Anita Hossain: Empathetic Coaching, Thriving Communities & Navigating Career Transitions - E125

Anita Hossain is Co-founder and CEO of The Grand, a learning and development platform to help people navigate transitions at the intersection of work and life through the support of group coaching and community. Anita has extensive experience as an executive coach and group facilitator, supporting clients on their journeys to become the most effective and intentional leaders they can be.

She previously was The Head of Knowledge at First Round, where she designed and launched hundreds of learning initiatives – from summits to unconferences to masterclasses and more – providing entrepreneurs and tech operators resources to stay motivated, accelerate their businesses and build community. Before joining First Round, Anita was an Assistant Vice President at Deutsche Bank and managed over $400MM in investment portfolios for Latin American clients. She also worked for MTV and Nickelodeon to create integrated marketing strategies and amplify their social impact initiatives.

Anita graduated magna cum laude from Georgetown University, where she studied Marketing and International Business with a minor in Spanish. She is also an MBA graduate from The Wharton School of the University of Pennsylvania.

Jeremy Au: (00:30)

Hey, Anita, welcome to the show.

Anita Hossain: (00:31)

Thanks, Jeremy, excited to be here.

Jeremy Au: (00:34)

I’m so excited to share your journey because you’ve not only, obviously, been a great hit of knowledge at First Round Capital that’s the start of your tech journey. Also, you’ve been a great coach that I’ve personally known as an individual coach as well as a founder of a coaching community as well called The Grand and so it’s been interesting to see you transition from VC to coach to founder and coach, I guess. So, yeah, excited to see and explore that. 

Anita Hossain: (01:07)

Yeah, and you’ve kind of seen me through all those transitions, so I’m excited to chat with you more about it today. 

Jeremy Au: (01:12)

Yeah, so, for those who don’t know you yet, how would you introduce yourself professionally? 

Anita Hossain: (01:17)

Yeah, so, I would say that the two main pillars of my life, the things that you need to know about me, is that storytelling and community are a big part of who I am. When I think back to my personal and professional experiences, it started when I was a kid growing up in Wisconsin, my family is from Bangladesh and the way that they really cultivated the sense of community is - we would travel around the country performing Bengali plays and it was a way for us to tell our stories but also connect with a group of people, other Bangladeshis in America and create a sense of community when my parents were so far from home and so I think that really instilled something in me and I carried that throughout not only my personal life but also my professional life. After college, I worked in finance and I noticed that women, VP level and below, were leaving at a higher rate than their counterparts and so I created a community for them to share their learnings, just understand the senior managers across the firm and this created a lot of career mobility. After that, I decided to take a leap and pursue acting for a little bit which we could talk about later and then I went to Business School. While I was at Business School, I created a platform called Storytellers which allowed people to get out of what I call real time talk and so I don’t know if you experienced this at Business School, but you know 800 people per class. Everyone would just go to the default of how was that test yesterday? How was that party last night? What are you doing this weekend? 

I wanted to create a platform that really helped people get out of that small talk and share who they are, what they value and really get to know each other. This started as something small and it grew to become the largest organization on campus. Today, the Dean actually talks about it as one of the reasons you should go to Wharton; that was really cool. 

Then I was at a crossroads and I almost moved back to New York because it’s one of my favorite cities, but I decided I’ve never lived in California before and so I booked one ticket, I packed one suitcase, and I just showed up, and decided I would find my next thing there. That’s when I found the role at First Join Capital as the head of knowledge…yeah, it’s such a Silicon Valley title, but I loved it and what it meant was - I worked with all of our portfolio companies really helped understood what challenges they were facing and I would design learning experiences so that they can share knowledge with each other. Through that work, I actually met my co-founder Ray and I’ll tell you more about how we started The Grand specifically, but I also became an executive coach through Reboot and so I was working one on one with a lot of individual entrepreneurs and founders. 

While at first round I was organizing peer groups of founders so that they can learn from each other and what I notice there is that everyone went in with this feeling of I need to share how things are going well, I’m crushing it, things are awesome, and I really wanted to push them to share what was hard, what is their self-identity/self-worth, and are they feeling like they’re good enough in that role? 

