Season 2 Episode 7
Charles Best, founder and philanthropistWhy staying true to your purpose and values is essential for greater business success

Charles Best is a philanthropist and the founder of DonorsChoose. While working as a teacher, he’d be met with the same challenge over and over again: how can teachers raise funds for the supplies and projects they need or desire? He’d soon develop his crowdfunding nonprofit to help teachers and classrooms nationwide.

Tune in to hear how Charles applies his purpose and values at every step — from choosing a business model and managing fulfillment through improving hiring and gaining the ideal celebrity supporter.

Charles Best was a school teacher when he decided to find a way to fund teachers’ dream projects, class trips and essential school supplies. As DonorsChoose scaled over time, Charles learned a series of lessons that would continually reconnect him with his “why”.

His purpose and values have impacted everything from how they chose the right business model, how they guarantee quality fulfillment, their process designed to identify the right hires and even how they secured the incredible loyalty of a celebrity supporter turned board member.

This is part two of our conversation with Charles Best. Check out part one of the interview if you’d like to catch up.

In this episode, you’ll hear Charles Best discuss:

  1. Choosing a business model that matches your “why”
  2. Managing fulfillment to guarantee integrity
  3. Financing the operations of a non-profit organization
  4. Fine-tuning your recruiting process over time
  5. Hiring based on values
  6. Getting excited about the art and science of sales
  7. Testing new tactics to improve your results
  8. Rapid-fire questions

Choosing a business model that matches your “why”

Chris Allen: We’ve talked about the three innovations: your digital marketplace, cause marketing and then crowdfunding. But something I’d say is really unique is that it is a nonprofit. When we say marketplace, we’re really talking about where there are two parties coming together to converge to do something together somewhere like app stores and Kickstarter, typically to buy or trade. So why did you pick nonprofit and how did you build the team and fund the business?

Charles Best: Yes. Well, I think the reason why we needed to be a nonprofit instead of a for-profit company is that when DonorsChoose grew and started to generate serious earned revenue, and was the equivalent of a highly-profitable charity, plenty of people asked if we would consider converting to a for-profit or why we were not a for-profit, but we wanted to be a nonprofit from the beginning.

And we’re committed to being a nonprofit, because we want to do something that to a lot of investors doesn’t make economic sense. And that is to be the place for a teacher in a low-income community to be discovered by donors whom they’d never met. And to channel the majority, the overwhelming majority of dollars flowing through our site to public schools in low-income communities. If we were out trying to strictly unlock venture funding to be the most profitable company possible, we probably should focus on being the wallet through which a middle-to-upper income parent donates to their own kids’ classroom.

Chris: Gravitate towards the affluence.

Charles: Exactly. Exactly. That’s what we would almost feel a shareholder obligation to gravitate toward if we were a business, a for-profit, because it makes more financial sense to target that market. There are reasons even beyond unlocking revenue and sort of the size of the addressable market. There’s also a major cost involved in being the means for teachers in low-income communities to get discovered. If you are an upper-income parent donating to your own kids’ classroom, you don’t actually need a whole lot of integrity controls because you can see when you drop your kid off at school that when you donated $10 toward a projector, they really did buy a projector. And there it is in the classroom being well used. And in that context, the mechanism that you’re using to donate can probably just be a cash pass-through. It could probably just deposit money into the teacher’s personal bank account. And we can trust that things happened as promised because the parent can actually monitor the projector the next day.

Managing fulfillment to guarantee integrity

But in our case, when we’re talking about strangers giving to classrooms where they’ve never set foot, we need a whole host of integrity controls. We vet and authenticate each teacher’s project request before it’s posted to the public site. We email follow-up questions to the teacher. We do fact-checking. Only then does the project see the light of day, when the teacher’s project is funded. We do not pass through cash to the teacher and just trust that things are going to happen as promised. We purchase the resources and have them delivered to the classroom.

So even if it is therapeutic horseback riding for three students with disabilities, we are paying the horseback riding stable, which is providing that service to those three students.

