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What Does $5K Do for a Small Business?

Our final interview with the APW + Squarespace small business scholarship winner


As November draws to a close, we are officially hitting the time of year at APW when we are talking about money… a lot. There are taxes to be paid and budgets to be sorted out for the next calendar year. So it seemed an appropriate time to sit down and catch up with our APW + Squarespace small business scholarship winner, Tristen Chang of RCG Education, to find out what winning the $5,000 scholarship meant for her and her business.

Of course, the APW + Squarespace small business scholarship wasn’t just about the $5,000. It also came with mentoring sessions from the APW staff, guidance on Tristen’s new website, and we were even able to finagle new headshots courtesy of Sarah Deragon of Portraits to the People. During our mentoring sessions, Tristen and I talked about how she wanted to grow her business, from staffing more tutors, to implementing scheduling software, and figuring out how to talk about her business in a way that would set her apart from her competitors.

What we all learned this year, is that $5,000 can be both everything and nothing to a small business. Which is to say a scholarship like this can completely change the course of your business, especially when you’re just getting started. But it’s also really easy to burn through that kind of money without even thinking. In fact, if there was one thing about Tristen’s scholarship application that stood out, it was that she was realistic about her expectations for the scholarship. Which always feels less sexy at first: who doesn’t want the reach-for-the-stars ideas instead? But that kind of realistic expectation is exactly what distinguishes the real-life business owners from the dreamers. (And I’d know, because I’m one of the dreamers. And it’s why my own business never had any money.) If nothing else, our mentoring sessions this summer proved that Tristen’s approach is exactly what made her the perfect recipient for our scholarship.

So a few weeks ago, Meg and I invited Tristen out for lunch near the APW office, for tacos and to talk about her experience this year:

RCG Education (1 of 1)

Meg: I was so excited about doing the scholarship and then we picked the recipient and then I went on maternity immediately after. So as we approach the end of the year, I wanted to give readers a sense of how it went, and what happened. What was it like finding out you were getting the scholarship?

Tristen: It was awesome. I kind of applied on a whim. It was a week before I delivered my baby, it was the one last thing to try. I assumed I wasn’t going to get it, but the exercise of applying was really helpful. What are my goals? What is my vision? What are my challenges? So even just articulating that was really helpful, money aside. I’ve been doing this a couple of years. I know how to make a business. What I don’t know is where to go next. And so it was the mentoring that was really invaluable.

Meg: Looking at the applications, I was surprised that the question that people had the hardest time answering was, “What would you do with the money?” I find that really interesting because early on in my business $5,000 would have been such a game-changer. To do justice to past me, I wanted that money to be meaningful for the recipient’s business. And so many people were like, “I’ll just use it for stuff…”

Tristen: One of the things I plan to do, that I haven’t done yet, is buy iPads. I’m also trying to get to the point where I can add more scholarship kids to our program. I started volunteering a few years ago with San Francisco CASA, doing a summer reading program with some of the kids, and it has been huge for them. But it’s very small and I can’t really scale it, because they can’t pay anything and it’s just me doing it. And even if I were able to find instructors to do that instruction for me, I’d still have to pay them. So the thing I was running into is, you know, luckily I have a very low overhead business. I don’t have a facility. I have a few books. But I work out of the library. And that’s all fine. But I’m cash in, cash out. So when I’m hiring someone, that’s a real challenge. Because during training they’re not adding any value to the business yet. They’re just watching me. And I have to pay them for their time. And since instructors need to spend several weeks observing and co-teaching, I end up taking a 40 percent pay cut for every hour I spend training new teachers. Not to mention fingerprinting, background checks, all that stuff. I’ve hired two people in the past and had to cut the training kind of short because I couldn’t afford it. And I knew they were not totally ready. I wish I’d had a few more weeks with them. But I just couldn’t swing it financially. So the money itself is allowing me to do the kind of training I’ve been needing to do for years. Instead of training being dictated by what I can afford to do, it can now depend on instructor readiness. Calling this a game-changer is a dangerous understatement.

Meg: That’s amazing. So have you made any new hires yet this year?

Tristen: Well…

Meg: Employing people is hard.

Tristen: It’s been so hard! I had someone lined up that was supposed to start November 1. She was finishing up a writing residency in Iceland, which is fantastic. Then she met someone. And I can’t blame her for falling in love in Iceland and staying there. But I was so excited to tell you guys that I’d done something with the scholarship money, that I’d found someone. And now that’s not happening.

Meg: We’re finding the Bay Area hiring market really tough right now. One of the things we’ve seen is people saying things like, “Well, I have this entry-level job in tech for a hundred thousand dollars. Can you match that?”

Tristen: I broke my back for years to make less than that. So the short answer is no.

Meg: Also, I was talking to a photographer, and the other problem is feeling like you need to pay people something where they can afford to rent. Can you afford rent if you’re making less than a hundred thousand dollars a year in the San Francisco right now? Maybe not, sadly.