That’s when things transformed and people would stay for four or five hours really talking through all of these topics. I saw the magic and the power of this and Ray and I decided, what would it look like for us to build a platform where it’s not just for founders and entrepreneurs, it’s for people of all different ages, all different geographies, backgrounds, industries, where they can come together and get that level of peer support when they need it most. So that’s really how the Grand was born and our thesis around when people need it most is when you’re going through transition and you feel like you don’t have anyone to talk to. 

So, that’s a little bit about my journey and how I started The Grand and became a founder today.

Jeremy Au: (05:33)

Yeah, what a journey. Talking about transitions here, you’ve made quite a few in your career. I gotta ask, how did you make that transition into the technology world because you had experience, obviously, in the banking world which is very straightforward and you did a solid six years there so you could have kept going, kept climbing, to that assistant VP level and it’s a nice job, especially in New York. So, how did that transition happen? 

Anita Hossain: (05:58)

Yeah, so, I was feeling like it was time to make a transition when I noticed within myself two things. One, I wasn’t able to be as creative as I wanted to be day today and, two, I couldn’t really see the impact that I was making. Obviously, I stayed there for a long time and the reason I did is because I had those things in the beginning. I somehow finagled my way into a Latin American team doing business in Spanish. I was the only non-native Spanish speaker. It was really hard. I majored in Spanish in college and it was still very challenging. I stayed there for a while, but after I lost that impact and that creativity, I decided it’s time for a change. Naturally, I went to Business School as some people do.

For me, what I’ve found is that I really, really wanted to work in something where I can marry my interest in storytelling and social impact, and these are two things that there are a lot of roles that could fulfil that, and there’s no straightforward path. What I did was I used business school as a way to explore those things that I was interested in, and I called that theme of my life “following my curiosity”, and that’s kind of what I’ve done throughout. 

So, when I moved to California, I ended up deciding that, OK, I wasn’t necessarily looking at venture, and I wasn’t looking at start-ups, but when I read the job description, I said OK, they’re describing me right now and what I loved about it was that it was extremely entrepreneurial. It was really creative and I worked with some of the smartest, kindest people that I’ve ever met. I think with all of that, I just took a leap of faith. They took a leap of faith on me and I think it definitely married my interests because, at the end of the day, I helped our founders with self-discovery, I helped them become more resilient in their roles, and I helped just create a more open and vulnerable ecosystem, which is what we need in venture and in start-ups. 

Jeremy Au: (08:20)

Amazing. You said this interesting phrase that you took the time at business schools to explore yourself so you know there’s a lot of people who are thinking about using business school as a way to get a sabbatical or to do a transition. What do you think about that? Should people just save themselves a quarter of a million bucks and use that to spend it on a retreat or something. Which situations do you think makes more sense versus those that make less sense? 

Anita Hossain: (08:48)

Yeah, my thought there is you should only go to business school if you know exactly what you’re going to use that platform for. I don’t mean you need to know exactly - I’m coming from finance and I want to be a consultant. You don’t have to know that for sure, but you need to be very clear on how you’re going to use the experience. What I mean by that is when you go to business school, it is overwhelming because there’s so many things that you can get involved in and what happens is when everyone else is lining up for a particular door, you also line up for that door because they’re like, oh, everyone else is lining up for it. 

If the door is consulting or finance or whatever, you line up for it because it’s easy to get swept up into it. If you don’t have a clear sense of what it is that I want, what I want to focus on, it’s easy to get caught up in it, and so, for me, what I was focused on was building out my leadership skills and so everything that I did was really how I can develop on that. So, I started that storytellers organization that I talked about, I worked on a nonprofit that we founded, everything was really set up for that. I wanted to develop strong relationships with my classmates, our professors, and just building out that community was really important to me and I wanted to use that time for self-discovery to know what really makes me happy, how I can live a more meaningful and more purposeful life. That lens helped me say no to certain things, and yes to certain things, and so my advice for folks would be - if you’re really clear about what it is that you want, and you can use business school as a means to get there, great. But, I think if you’re using it as a break, it’s a very expensive break and I think there are other ways, it doesn’t have to be business school, there are other ways that you can get that level of clarity and support. 

Jeremy Au: (10:53)

Yeah, that totally rhymes with what I think too. I think it’s a very expensive way to take a break, but it’s a very good way if you know where you’re trying to get to, right? How did that transition to technology take place then venture capital? 