Chris: Oh my goodness.

Charles: If it’s a field trip, we’re paying the bus, we’re paying the museum. If it’s butterfly cocoons, we’re paying for butterfly cocoons to be shipped to the right classroom. Once the butterfly cocoons were shipped to the DonorsChoose office and a whole lot of butterflies hatched. And that was actually grosser and dirtier than you think. It evokes magical, fantastical, fairytale butterflies flying all around, actually butterfly cocoons are kind of dirty in any case. And then after.

Chris: So that’s managed fulfillment.

Charles: Yes. Very managed fulfillment.

Chris: Which is a white-glove heavy resource.

Charles: Exactly. Exactly. And finally, after we have fulfilled the project, we provide a means for the teacher to send in thank-you letters from students. The teacher takes photographs of the project in action. The teacher sends in a thank-you note and an impact letter describing what’s happening, thanks to the donations. All of that needs to be vetted for child safety. And the short of it is we do a heck of a lot of work on each project request so that a donor who’s never set foot in a classroom can feel 100% confident that their donation is being spent as promised. They can see how every dollar is being spent.

They can hear back directly from the teacher and students. And it’s only thanks to that integrity and transparency and accountability infrastructure that we can actually inspire folks to donate to teachers they’ve never met before. And to students who aren’t in their families. And of course that adds cost to our model, and we’ve figured out how to make all that work scalable. But it’s just another example of how the mission that we have set forth of being a force for equity in education doesn’t always make business sense. And that’s why we’re a nonprofit.

Chris: Which is a powerful message. And I think managed fulfillment provides security. That experience that you just described is probably also a really great invitation for not only teachers to post again, but also to think big.

Charles: Yes.

Chris: Because they’re like, it’s going to take a lot of time. I’ve got to do all these things.

Charles: That’s right.

Chris: I’m going to put bigger projects on and not the $50 for some markers for everybody.

Charles: That’s exactly right.

Financing the operations of a non-profit organization

Chris: You said it’s resource intensive: it takes a lot of work, there are people involved, and it’s white-glove service. So how do you fund the business of DonorsChoose?

Charles: When someone gives to a classroom project request on our site, let’s say, by the way, Chris, what would be the passion that you would express on DonorsChoose? Is it a particular book that you loved to read or a sport you played in high school or a hobby that you have or a place, a town in America that you feel a lot of heart for? What would be yours?

Chris: I have a soft spot for musicians.

Charles: OK.

Chris: Yeah, so kids trying to learn new musical skills.

Charles: So if you did a search for Denver music project requests on our site, you’d probably have a few to choose from. If you pick one from a Denver teacher who is requesting violins for three of her most promising students, and that project costs $1,000, let’s say you commit to give $100 to that project. You’d be encouraged, but not required, to allocate 15%, or in this case $15 of your donation to support the work that DonorsChoose does. About 85% of donors keep that 15% optional allocation included in their donation. And the income thus generated is our operating income. And that’s the money that we use to pay salaries to keep the lights on. For the first 10 years of DonorsChoose, that operating income was not sufficient to pay our bills, so we had to seek outside operating support.

In year 10, we broke even. There were enough people giving to enough classroom projects, including that 15% enough of the time that the revenue thus generated paid all our bills. Today we generate millions of dollars in operating income over and above our operating expenses, meaning we’re the nonprofit equivalent of a highly-profitable organization. And we deploy all of that — I don’t want to use the word “surplus”, because we actually feel it’s very vital, but the money that we bring in over and above our operating expenses, we put it all back into classroom projects in really strategic ways. If you’re a teacher in a low-income community posting your first project, we match all the donations to your first project. The money to do that comes from that operating surplus.

Chris: Do you do capital expenditures out of that too, since operating income comes out of it?

Charles: We do. We do.

Chris: OK, so that makes sense. So if you need infrastructure changes or other capital expenses, you can pay for it out of that money.

Charles: That’s right.

