entrepreneurs?

I grew up watching my dad going through the ups and downs of working for other people. In college, my goal became to never work for someone else. And, I saw an opportunity that wasn’t there in the insurance sales business I worked on with my brother, where your success was always 1:1 – limited to how much you as one person could get done.

Our business is basically a technology company. We’re now 50 people using technology as a platform to monetize a massive base of consumers. We offer schools and teams completely customized items with a minimum purchase of one, and we’re making money doing it.

Why Entrepreneurs?

December 14, 2008

What is an entrepreneur?

An entrepreneur is someone who’s engaged in their lives – their work, their people, their exercise regimen, all of it – and achieving an admirable measure of public success.


They DON’T have to be a billionaire tycoon – in fact, I prefer if they’re not. All too often, people who arrive at that level of financial success are a little too media-friendly. So much so that they trade in candor and fallible authenticity for a persona that will look good in print.

They DO have to be a basically good person who takes fearlessness and positivity where ever they go, even if they stumble into some sort of mineshaft. People make mistakes, and entrepreneurs are serial mistake-makers. The true entrepreneur is like a smarter, more successful version of Wil E. Coyote from Loony Toons – cunning, even sneaky, and able to survive ubiquitous TNT and cliff falls only to walk away to try again.

Why entrepreneurs?

Entrepreneurs have a lot to teach us – we’re corporate drones, we’re the masses of nameless coders, we’re secretaries, house-wives or -husbands, straight-A students who’ve never wandered off the path beaten for us by our parents. We’re artists who still haven’t figured out how to make a living from our craft, or aspiring writers who are too rejection-averse to send around our work.

The main difference between us wistful worker bees and the world’s entrepreneurs? We’re scared. They’re not.

Why read Susan Su?

I’m Susan, I ask a lot of questions, and I don’t know everything. That is precisely why you should read along as I learn from hundreds of people who did something right.


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