Anita Hossain: (11:07)

Yeah, so, again, I found out about the role and I was able to really position myself as someone who’s built community; I’ve built things from nothing. I’m the type of person who loves to create, loves to experiment, and so from that, the background that I have in just all of the things that I’ve created in my past career, within finance. Those organizations that I talked about within Business School, that entrepreneurial spirit allowed me to really dive in head first into venture. Frankly, I had to get up to speed though it was a little daunting at first, I definitely had my own bouts of impostor syndrome going in. One of the first experiences that I designed was a conversation among CTOs at early stage companies and, Jeremy, I was so nervous. I was like how am I gonna lead a discussion with a group of CTOs. I realized that I needed to guide them. I needed to create and design that safe container where they can share and be their authentic selves so that they can emerge more resilient in their own roles, and that’s what my superpower was. I know how to create safe spaces. I know how to get people to share openly. I know how to build community in a very compelling way, and so that allowed me to get over this hump of - I haven’t been immersed in technology for 10 years before I joined. 

Then I would say the other thing is, at the same time, my co-founder. She also started and didn’t necessarily have a deep tech background and we started about a month apart from each other and so Ray and I really bonded over this. Once we’re able to share that openly with each other, we also shared with some of our colleagues and we designed our own peer support group within the firm of women who worked at First Round and that really helped us become more confident in our roles. 

Jeremy Au: (13:12)

So, you’re casting itself as someone who was an unconventional pick, right? You didn’t feel qualified for that role and it was a new role too. Why did First Round Capital say why Anita, what were they looking for from your perspective? 

Anita Hossain: (13:28)

I wouldn’t say I wasn’t qualified for the role. I would say I didn’t have the traditional background in terms of what I thought they wanted. When you think about a venture firm and you look at everyone’s path, everyone comes from such a unique place. It’s not like a straightforward engineer or marketer that you could see the steps and it makes sense that they’re in that position, so I would say that, for me, what they saw in me…I mean, we can go ask them and get clarity on this, but again, the way I think about First Round is that it’s a venture firm that acts like a startup so you need to be very scrappy. You need to experiment. You need to be really creative. I’ve proven all of those things, and I think that’s what they were looking for. When you think about breaking into an industry that you don’t have experience in, I think, a lot of times, they do hire for potential and if you can really show what you’re capable of, then the rest is history, so that’s what they saw in me. 

Jeremy Au: (14:38)

Yeah, and you know, it’s interesting because you have this duality or this bridge role, right? The VC is very much - we’re here to invest in companies that will become unicorns and we hope to support the rest as well in that journey, so we’re looking for that net return at the end of the day. Obviously, founders are there saying here’s the capital, I’m going to grow as fast as I can to go from point A to point B to point Z within five years or somewhere in between because you’re not making an investment decision on that, and you’re not on the operator side, you’re holding that space in between. Could you tell us a little bit more about what were the opportunities or that duality or bridge and also what were some of the shadow side of that role?

Anita Hossain: (15:23)

Yeah, I would say that opportunity is that I was able to work cross functionally with every single person at the firm and so I was really able to understand what they were interested in, how they wanted to support their companies, and I brought that to life. When I think about the contributions I made, so I thought about my role in three ways. It was, one, to help build our brand. Two, to really support our companies as much as I could, and, three, to find new investment opportunities. So, I did have a hand in all three. I think that what really helped my role in similar roles out there stand apart is that capital is a commodity. You can get money from any firm, but what really sets you apart is how you support each of your founders and, as a founder yourself, you know how challenging that journey is and so I think that the upside was I was able to build trust with everyone, every founder that I worked with, and really meet them where they’re at so that they could do their jobs even better and feel that level of support.

I think when you think about firms who are investing in their companies in that way. Like our investor and the Grand 776, they really, really support their founders in a compelling way. First Round does that as well, like so many different firms have seen that this is how we’re going to stand apart. I would say that is the positive side of being in this dual role.

Jeremy Au: (16:57)

What would you say are some of the shadows or tensions of that role?

Anita Hossain: (17:01)

I think the tension is there's no clear road map, so you define the scope and so frankly, if I had done the same job that I did the first year, I would probably get bored and I wouldn't succeed, but it was up to me to continue to grow the scope of what I was doing and, again, think really creatively and have a pulse of the community and build with our community to help serve their needs. So, things like our staples at First Round today, things like their angel track program, founder forum, those are the things that I was able to really focus on; how do we create a more cohort-based support for our community? That, to me, was really interesting because I was able to constantly learn, understand what our companies needed, and how we can help up-level them with the platform support that we provided. 

