Entrepreneur and angel investor, Rei Wang is the Co-Founder and Chief Product Officer at The Grand, a group coaching platform to help people navigate transitions at the intersection of work and life.
Before The Grand she served as CEO of Dorm Room Fund at First Round Capital where she nurtured a community of 250+ startups, and counseled entrepreneurs on topics ranging from fundraising to management.
For her leadership growing Dorm Room Fund from an experiment into the world’s premiere university-focused venture fund, she received the Forbes 30 under 30 award in venture capital.
Entrepreneur and angel investor, Rei Wang is the Co-Founder and Chief Product Officer at The Grand, a group coaching platform to help people navigate transitions at the intersection of work and life.
Before The Grand she served as CEO of Dorm Room Fund at First Round Capital where she nurtured a community of 250+ startups, and counseled entrepreneurs on topics ranging from fundraising to management.
For her leadership growing Dorm Room Fund from an experiment into the world’s premiere university-focused venture fund, she received the Forbes 30 under 30 award in venture capital.
Intro: [00:00:00] From Silicon Valley, the heart of startup land, it's Getting2Alpha, the show about creating innovative, compelling experiences that people love. And now, here's your host, game designer, entrepreneur, and startup coach, Amy Jo Kim.
Amy: Rei Wang has been on both sides of the table as an investor working with hundreds of companies at First Round Capital and as an entrepreneur running her own company, The Grand.
And not surprisingly Rei's experience as an investor directly inspired the company that she now runs.
Rei Wang: After about four years of working at First Round, I took a step back one day and we're like, a lot of VCs provide this type of support to their portfolio founders. But what about everyone else in the world?
We're all navigating transition. So we thought about how do we actually create. A new platform for coaching that anyone can participate in when they're going [00:01:00] through these big monumental milestones in their life and in their career.
Amy: Join us as we talk about Rei's journey from a child who loved both art and science to an entrepreneur with endless curiosity about how systems work.
So welcome everyone. We are here with Rei Wang and we're going to talk about her fascinating journey. Through the world of entrepreneurship and venture and building out the grand world. Welcome, Rei.
Rei Wang: Thank you for having me, Amy.
Amy: I'm really excited to learn more about your story and how you got to where you are and really how you see the world.
Let's start by winding it back. How did you first get interested in, and then start working in design and tech?
Rei Wang: Yeah, I think I've really always been interested in the intersection of design and technology. A lot of it has to do with the way that I grew up. So I grew up with [00:02:00] my grandparent, my grandpa was a calligraphy teacher and my grandma taught science, right?
So from a very early age on, those were the two realms that I was in. And I loved. Both art and science and really wanted to do both. So throughout my entire kind of childhood, that's what I loved. I loved to paint and draw and sculpt. And then my parents also worked in science. I spent a lot of time with them in, in research labs, conducting experiments by their side from very early age too.
So as I was navigating my studies in college and my career, I think it was that idea of not just being able to aesthetically design something, but also thinking about what is its function and what is the impact that you can create, right? Which is where the intersection of design and tech come into play.
Amy: What kind of science did you parents do?
Rei Wang: Oh, so my dad is a molecular biologist and my mom is a [00:03:00] cardiologist and my first job, here's a fun fact for you, my first job when I was 15 was actually at Mass Eye and Ear Infirmary in Boston for anyone here who's from the East Coast and I did a lot of research with fruit flies, with Drosophila.
Specifically, I'm growing ectopic eyes, so external eyes on their wings and on their legs. And that was kind of my first introduction to science and got me really interested in thinking about kind of science fiction the way what does the future look like and how can we invent new things.
Amy: So you really grew up melding art and science together, it sounds like, and not having a one or the other approach to it in your family.
Rei Wang: Yes. I think my parents were definitely trying to sway me to go more science, but for me personally, I was also very interested in the creative side and the art and knew that I wanted to combine both of them.
Amy: So then you went to Emory.
Amy: Yes. How did you decide what to study when you were in [00:04:00] college?
Rei Wang: Honestly, I had a very hard time deciding. So I decided to pick the broadest major. So I ended up studying international studies. I was fascinated by world and culture and my specific major was around global culture and society. So definitely taking much more of a liberal arts, political science approach rather than going to technical, and I loved it.