Chris: OK, that’s cool. So what did you do from all the way up to year 10 before you broke even? How did you get the balance of your operating income to cover your expenses?

Charles: We did something that was very similar to what a tech startup might do or even a business that is looking to grow. In year five, we put together a plan for going national, for opening up access to all of the public schools in America. And our commitment was if we can get a $14 million infusion of operating capital, we’ll be able to build the tech infrastructure and the people infrastructure so that DonorsChoose can go national.

And when we do, there will be enough people giving to enough classroom projects, including that 15% enough of the time that DonorsChoose will break even before that $14 million runs out. And in fact, $6 million of that $14 million is still sitting in our bank account because we broke even before that kind of Series A ran out. That’s not a typical approach for a non-profit, it’s really the approach that a business would take. But I think it was a compelling proposition and it sure gave us a sense of urgency: “We’ve got to break even before this $14 million infusion is spent.”

Chris: All right. Were you teaching during this time?

Charles: I taught for five years. By my fifth year of teaching, I felt like I risked not being a good teacher because I was yammering on my phone in between every class break and racing out the door when the school bell rang and no longer hanging out in the teacher’s lunchroom with my colleagues where the idea for DonorsChoose came to be. So I taught for five years and then from year six onward, it was DonorsChoose full time.

Fine-tuning your recruiting process over time

Chris: Wow. OK. So talk about the leadership team during the time when you decided to raise this $14 million. Who was on the leadership team with you when you went to raise that money?

Charles: A group of people, most of whom are still with DonorsChoose. I did make more than my share of hiring mistakes in maybe the first five, 10 years of DonorsChoose. But I’d like to think I learned from them. And I think the caliber of the DonorsChoose leadership team and really at every level of DonorsChoose, reflects that learning. We have a really long tenure and we actually tend to recruit from former teachers who used DonorsChoose. That’s a profile we love to recruit from. We recruit even more from folks in the business sector who maybe have thought about joining a nonprofit because they want to do even more good for the world during their workday, but who don’t want their business acumen or their tech savvy or their data prowess to soften or to atrophy and DonorsChoose is a magnet for those people. We tend to recruit from the business sector, folks who can see that the caliber of the DonorsChoose team, the strength of our tech stack, the focus we have on data, our obsession with customers and customer service could go up against a top Fortune 50 company.

Chris: Well, it takes a really interesting collection of people, prowess and dedication to do something that changes behavior, because that’s the hardest thing to do. It takes a real culture to do that. Tell us a story about how you realized you needed to modify your hiring and recruiting techniques.

Charles: I think in the early days, especially in the tech arena, I was wowed by pedigree, by academic background, by sort of formal credentials. If someone had a Ph.D. in computer science, I thought, oh my gosh, they have a Ph.D. I’m supposed to address them as “Dr. so and so”. They must be amazing. And there’s not a whole lot of correlation between having a Ph.D. in computer science and being a great manager or leader. There might be a decently-positive correlation between that academic background and being a good individual contributor coder, maybe. But there might not be any correlation between that and leading people. That was a big learning for me. Another was that this—

Chris: Well, you appreciated education too.

Charles: Yes.

Chris: So I could see how that’s like, “Oh man, this person’s committed.” And then it’s like, “Oh, but they may not know how to lead people.”

Charles: That’s right. That’s right. That’s right. I think we also learned that it’s OK to interview not just for cognitive horsepower and inventiveness and work ethic, but to also interview for humility and to interview for an attitude of gratitude, which is something that we try to exemplify at DonorsChoose and model as well as in our people.

Hiring based on values

Chris: So that’s the thing I find really, really powerful: when businesses are values-driven. Talk to us about the values of DonorsChoose and how you screen people with those values.