Jeremy Au: (17:57)

So, there you are, you’re helping out these founders through everything you’re creating the role for yourself, adapting it, building up because nobody has really built out this kind of role in the VC world, and helping these founders through their transitions and, there you are, you start becoming an executive coach with reboot which was how I got to know you. How did you make this decision to be like I’m no longer in finance, I’m in VC and I want to coach. So how did that happen? 

Anita Hossain: (18:26)

The spark that helped that happen was – One, I was coaching without really knowing that I was coaching, so that is how I was serving a lot of our companies. Two, I met Khalid Haleem, one of the cofounders of Reboot because we hosted a session together with some of our portfolio founders on what to look for in a CEO coach, how to structure your sessions for success, and few other topics, and I was really blown away by him because he was rooted in data, science, and psychology, but he also brought this empathetic side, this human side. I was just wowed and so were all the founders, at his approach. We connected, kept in touch, and I asked him more about his journey. 

Going back to stories, it’s really helpful to share stories because not only can you make meaning of your own experiences through stories, but you can make real connections with other folks and see yourself in their stories as well. So, he was able to share his journey and I asked him if I wanted to be a coach one day, what would that look like and what he would recommend. He said that I had a really good vantage point because I was working with all these companies already. The best way to do it is to really start and I ended up taking a course in Neurolinguistic programming, which you recommended, and then thereafter I joined as an executive coach with the team working both at Reboot and First Round, frankly, because both jobs made me better at the other and it was incredible to have that opportunity. 

Jeremy Au: (20:11)

What’s the difference between being a coach versus being a VC kind of support role? What things did you have to change about how you practiced or were present while being with a founder? 

Anita Hossain: (20:24)

Yeah, I do think that the best VC’s are coaches and I will say there is a time and place for that. When I think about the difference, it’s sometimes, your companies are coming to you and they need guidance and support in the sense of hey, everything’s burning, everything is on fire, what has another company done in this situation, or what do you advise me, because you’ve been there before. That definitely has a time and place. I think the difference with coaching is when you’re really supporting people, you’re not doing it to fix or solve their problem. You’re actually doing it to help them reveal their inner teacher and we do this with empathetic listening, with asking open and honest questions so that ultimately, they can understand what is the best path forward for them. 

I think that as any type-A leader, it is really hard to shift gears and we always have this sense that we need to provide the solution, we need to be the person who fixes and solves. It’s really hard to shift that mindset, but when you do, that’s when you can create profound change and I’ll add to one quote that we often quote both at Reboot and at The Grand is that the human soul doesn’t want to be advised, fixed, or saved. It simply wants to be witnessed, to be seen, acknowledged, exactly as it is, that’s from Parker Palmer. I think that just really sums it up. 

Jeremy Au: (22:02)

So, Reboot is an interesting space because it’s one of the few, I would say, coaching agencies or organizations that, obviously, at one level, is tackling the technology and startup space, especially for founders, but also as one of the few places where coaches are not total freelancers, but also acting as a coalition. Tell us more about what made Reboot special from your perspective.

Anita Hossain: (22:26)

What made it really special is that we focused a lot on radical self-inquiry which I just mentioned with asking open and honest questions. We focus on practical skills because at the end of the day, that is what folks need to get to that next level, and then we did acknowledge that peer support is really powerful, and so I think that those three in combination is what made Reboot so thoughtful in their approach and, like you said, because it was a collective or coalition, we all learned from one another too. So, it wasn’t like this independent ok, I’m just going to go off and do my own thing. We had the flexibility and freedom, but we also learned in community with other coaches and, that, I think really helped us all level up and become better at our craft because, again, whenever you start something new, it’s scary like that’s the whole premise of why we started The Grand. It’s lonely, it’s scary, you might not feel good enough. There’s a lot of negative self-talk associated with it and so to be in a place where you feel truly supported and you can be with other people who are in that similar transition, becoming coaches too. I think that’s what really set it apart. 

Jeremy Au: (23:47)

And here you are, you’re coaching everybody, all these founders, you’re working with founders at First Round Capital as well…somewhere along the way, you’re starting to talk to Ray, who is awesome, and you’re starting to think and have the founder itch yourself. So, what was that like? 