I think for me, it really just helped me understand how do people relate to each other? How do societies and systems relate to one another and be able to think about the patterns and the systems that I might wanna be a part of in the future.
Amy: I love that you're bringing up systems. One of the things that I've noticed, I'm going to take a little side shoot here.
We teach a lot of basic systems thinking and systems design just through getting people to engage in creating a core learning loop or habit loop in our programs. And what I find is that some people are quite good at thinking in [00:05:00] systems. Many people aren't. So you work with tons of entrepreneurs and we're going to get there in a moment.
But it sounds like you very much thought how to deal with systems and how to see things as interrelated systemically in your education. Do you find that as you coach and oversee the coaching of hundreds and hundreds of entrepreneurs, do you see a difference between people that can think in systems and perhaps people that don't?
Rei Wang: Yeah, so I think putting my investor hat back on one of the questions that we used to ask founders when they would come in and share their business with us in a pitch is what is the biggest vision for what you're working on look like right in 10 years, 15 years, what could this be? And I think that's a really good question to see how people think about systems, because usually it's beyond just the product itself or the initial market that they're starting.
And it's important, [00:06:00] I think, for entrepreneurs to both be able to have a very grand vision of what their company could be, as well as a very specific entry point into the market, right? And an initial product that's solving a key problem. So I do think great entrepreneurs need to have the ability to both have that 10,000 foot view and define the vision and think about the system more holistically, as well as understanding the specificity of what they're working on and how to get there.
Amy: So, you had a pivotal experience in your career working at General Assembly. How was that? But even more interestingly, how did that shape how you think about education and training?
Rei Wang: I think what I loved about General Assembly, it was the opposite of academia in many ways. So instead of spending five to seven years getting a master's or a PhD in a specific degree, the General Assembly was all about learning by doing and really helping people learn a new skill set [00:07:00] in 90 days, right?
So you could argue in some ways that it was a much sort of scrappier method and it definitely wasn't perfect, but it gave people enough of a foundation to actually then go and start practicing that and start working and learning in their jobs too.
So, I also love that at general assembly, all of the instructors that taught the courses and the immersives were actual practitioners in the field, right? So as opposed to speaking from their work experience a decade ago, like most professors, They were able to bring in the real life products they were designing or businesses they were creating or websites they were building and be able to share that with the students and take them through that and think about how to problem solve together.
So for me, I really love that style of learning. I think when I was just starting at General Assembly, I was, gosh, how old, 20, 25, 26, maybe. And at that point I was really thinking, do I want to go to business school [00:08:00] or do I want to continue working at General Assembly? And for me, the decision was, do I want to learn based on case studies and sort of more theory, or do I want to learn by doing?
And for me, the learn by doing really fit my own personality and style more. And I jumped right in and took all the courses that I had to get my hands on, worked with our student community to really develop my own understanding of technology, business, and design too. I got the chance to build out a lot of new products at GA, which was a really fun and pivotal experience for me.
Amy: So you really honed your skills, sounds like, both as a learner, but as a product manager.
Rei Wang: Yes.
Amy: And then you moved on and you were the CEO of Dorm Room Fund. How did that come about?
Rei Wang: It came about the same way that this conversation came about, which was through the magic of Twitter. I think this was, this was when, this was 2015.
I was on Twitter one [00:09:00] night and I had been following First Round and the First Round review because they wrote a lot of great content that was relevant to my work as a product manager and I saw them that tweet that they were hiring someone to come in and lead and run Dorm Room Funds. At first, I never imagined myself really working in venture capital or finance, but I had clicked on the job description and read the JD and I was like, this sounds really interesting.
My work at GA and my work prior and one of my passions is community. And for me, community really means building in partnership with the members of your community towards a shared vision. Right. And I love Dorm Room Funds model and that they were actually enabling students to invest in each other. And I thought that was a really interesting way to both build community as well as build a site.
So it really caught my attention and I was thinking about it, but at the time, I felt, I felt very connected to New York. I'd been there for about [00:10:00] seven years. All my friends were there. I just bought a little apartment. So I was like, I don't know if I want to move all the way to San Francisco. For this role and a completely unknown industry to me, but I kept on thinking about it that night and I actually got out of bed in the middle of the night because I was still thinking about it.