Charles: I’ll give you one example of an interview question that we sometimes ask and the interview question is, who are you grateful for? About half of the candidates immediately mention their mom and then can’t name anybody else. And we think that the ability to rattle off the coach in high school who meant so much to you, the former boss you had at your last workplace who taught you this and that, the ability to rattle off people who you feel a sense of debt to is so indicative of the kind of person you want to work with. And not just an attitude of gratitude, but humility, thoughtfulness, ability to give credit where credit is due, a lack of a sense of entitlement. It captures a lot, that question. And it’s kind of wild how many people cannot go past their mom when we ask, “Who are you grateful for?”

Chris: That is a ridiculously-insightful question. I love that one a lot. Can I steal that one?

Charles: Totally.

Chris: OK. I like that one. Because instantly, I’m sitting here thinking, “How would I answer that question?” There really is something to be said for knowing that it wasn’t you alone that got you somewhere — even through your own grit, effort and dedication. Those things matter, and your values definitely get you somewhere, especially if you have achieved success. But the amount of people who helped you do what you did, helped instill those things in you, helped refine those things in you, helped foster those things around you, helped create environments when you didn’t even know that’s what they were doing. And that’s the power of mentorship. That’s the power of coaching, and the power of all those things. It is so important to be able to think, “This is happening for me and to me,” and to be like, “I appreciate it.”

Charles: That’s right. That’s right.

Chris: It’s a powerful thing. That’s really insightful because you just asked a question that showed what’s in someone’s heart really quickly.

Charles: That’s right. That’s right. That’s right. I’ll give you one other interview question, not quite as fun as who are you grateful for. But we like to identify a passion for learning, for self-improvement. And one way to get at that, at the beginning of the interview, people usually say, “Walk me through your resume and tell me, give me the voiceover of what you’ve been up to over the last five years, 10 years.” And we’ll say, “Hey, instead of walking us through what you’ve done over the last five, 10 years on your resume, tell us what you’ve learned…one thing you’ve learned at each stage of your career,” and most people cannot do that pivot. They have their stump speech about their career over the last 10 years and they’re not trying to come off of that at all. And so it’s actually a fraction of people who are able to hear that you want them to do something different walking through their resume and actually pivot to saying, “Here’s what I learned at each of the jobs I’ve had over the last few years.”

Chris: I mean, basically those two questions right there reveal someone’s willingness to be vulnerable. And that says a lot about their willingness to connect and be somebody who you’re like, “I could get into the foxhole with that person and we can go to righteous war to raise as much funds as we can for the people we care about.”

Charles: I never thought of the common thread as a willingness to be vulnerable, but I think you nailed it.

Getting excited about the art and science of sales

Chris: Those are super practical things, and I think the culture is really powerful. You seem to be somebody who can pitch. And that doesn’t come very naturally to people. But one of the things that I’ve noticed with either small businesses or entrepreneurs or startups is that there is often a perception that when you’re a consumer, you’re like, “Here are the things that drew me to something.” And it’s like, “I was walking by a restaurant and so I walked in, gave it a shot, or somebody recommended it to me.” And I think that the art of attraction is totally different than when you become a business owner or an operator where you’re no longer a consumer. And you have to think, “How do I get that initial traction?” So if you were to talk to a group of entrepreneurs or a group of people operating non-profits, what would you say are some keys to be able to find your story or your hook? And what are the ways to reach outlets to share those stories?

Charles: Well, first what I think you’re making clear is that if you’re going to be an entrepreneur, a small business creator, you need to see sales as the art and science of getting to yes. You need to see it as the thrill of the chase. I think the vast majority of folks out there feel that sales is undignified on the ask side of the table. They think that you’re soliciting, that you’re coming with your hat in your hand and asking for something. And I don’t see it that way. I see it as the thrill of the chase, and I think you need to see it that way to be an entrepreneur or a small business owner.

And yet, I think there are a lot of people who think that the art and science of getting to yes is just about how charismatic and persuasive and eloquent and energetic you are when you’re making a pitch. And I do get energetic and excited about what we’re working on. Hopefully, you could feel that right now.

Chris: Oh, it’s effervescent.