Tristen: Well now I’m scrambling to find someone. Because this is is my busy season. It’s back to school, the SATs are changing in March, and all these things are kind of looming on the horizon that I had hoped to have someone on board and ready to help with and that’s no longer the case. So one of the things I hope to bring up in our next mentoring session is… what do I do? How do I find these people? And I understand, because it’s a really non-traditional role. It’s afternoons, it’s not many hours (though the hourly rate can be good), but I’m finding two main types of applicants, which are retired people who need to make more money, but don’t like it, or really passionate recent college grads who have never taught in their lives.

But the money isn’t going anywhere in the meantime. When I find the right person, it is such a relief to know that I now have the resources to give them the kind of training and support that they, and the students, deserve. It has also motivated me to put together some more formal training materials, which will hopefully streamline the whole process and prove relevant for any future hires.

Meg: It sounds like, even with the scholarship, you’re still figuring things out in this insane Bay Area economy right now.

Tristen: Yes, but I also haven’t spent a lot of it.

Meg: Well, and Maddie and I talk about this often, but one of the things, other than people skills, that sets apart a good CEO or business owner, no matter how big or small it is, really comes down to how good you are with managing money. And by managing money I don’t mean, like, earning interest. But making smart allocation decisions. And what Maddie often points out to me is that is not everyone’s joy in life.

Tristen: Like me.

Meg: But if you weren’t good at it, you would have spent all the money already.

Tristen: But I agonize over it. Though I find that the best things that I have spent money on in the past are about making sure I stay smart. Reading books, going to conferences, making sure I carve out an hour of my day just to make sure I end it smarter than I started.

Meg: I feel like I haven’t been doing that. That’s brilliant. Unrelated: did you make a new site with Squarespace yet?

Tristen: I did!

Meg: How was it putting together a new web presence?

Tristen: Good! I learned that less is more. And I suspected this even before we spoke, but I suspected that I was talking as though my audience was fellow educators. And that’s not the case. So I had to pare it down a little bit. And I feel like the images are speaking to that more than the words ever could have. And that has been really helpful.

Meg: The Internet has a two second attention span right now. So most people’s reactions are, “Does this look professional? Is this a good fit for us?”

Tristen: Not to mention the fact that my old photo didn’t even look like me. So when I’d meet people they’d be like, “Where is this girl?” They’d be looking at their phone like, “Is this the same person?” And you know, speaking of photos, it’s worth repeating that I have always thought of myself as a teacher first and business owner second/third/fifth. I have worked hard to earn the confidence I feel in my classes, but I have never had any formal training in business and have just been making it up as I go along. Getting connected with other business creatives like yourselves has been invaluable. Even if I’m just following Sarah Deragon (who did my new headshots) and Lauren Caselli on Instagram, it feels like my network of smart lady-friends has expanded significantly.

Meg: Is there anything else you want to say about the scholarship?

Tristen: I’m almost embarrassed to admit this, but the scholarship is helping me take myself more seriously. Sometimes I’ll wake up and be like, “Tristen! You have a master’s degree! And you’re a fucking tutor?” And even though this is the kind of external-validation-thinking I tell my students to rise above, it does sometimes get the better of me. Maybe it shouldn’t have, but this scholarship has given me a reason to recommit to myself, and to my business. It’s easy to let that hour of my day I’ve committed to getting smarter get squeezed to forty-five minutes, or thirty, or zero, especially when my students are frantic and my inbox just won’t quit. But in the past, I’ve never regretted the sacrifices I’ve made to stay on top of my game, and this scholarship is helping me do that with even more conviction. Sometimes that means shelling out for a conference, sometimes that means subscribing to journals, sometimes that just means listening to the New Yorker fiction podcast while I pump in the car on the way to work. Regardless, it always means time, and this scholarship is inspiring me to make sure I take it, and opening the doors to professional development opportunities that felt previously beyond my reach.

On a more personal note, this scholarship came at just the right time. When I was six months pregnant, my mom was diagnosed with a very aggressive, late-stage cancer, so I spent the last three months of my pregnancy and the first three months of motherhood camping out in various hospitals, doing lots of crying, and having a hard time caring about much else. I wondered, not entirely without reason, if I might go out of business. Thankfully, my two current employees, Christopher and Lee, were amazing, and four days after my mom died, I found out I won this scholarship. It seemed like the universe was reaching out a hand to me right at the moment I was tempted to turn my back.


This post was sponsored by Squarespace. A huge thank you Squarespace for making this scholarship possible, and our dream of supporting #PinkEntrepreneurs a reality. The Squarespace mission is to provide creative tools that give a voice to your ideas, and a home for your business. In conjunction with the APW + Squarespace small business scholarship and our #PinkEntrepreneurship series, Squarespace is offering APWers a 10% discount on yearly subscriptions when you use the code APW15 at checkout. Click here to get your business website started today with a free 14-day trial from Squarespace.

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