And I was like, let me just apply and see what happens. So I sent a cold emails, uh, the partners at First Round. Introducing myself and why I thought I might be a good fit for the role. And then from there, everything actually happened pretty quickly. They got back to me. I went through the interview process, went out to San Francisco, got an offer, and then ended up moving to SF a couple months later with just two suitcases in hand to, to go on a completely new adventure in my career.
Amy: What was that like? And what were some of the things that you really learned the insights that you took away from that experience that you're carrying with you now?
Rei Wang: I would say the first six months was [00:11:00] completely like drinking from a fire hose. I had so much to learn and I'd do it really quickly. And after the first six months, I got a little bit more comfortable and I think definitely more confident in my own ability to build this fund and build this community.
And I think the biggest takeaway there personally for me is that I can try something new. And I have the ability to learn quickly and then be able to turn that into action, right?
So that was a personal learning. And then also another personal learning is a definitely cemented for me that I wanted to be an entrepreneur in the future. And I started to think about what that could look like for me in my career next. The other thing that I loved about working at First Round and about Dorm Room Fund was just the exposure that I got, which was amazing.
So for those of you who aren't familiar, First Round is a seed-stage fund based in San Francisco. They have about 250 portfolio companies that they had invested at the [00:12:00] time. And we're still doing dozens of investments every year. And then Dormant Fund is the first and the largest student run fund.
It's national and Dormant Fund had also made about a hundred investments and we were making roughly 30 investments per quarter too. So just the sheer number and volume of companies I saw. And industries that they were working in was amazing to see and gave me this broad view over what people were working on, but also what the future could look like and the themes that would take us there.
So I think having that exposure is something that I would always value and cherish. And again, kind of gave me that 10,000 foot view to think about what is everything look like as a system and what market and what space might I want to build in the future.
Amy: And then you launched your own startup, which you're running now.
So how did you come up with the idea?
Rei Wang: So First Round, as I mentioned earlier, really values community [00:13:00] and me and my co-founder Anita, we both did a lot of work at First Round to build community and to support entrepreneurs. And what we realized pretty quickly is the best ways to support entrepreneurs are Was not actually to tell them what to do or teach them through kind of off the shelf training or traditional workshops, but it was actually to connect them with each other and provide a small group environments for them to talk about the real challenges that they were facing, right?
So that's what is called group coaching in a lot of ways. And that was being most effective ways for the founders at First Round at Dorm Room Fund to be able to navigate their journeys as founders and to grow their company. So, we started bringing together these groups of founders regularly, creating the safe space for them to discuss their challenges to share learnings with each other and after about 4 years of doing that.
So, how [00:14:00] impactful it was for them, both professionally, but also really personally too, because so much of your journey of being a founder is tied up to your personal sense of identity and self worth. And that was a lot of the conversations that people were navigating. After about four years of working at First Round, I took a step back one day and we're like, it's really awesome that First Round, a lot of VCs provide this type of support to their portfolio founders.
But what about everyone else in the world, right? We're all navigating transitions. We spend about 50 percent of our life in transition, whether that's moving to a new city or taking a new job or becoming a parent, right? And for most of those parts, there are a lot of great places to go to figure out how to navigate those transitions.
You're kind of on our own, unless you happen to have a friend or family member who has done that before, too. So we thought about how do we actually create a new platform for coaching that anyone can participate in and find resources and support [00:15:00] when they're going through these big monumental milestones in their life and in their career.
So, So that's where the idea of the grand really came to be. And we started kind of concepting it and prototyping it at a small scale initially. And then from there built out the product and the tech to what you see today.
Amy: So you now have had this experience running a certain kind of group coaching at Dorm Room Fund, and then also launching and running a group coaching startup.
It's obviously, it doesn't always work, right? Like some group coaching is going to work better than others. I'm like, I've definitely seen that myself. What is the secret sauce? What is the magic that you've learned? That really makes a group coaching situation sing. And also what are some of the things that you've learned that will maybe result in a situation that doesn't work so well, that's [00:16:00] not quite as effective?
Rei Wang: Yeah. So the secret sauce is the group and you can't just randomly choose eight people that have nothing in common with each other and say, go be part of a group together, right? You really have to be thoughtful about who is in the group and what shared experiences they have with each other. So for us, our secret sauce is really thinking through their group curation thoughtfully.