Charles: But I’ll give you an example of how we got Stephen Colbert involved with DonorsChoose, because he has become in many ways our hardest-working board member. He gives a DonorsChoose gift card to every guest who goes on the late show.

Chris: That’s awesome.

Charles: He has done stunts and campaigns and calls-to-action that have generated tens of millions of dollars in giving to projects on our site. And Stephen Colbert got engaged with DonorsChoose in 2008, when he was running for President in the South Carolina Democratic primary basically as a joke. And we sensed, as he was doing this run for the presidency, that he had a problem on his hands, which is he had all these fans and viewers and followers who wanted to support his campaign financially, but Stephen himself would not actually want his viewers to part with their hard-earned money for something that was an act of satire, for a joke. So he had a bit of a conundrum on his hands. So we came up with an idea for a philanthropic presidential straw poll on DonorsChoose where someone could donate to a classroom project in honor of their favorite candidate, and thereby push their candidate higher up in what we were going to call a straw poll that makes a difference. And we found a way to share this idea with Stephen through Craig Newmark, the founder of Craigslist, who was someone who had said yes to coffee with me when I emailed him cold, out of the blue. He didn’t know me from Adam.

Chris: Wow.

Charles: This was year two of DonorsChoose. But he was like, “All right. Yeah, sure. I’ll have coffee with you at Cole Hardware store in San Francisco next time you’re in the city.” And we knew he was going on The Colbert Report, so we were like, “Hey Craig, we’ve got this idea for a philanthropic straw poll.” And the wife of Jonathan Alter, that Newsweek editor who had done that first paragraph, his wife was working at The Colbert Report, so we had a second angle in as well. We got the idea to Stephen Colbert, and it turned out that’s exactly the kind of thing he was looking for as the way for his viewers to step up and show their love. And he called upon his viewers to make him the winner of the DonorsChoose straw poll that makes a difference. He inspired tens of thousands of dollars in donations to South Carolina projects on our site, and that was the beginning of the most deep engagement we could ever ask for from a celebrity supporter.

The lesson here is that we didn’t go to Stephen saying, “DonorsChoose is a great cause. You ought to support us because we’re great.” Instead, we went in saying, “Hey Stephen, we sense that you have a challenge on your hands. We sense that you have a bit of a problem to solve. Our organization can be a means for you to solve that problem and overcome that challenge that you’re facing. And oh, by the way, we’re a good cause.” But I think that approach of your organization, not as this wonderful thing unto itself, but your organization as a means for somebody to solve a problem that they have where you’re showing that this pitch is specific to them. You’re not coming in with your standard stump speech. You’re saying, “Hey, after learning about what you are doing, I sense that you have this challenge. Here’s how my company, my organization, my product, could help you solve that challenge that I sense that you have.” That was our sort of unlock for the most important celebrity supporter we have.

Testing new tactics to improve your results

Chris: That is amazing. And it is clear, right? There’s a theme that you are really great at recognizing good intentions with problems in the way. And I think unlocking that’s a real gift. What’s the other A/B test story that you said you were going to tell me?

Charles: About eight years ago, our CFO came into the office having just read a book called Drunk Tank Pink by this NYU business school professor, and the book cited research that people are more likely to donate to hurricane relief if the first letter of the hurricane is the same first letter as their own name.

Chris: No way.

Charles: And apparently this effect is so pronounced that the U.S. meteorological survey has left half a billion dollars of hurricane relief on the table by not giving the most severe hurricanes common first letter names, and thereby inspiring that much more hurricane relief giving. So our CFO comes in our open office citing that research, and I overhear him sharing it. And I’m like, “Wait, we should do something with that research insight. We’ve got hundreds of thousands of teachers and millions of donors, we can match them up maybe by name.”

Valentine’s Day was coming up, so we did an A/B/C multivariable, concurrent test. We sent three variations of a poem. The first poem read, “Roses are red, violets are blue, we heart this teacher and hope you do too.” And underneath that poem that we emailed to a randomly-selected third of our donors, we would show a classroom project request that was algorithmically selected just to be compelling. Maybe it was from an especially high-poverty public school, not needing very much money to cross the finish line, from a teacher who’d never been funded before, that a lot of other donors had given to, a really compelling project.