Anita Hossain: (24:03)

Yes, so it kind of painted the picture of the work I was doing with founders at First Round and I painted the picture of the one-on-one work I did at Reboot and what we noticed is that all of this is for founders and entrepreneurs and the executive coaching is one on one and it’s only for executives. It’s only for people you know at the top and it’s really cost prohibitive for everyone to get access to it. That got us thinking that it would be really, really powerful for us to support everyone within an organization because that’s truly who needs support to be able to be the better version of themselves and they’re the ones who become the executives, ultimately. So, we really connected over that and also the fact that, at this point, loneliness is the greatest health epidemic of our lifetime. That was the backdrop of when we started thinking about building something together. As we dug into the research some more, we realized that most Americans don’t have a single confidant. That means they don’t have a single person to talk to about their dreams, their hopes, their fears, and that really struck us. We kept coming back to these two things; we saw the power of our work, we saw this big problem and ultimately decided that we are the best suited to go out and solve this so let’s do it. 

Jeremy Au: (25:35)

It’s interesting because you started doing that and how did you start building it? What was your first MVP…how did you find out that people wanted that version of the coaching program or approach? 

Anita Hossain: (25:49)

Yeah, so the way we started is we simply put up a Google sheet on Twitter and it said “What’s keeping you up at night. If you can get guidance on anything, what topic would it be?” We put it up and we were both watching people fill in responses and it was incredible to see, again, how honest and raw people were about what was keeping them up. From that list, we stat-ranked it and decided to start our first product, which was called sessions. We brought people together around various topics like should I have kids or not, or how do I find the right life partner, how do I make a big career transition, how do I deepen my relationship with my parents, all these like really deep human topics and we would gather a group of 10 to 12 folks in people’s living rooms, it was all in person. We’ve gathered 400 people at that point and it was really, really incredible, really powerful. People who would have otherwise never met each other. After we saw this model working for some time, we realized, one, people wanted to get to meet each other more than once and they wanted to build deeper connections with their groups and, two, they really wanted to go deeper on the topics themselves. It’s really hard to cover making a career transition in a 2-hour session and feel really satisfied. It’s almost like we were just scratching the surface and so from that we realized, ok, what is the next iteration of The Grand? What’s that going to look like? That’s when we introduced our flagship product, The Quest. The way The Quest was designed was we brought together a group of 8 to 10 people, like yourself, meeting with their group every other week for two hours and you go on this narrative arc, this journey together with the curriculum that we designed. What makes it powerful, is that there’s a lot of reflection, a lot of self-discovery and you’re also able to do that for your peers. When we say things out loud, we might not be able to connect the dots, but someone in your group, let’s say, Jeremy, you’re sitting there and you’re like, oh, how I would connect it for you, those are the a-ha moments that people had. 

That’s how we started in February 2020 and we launched one in San Francisco, in person, and another group, remote, and thank goodness we did because we, obviously with the pandemic, had to move everything online. At first, it was really scary. I can share a little bit more about that, but in the end, it was really beneficial to us because we were able to serve a global community. People from all over the world participated in The Grand. To date, we have 20 different countries, six different continents and it made us realize that our topics are universal and when you bring people from different countries to talk about it, it adds this other level and layer of richness to the conversation. 

Jeremy Au: (28:59)

Yeah, I remember being one of those first customers of The Quest and I really enjoyed that online digital approach which, like you said, turn out to be serendipitously helpful. Obviously, much more accessible to everybody in the group and I had an absolute blast, so definitely recommend to anybody is listening to check out The Grand. What’s interesting, along the way, of course, is that you built it in a different way, because obviously for most coaching people they’re working as Freelancer so obviously working on cash flow even reboot very much, is something that’s been very much an agency approach. For yourself, what’s interesting is that you’ve also decided to kind of wrap it up and take on capital from Alexis Ohanian so and I always remember him because I used to watch his YouTube show Small Empires quite a lot, but it’s interesting, right? Because you’re choosing to take on this C capital, right? So, you’re also moving beyond not just being a founder of a coaching agency, but also pushing towards more of a startup approach. Talk us through a little bit more about that - Different approach to the coaching growth, trajectory and capital growth requirements. 