And that's why for us, it's all about these transitional moments, right? So if you are a first time manager and we could put you in a group of other first time managers at fast growing tech companies, you're going to have a lot in common and you're going to be able to kind of help each other navigate those challenges, right?
Same if you are a first time parent, right? But as I put a first time manager with a first time parent, that, that's not really going to work because they're not going through the same transitional or the same experience. So I think for us, we spend a [00:17:00] lot of time getting to know each individual member that joins the grant, actually talking to them and learning about what is most important for them in terms of their goals and their intentions and their challenges, and then figuring out the right group for them to join and the right coach to work with them.
Amy: And what have you seen that can make a group go south? What are some of the things that you now try and watch out for, but that can really make it not so good?
Rei Wang: I would say first and foremost is commitment because part of the value prop is the group, right? You need a group to exist. So I think for us, something that we really stress in our dining principles, when we onboard every single member onto the grant.
Is we show up for each other that has to be there. You can't say, Oh, I'm too busy to join today, or I'm just not going to come today and not show up. If that's the case, then you're creating a negative [00:18:00] experience for everyone who was counting on you to participate. Right? So that's definitely something that we interview for is level of commitment.
And that's fundamental to the overall experience working well.
Amy: So, one of the things that I've seen in groups, and I'm really curious if you've seen it as well, beyond commitment. So first of all, I want to reinforce what you just said, which is a great group is going to have a shared role, a shared challenge that they're tackling, like first time manager versus first time mom, but also the first time part being really critical.
They're at a similar juncture in their journey. Yes. And so once you get a group like that together, that can be very promising. There's one other thing I've noticed occasionally pops up in groups, and I wonder how you deal with it or if you've seen it, which is you get those pieces right. You get the role right, journey right, you get the group going.
And [00:19:00] then occasionally there'll be somebody in a group who's just Fundamentally. Self absorbed or selfish more so than others, and they might be brilliant and sharing their struggles and offering advice, but they're there for what they can get out of it. And they don't have the impetus to be. Two way giving and one person like that can really mess up a group dynamic.
Have you ever seen that?
Rei Wang: I have seen that in the past, but less so in our grand experiences. And the reason there is I think we have really fantastic coaches that are amazing at facilitation. And they really try to create space for everyone to be able to both give and receive from the grant, right? And we have a lot of frameworks and exercises that try to balance how much, how much attention really every single person gets from the [00:20:00] grant and is able to share and create as much equity in the kind of the group dynamics as possible.
So, for example, we have a format called Clarity Council, where Every single time we run clarity council, there's actually 1 focus person who is invited to share their challenge in depth. And then the entire group gives their undivided attention to that focus person and ask open and honest questions to that focus person to help them really get unblocked from their challenge and find clarity in their answer.
Right? So, because of that format, it is 1 at a time and the coaches will track who's had the opportunity to be a focus person. And make sure it's not the same person every single time who is dominating the conversation, but that everyone really has that opportunity in the group.
Amy: Right. What are some of the common misconceptions that you run into about group coaching?
Rei Wang: Yeah, there's a lot of them, and I'm sure you've heard of them [00:21:00] as well. I think the first one is people think that group coaching is very similar to group therapy, and it's just a space for them to either vent or complain or let off steam, right? And that's actually not true. I don't think we're very explicit to define any time when we're talking to someone who is new to group coaching, right?
So as everyone here may know, coaching is really the journey of going from where you are now to where you want to be, right? So it's about understanding your present and then moving forward. towards that by taking actionable steps to become your future self. Therapy is much more about looking backwards and understanding your patterns and how that might influence your present, right?
So there's some overlap in that present, but for us, it's not just about sharing what's going wrong, but really thinking about What are the tangible steps that I can take to make progress towards the future that I want for myself, [00:22:00] my team, my company. So it is very proactive. It's very forward thinking, and this is about taking action rather than just getting something off your chest.
Amy: Yep. However, I have a question for you regarding that, because absolutely, as a group works together and gets to know each other and goes deeper, do you sometimes within the group deal with emotional issues as well that come up that keep someone from taking steps?
Rei Wang: Yeah, of course, definitely, right? I think the emotional is definitely connected to the professional and the personal.
And we do invite people to share, share their feelings and emotions that they have about a certain situation. But what we try to prevent…
Amy: …is in how you integrate and understand and strategize with research.