Chris: Popular scenarios.

Charles: That’s right. So that was Test Flight A. Test Flight B read, “Roses are red, violets are blue, give to a teacher in a classroom near you.” And underneath that poem, we would show a classroom project request targeted to your IP address or to your billing zip code: “Here’s a classroom near you.” And that should be the holy grail of personalization, right? Hyper-local geo-targeting.

Test Flight C read, “Roses are red, violets are blue, give to a teacher with the same name as you.” And underneath that poem, we would show you a classroom project request from a Mr. or a Ms. Allen. And if you had an especially common last name like Smith, then we would key off of you having the same first name as the teacher because we would want it to feel a little bit idiosyncratic OR? I wouldn’t be telling you this story.

Chris: Tell me. Come on.

Charles: If it wasn’t obvious which test flight proved most successful.

Chris: Yeah, there’s 10 points to put in each bucket. How many points went in bucket three?

Charles: Yeah, exactly. You should put all of them in bucket three because there is something far more powerful than hyper-local geo-targeting, and it is name matching, which led to a far higher conversion rate than either test flight A or B. And one thing we further believe is that there’s something even more powerful than name matching, which is birthday matching, right? You meet somebody at a party who shares your last name, you do a quick check to see if you’re extended family. OK, you’re not. You’re moving on. Nothing more than a fun coincidence that you share the same last name. You meet someone at a party who shares your birthday and you’re like, “Oh my gosh, we are kindred.”

Chris: Totally. We may have been in the same hospital on the same day.

Charles: Exactly. Exactly. We may share personality traits, if you’re into that kind of thing. And so we optionally invite teachers and donors to share their birthdays. And we believe that perhaps the single most effective email, system email, that we send is to a donor on their birthday where we say, “Hey Chris, happy birthday. Wishing you well. And PS: here’s a classroom request from a teacher who shares your birthday, who’s also celebrating their birthday today. And here’s a $10 DonorsChoose gift code as a birthday present to you, Chris, that you might want to spend on this teacher’s request who’s also celebrating her birthday today.” And you can imagine that there’s a fair number of people who don’t just spend that $10 gift code but decide to add significantly to that donation.

Chris: That’s amazing. There’s the sale of the gift card and there’s the purchase, the person buying. And typically, people who have gift cards spend X amount of dollars more, and in restaurants and retail, it’s up to like 75% more on average.

Charles: Wow.

Chris: So what was the average that people would spend over the $10 gift card?

Charles: Our general rule for gift card ROI is probably not quite as good as the restaurants you were just citing. What we tend to see is that on a people basis, we see a discouragingly small number of people add their own money. But of that fraction who do, they tend to add so much of their own money that it does create a super positive ROI.

Chris: That’s awesome.

Charles: For the gift card distribution, it’s more like maybe 5% or even 1% are opening up their own wallets, but they open them up. We had one donor who to date has given more than $1 million, who was acquired with a $10 DonorsChoose gift code.

Chris: Man, that is amazing. Wow. On average, it’s probably really high then.

Charles: That’s right. On a dollars basis, it’s a very positive ROI.

Rapid-fire questions

Chris: Well, that’s really powerful. So it seems to me that you definitely recognize problems quickly and can recognize solutions that match people’s interests. I don’t know if that’s learned or if it’s a superpower, but it’s really powerful. It’s been incredible to listen to your story and to hear about all of the things that you’ve been able to accomplish.

I want to ask you some rapid-fire questions and then ask you what’s next for Charles Best.

Charles: Let’s do it.

Chris: All right. Question number one: what’s a must-see spot in NYC that’s off the tourist map?