Anita Hossain: (30:08)

Yeah, so we wanted to build something that was meaningful and that created real change and we didn’t want to take on money at first until we proved that out. For us, it was really important to build with our community instead of building something, presenting it and saying do people actually want this? I think, especially because our focus is on group coaching, it’s on peer support and community, that was the right approach for us. Once we developed The Grand Quest and we’re able to hone in on what it is that our product is and we were able to get an NPS of 90, people were referring their friends and became really strong advocates for us. That’s when we knew, ok, we’re onto something. This can help so many more people. What is the best way that we can actually scale our impact? 

It was me and Ray, a team of two doing everything. The best way that we can actually scale our impact is to hire a bigger team and really serve more people with The Grand. That’s why we came to the decision that the best way we can do that is to raise capital. At the same time, traditionally, most people have come to The Grand as individuals. Some other folks found us just through their own journeys of wanting to get that support when they were in transition. Ultimately, what we want to do is we actually want to also help employers support their teams when they’re at these pivotal role changes or milestones in their careers and their personal lives. Our belief is that if we have companies that invest and care about their people, and not just for their work experience, but their human experience, then we can all benefit from that and become more resilient, have a deeper sense of belonging, connection and all of that leads to higher performance and greater outcomes in the workplace. Now, at The Grand, we are partnering with companies that care deeply about their people to really bring them to The Grand and partner with them.

Jeremy Au: (32:18)

Yeah, so using the capital to expand, go B to B, but also to scale that impact. What’s the difference now that you’ve gone through it? Because before this you were supporting founders and after that you are coaching them, and now you are one so there must be quite…changing the sides of the table right? Were there any things that you didn’t really realize you know, while you’re supporting everything but now you’re a founder, you have a different eye on it, or a different appreciation of? 

Anita Hossain: (32:50)

Yeah, I would say that being close to it, working in venture and being an executive coach, I felt like I knew the reality of what it was to be a founder. The ups and the downs and I knew that there were moments of “Oh my God, we’re onto something great. This is going to be huge.” And moments of “Oh my God, this is not gonna work. What are we thinking? This is awful”.

 I just didn’t know that the rate of frequency. What I mean by that is, that can happen in 15-minute increments several times a day. I think that’s what really has surprised me about the journey and something that you don’t actually know it until you’re in it and then you can feel the impact of it. The biggest challenge of now being in the founder role is that emotional regulation of just knowing that what you’re doing is worthy of your time and you are worthy of it, and just keeping on going because I think that is the challenging part. When I think about what's helped me there is just awareness of that. One of the greatest gifts I got from my previous roles is that I was at the table with early-stage founders and growth stage founders, ones who've made it, you know, you'd hear their names and you’d know they’ve made it. I realized that they are also figuring it out and learning as they’re going along, and they don’t have it all figured out yet, and that was the greatest gift. Knowing that everyone is doing the best that they can and they, too, might have bouts of impostor syndrome. So, I think going in eyes wide open was really helpful and just reminding myself not to compare my background or my behind the scenes to their highlight reels. Does that resonate with you?  

Jeremy Au: (34:43)

Oh yeah, it totally resonates with me as well and I think it's nice because he summarized it. Which is – it is the nature of the thoughts which is emotional regulation but also the frequency of it because of the fact is a new business situation, a new meeting, a new thing you haven't done before, so the frequency or, I could say, the triggers of it come out multiple times? Let’s talk a little bit about because a lot of people don’t really know what the emotional regulation actually is, or what the flavor of that thought is, and you’ve seen it across hundreds of hours, and using it yourself. So for those who don’t really know that yet because they’re not yet a founder, maybe already a founder, or outside looking in. What is the flavor of that emotional regulation?

Anita Hossain: (35:26)

I think it starts with the stories that we tell ourselves, and so we might engage in this negative self-talk like we’re not good enough or who am I to be a founder of this or what have you? I think it’s really just stopping that negative talk or that limiting belief and being able to reframe it and that’s something that I’ve worked on personally, but also something that I’ve helped other people do and a lot of it is bringing some of what’s subconscious into consciousness, and then you’re able to actually go ahead and reframe that thought. That’s an exercise in terms of emotional regulation that I definitely recommend folks to do and then the other thing is, talking to another founder about this the other day, that sometimes, noticing the fear is actually a good thing because it lets us know that we’re working on something that is big enough, it is worthy of our time if we went day today and never felt any level of fear or doubt, then maybe we’re not working on things that are actually truly worth our time. 