Rei Wang: Yeah, I saw that in your quote in the doc that you put together for me and I was excited to see it because I really love research and my partner is actually [00:23:00] a researcher.
So we talk a lot about the relationship between research and product, and I'm glad I have the opportunity to speak on this. So I would say research is really core to everything that we do at the grant, not limiting it to just those emotions and not having people be stuck in that. But really through the art of asking open and honest questions, helping them make progress towards that future self.
Amy: Yep. Now, something fascinating about your current role is that you're the chief product officer as well as a co founder. Yeah. And. In that role as the chief product officer, I'm really interested in how you integrate and understand and strategize with research.
Rei Wang: I really love research and my partner is actually a researcher.
So we talked a lot about the relationship between research and. Product [00:24:00] I'm not I have the opportunity to speak on this. So I would say research is really core to everything that we do at the grant, especially on the product side, right? So, as I mentioned earlier, one of my strong beliefs is really building in partnership with your community.
So we invite our community to participate in the product development process. Of course, the beginning, we tend to start with interviews and we really understand the pain points of our members as well as the coaches. Then with the product design and engineering team, we'll usually take a lot of that, start to kind of concept what we might build, create a prototype.
And then share it back with our community to try it and give their feedback and then from there iterate and then ship it to our community to use overall. So that's a little bit of our process, but it all is based on understanding the true needs of our community first in order to actually be able to build an effective product.
Amy: What form does your community [00:25:00] engage in? Did you roll your own platform, your own community platform?
Rei Wang: Yeah. So our community right now, they all live on Slack. So we talk to our community a lot on there and we actually have a channel called First Peek, where we invite the community to take a look at some of the early product concepts that we're working on and just be in conversation with us and share their ideas and feedback.
Amy: Awesome. So You have gone from eager student to working as a product manager, working, running a fund. Now you're a co founder and chief product officer of your own startup working to scale it. What are some of the mistakes? That you see first time product managers and product creators and product leaders make, especially entrepreneurs.
Maybe you made some of those too, but now looking backwards, you know that you have this knowledge and you see other people making these mistakes. What are [00:26:00] some of those common mistakes?
Rei Wang: Yeah, I would say for me, one, one mistake that I made, and I still sometimes get stuck here too, is being stuck in indecision for too long, right?
Especially when you're starting with more of a ambiguous problem, it can be really hard to know what do I test first or what is the right decision to make here? And I can get into a rabbit hole where I sort of talk myself in perpetuity into all of the pros and cons for each and the trade offs. And then from there, it's been many weeks and I haven't actually built anything or worked with my team to develop anything.
Right. And I think now I realize time is arguably my most valuable resource. And instead of like being stuck on figuring out which one is the right decision, just to trust I got and pick one and make an educated guess and hypothesis, And then actually create a concept or a prototype and test it. Give it [00:27:00] to a hundred users, give it to some of my community members and observe how they actually use it.
And that will tell me way more about whether or not this is the right direction to pursue than being stuck in my own head and trying to debate that.
Amy: That is such good advice. Don't know? Make a hypothesis, test it.
Rei Wang: Yes.
Get some data.
Rei Wang: Yes.
The tricky part is getting the right data.
Rei Wang: Yes.
But yeah, getting some data flowing in and then being honest with yourself about whether it's working or not.
Rei Wang: Yes.
So now let's turn our attention forward. What's your take of the coaching market now, but also looking forward over the next three to five years, what trends do you see?
Rei Wang: Ooh, that's a fun question. So I think overall the coaching market is going to grow exponentially in the next three to five years.
And the reason that I think [00:28:00] that is because I think as humans, especially given everything that we've experienced over the past two to three years, We are looking for a greater sense of purpose and fulfillment and meaning in our careers and a lot. And I think we want to work with coaches and with each other to, to find that meeting for ourselves.
So I think you're going to see an explosion of. All sorts of different types of coaching, everything from executive coaching to career coaching to spiritual coaching, right? So I think people really want a guide to help them navigate their own sense of self and identity. And you will see a lot more different verticals within coaching than we've ever seen before.
Amy: That's going to be interesting. Yeah, it's definitely one way to feel less alone and feel more connected to people that care about you, that can support you. Yes. [00:29:00] And one quick question, is all your coaching delivered online and remotely? It is. So we do it all online. Right. So that of course opens up the whole world to who's in your group.