Charles: There is a broccoli rabe hoagie at a spot in Hunt’s Point in a very industrial neighborhood of the South Bronx that I was taken to by a guy named Famous Fat Dave, who was a taxi driver for years for the purpose of asking every passenger in his taxi, “What’s your favorite place to eat?” And he would just collect all of these tips and he will take you to the Irish place in Queens that makes the best roast beef sandwich. He’ll take you to the spumoni place where they use pistachios to create ice cream. He will take you to the place where you can get a fried Twinkie.

Chris: Unbelievable.

Charles: He will take you to the most interesting places. And actually I think my two favorites were jerk shrimp, which was a stop off in the Bronx. And then broccoli rabe gyros, which was not a sandwich for vegans. It’s like a grubby, delicious truck driver’s version of broccoli rabe gyros.

Chris: I love it. Do you still have this person’s contact information?

Charles: Famous Fat Dave. You can look him up.

Chris: All right. That sounds good. So would you describe yourself as a thinker or a doer?

Charles: Doer.

Chris: What are you most excited about?

Charles: I’m excited about tacos in LA.

Chris: OK, foodie. All right. Famous Fat Dave. Is that what his name was?

Charles: That’s right. That’s right.

Chris: And then what’s a major adjustment that you’re anticipating?

Charles: I didn’t get my driver’s license until I was 22 because I grew up in New York City and I walked and took the subway everywhere, and so driving every day in LA is going to be kind of new for me.

Chris: The 405.

Charles: That’s it.

Chris: What was your favorite historical period to teach?

Charles: Oh, I loved the Gold Rush. I loved teaching on it and I loved researching it in college.

Chris: Wow. Well, what’s one historical figure that you’d want to have dinner with?

Charles: I’m going to say Harry Truman because I read his bio and he just seemed like the most standup guy who people had low expectations of and who smashed those expectations.

Chris: Who is another entrepreneur who inspires you?

Charles: Ooh, a whole bunch, but I’m going to say, and this could be a segue, a woman named Ethelyn Kaplan, who was a single mom, who in 1954 opened her own toy store on Lakeshore Avenue in Oakland, and saw a lot of teachers coming in to her toy store and saw, “I need to become the place for teachers and then principals and schools and nursing/nursery schools and preschools, to get what they need to furnish their classrooms and it would become Lakeshore Learning.”

Chris: All right. Well then, what’s next for you?

Charles: Yeah, so about two years ago, I passed my 20th anniversary at DonorsChoose, and I was having as much fun as ever, learning as much as ever, but I just knew I’ve got to pass the torch at some point. And if I can’t resolve to do that on my 20th anniversary, then when the heck am I going to do it? So I resolved to pass the torch. I was able to recruit the dream candidate, who I’d had in mind, a guy named Alix Guerrier, who’s incredible. And I passed the torch to him last spring, joined the board of DonorsChoose, and spent some months researching some ideas and some fields.

And then much through serendipity, I found myself talking with a guy named Bo Kaplan, who was Ethelyn’s grandson, and he had this vision for my joining Lakeshore Learning. And I recognized it as the most incredible opportunity for me to go from crowdfunding the learning materials that teachers most want for their students to making the learning materials that teachers most want for their students.

Chris: Wow.

Charles: And it’s at an even bigger scale than DonorsChoose, a much bigger scale than DonorsChoose, but it is still the same effort, the same arena of equipping and enriching classrooms all across this country.

Chris: Man, it’s going to be powerful. I have to say. And you’re still on the board of DonorsChoose?

Charles: That’s right.

Chris: Yeah, which is amazing. Well, I have to say, your enthusiasm, your level of, I’m going to say give a sh*t, is so high, and it’s really incredible to just sit across the table and just hear all of the things that you’ve done, all the problems that you solved. And it means a hell of a lot that you came and sat and had a conversation with us at the studio.

Charles: Oh my gosh, Chris, thank you so much. Your questions were really some of the sharpest I’ve ever been asked, I think because I’m talking to a fellow entrepreneur, so I’m so grateful.

Chris: Man, thanks for coming.

Charles: Thank you.

Chris: Wish you the best.

Charles: All right.


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