Yes, it does. So switching a little bit to your really interesting double hat role as both an entrepreneur and an investor. It's a choppy market now. But people are definitely getting funded. One of my clients just got funded. Yay. But other people I'm working with are very much struggling. And there's this notion of default investable that's going around.
I'm sure you've heard it in the VC circles. So from your position, what do you think makes a startup Default investable in today's market?
Rei Wang: Ooh, interesting. I think that answer really varies depending on what stage you're considering the investment. So most of my experience is in early stage. So I'll speak to that and save later stage conversations for people who have more [00:30:00] experience there.
So I think at the early stage, what's different about the market now versus maybe the market a year or two ago. Yeah. Is it's not just about having that big vision and an initial concept. It's also making sure that you have strong business fundamentals, right? So a year ago, you could probably launch something and raise money.
If you had initial prototype or a product out a couple hundred or a couple thousand free users with a lot of traction and growth, I think that's still important now, but also showing that there's a willingness to pay and that you actually have a business model that. Makes sense is going to make you more investable than someone who hasn't thought about the business.
Amy: Yeah. That pendulum swings back and forth in startup land. It seems focusing on fast free growth versus focusing on business fundamentals. Right. So it sounds like the pendulum has swung.
Rei Wang: Yes. And I think right now you're in a tricky [00:31:00] place because you need both growth and strong business fundamentals.
Amy: Amazing. So here's a question. Let's say that you put an app together. You've got beta, there's a lot of promise. You're getting product market fit. You're deep in the thick of it, right? And. You need money in order to build it out. Maybe you don't have a lot of savings or there's other kinds of expenses.
What are some ways, other than a bank loan, that you've seen work to raise enough money that you can get to the point where you're investable and ready for growth?
Rei Wang: Yeah, there's a lot of different avenues these days. And again, you made a great point earlier around people come from different networks and have different access to.
So a lot of people, if they come from a strong alumni network, whether it's a previous employee. lawyer or university, you know, they're able to almost create a small angel round by just asking friends and family and alums from those [00:32:00] networks, if they're willing to make a small investment, right? So that's what we call a friends and family round.
You can say, I'm trying to raise a hundred K here. And if you can get a hundred people to put in a thousand dollars or maybe 50 people to put in 2K. Like that can spin up really quickly too. There's also platforms out here that can help with this too. I personally haven't raised on any of these platforms, so I can't speak to them in detail, but I'm sure you can learn more by checking out AngelList or Republic.
There's lots of different ways for people to start these rounds with many investors writing small checks to help in a friends and family room. Yeah. So I think a lot of these tools will actually will help you do that now. And usually they'll help you kind of create a syndicate. And then I think even Carta might have this new functionality now where they'll almost create the cap table for you.
There's also a company that used to be called PartyRound that just rebranded. Think their new name is Capital, [00:33:00] but they do this specifically and will help manage all of the documents and equity.
Amy: Well, my admiration goes to all the startups. Struggling out there to build something amazing and make it happen, but even in a difficult market, and I know you're among them and I really appreciate your taking the time here.
I've got a bunch more questions, but I do want to give you an opportunity, Rei, to let us know if there's anything coming up. or happening over the next few months that you're excited about that you'd like to share with us.
Rei Wang: Sure. Thank you for that opportunity. I think for us, we are really now thinking more about how do we work with teams and companies to help coach and support every single employee to become the most resilient leader possible.
So for everyone out there who's listening, if you. If you are a company leader or operator and you'd like to partner with the grant, please definitely reach out. We've built [00:34:00] a lot of cool new product offerings and features specifically for teams on the B2B side. And I would love to take you through them and give you a demo of what's possible.
Amy: Very exciting. All right. so much for your time. I really appreciate it. I know I learned a lot. I'm sure everyone else did.
Rei Wang: Thank you for having me.
Amy: I'll talk to you soon, Rei.
Rei Wang: Have a great day. All right. Take care everybody.
Outro: Thanks for listening to Getting2Alpha with Amy Jo Kim. The shows that help you innovate faster and smarter.
Be sure to check out our website, getting2alpha.com. That's getting2alpha.com for more great resources and podcast episodes.