Jeremy Au: (36:39)

What’s the downside of just suppressing it, it is go rolling with it right? Because I think that’s a big one, right? It’s like just tough it out. Everybody has it just crush it or crushing it. Just tell yourself you’re crushing it. Tell each other that you’re crushing it obviously don’t say it out loud, but that’s very much the flavor of what doesn’t kill you makes you stronger. What’s the downside of that? I think the upside for me is like it feels good and it’s easy to say, at least, but how would you say some of the ways it could play out negatively?

Anita Hossain: (37:14)

Yeah, I mean, I actually don’t believe in the fake it till you make it where we’re crushing it just everyone just pat each other on the back. I actually think it’s the opposite that is powerful which is sharing and practicing vulnerability. One example is when I was working with founders. I run this. Empathy exercise where I have them share things that are keeping them up at night. The biggest challenge that’s on their plate and I anonymize it so that everybody else can read someone else’s. I have people raise their hand if what the person wrote could basically have been what they would have brought to the group. Things like I feel like I’m everybody’s cheerleader but no one is mine or I feel like I’ve been working on this company for so long, but we’re just not getting it. You know, it’s been seven years or like all of these examples and I actually think saying that out loud is what’s more powerful because we’re able to acknowledge it and confront it and then know that we are not alone in those feelings and only then can we move forward and keep going. So, I think that it’s not just the cheerleading, it’s also the challenge. It’s also the being able to confront it for ourselves and for each other. And I think one thing that comes up for me is when I think about Ray Dalio principles, there’s this image of the squiggles I don’t know if you’ve seen that or read the book, but what’s helpful about that is he talks about having audacious goals and then you might fail, but then you learn from that failure and that allows you to have even bigger, more audacious goals. As long as that squiggle or that spiral is on an upward trajectory, then you’re in good shape because you’re constantly learning, and so if that’s the case, those failures are just points where you can actually get better in the long run.

Jeremy Au: (39:19)

But vulnerability is scary, right? Let’s talk about vulnerability. Let’s talk about empathy. It’s scary, right? Nobody wants to say they’re vulnerable. I can’t imagine a founder going up to VC and saying, hey, I’d like to share my vulnerabilities with you. So, what do you have to say about that? Like that fear you and I can talk about that word because we’re comfortable with that, but it could also fall so flat in so many arenas of that conversation. So how should founders think about vulnerability and the spaces for which that can come out?

Anita Hossain: (39:53)

As a leader, it’s important to be and to model that vulnerability because it allows your team to show up in a very authentic and real way and what I mean by that is when you give people, I like to think of it as a, “social permissioning”. At a baseline, we don’t go there because we feel like, as humans, we don’t have permission to go there. If I had just met you, Jeremy, we would probably talk about the lowest common denominator. Things like the weather, where we’re from, what we do for work. But if you create a space where you allow people to actually go deeper, that’s when they feel comfortable sharing, and I believe that people do want to go there, they’re just not given permission in a day-to-day space. Once you’re able to make it safe for people, and I do think that comes from the top, then I think people are able to really rise to the occasion. The reason it is so important is because now, more so than ever, you see what happened with the pandemic and the state that we’re in today. We need to acknowledge everyone’s human experience. It can no longer just be - we have our work self and we have our individual selves…our personal selves. I don’t mean that we need to share all parts of ourselves always, but we need to feel comfortable that there’s psychological safety that there’s no negative repercussions for really being our authentic selves and saying and sharing how we truly, truly feel. It’s hard, I will acknowledge that it’s hard. I don’t think that these things change overnight, but as leaders, as empathetic leaders, I definitely think it’s important to practice that and it’s a way for you to, again, build deeper connections across the firm with your teams.

Jeremy Au: (41:51)

Yeah, that authentic connection comes from sharing the dark times and the tough times about who and why you are, so I’m curious about for yourself here. Have there been moments where it’s been dark or tough and that you had to choose to be brave?

Anita Hossain: (42:07)

Yes, absolutely. I would say this period of my life is a pretty brave one and the reason is because I’m doing two jobs that I’ve never done before - being a founder and CEO, and being a new mom. I would like to sum it up with a visual. I was six months pregnant, decided in the middle of the pandemic that we wanted to be closer to our families, and so I bought a house online. I decided to, you know, never seen it, decided to road trip to Wisconsin back where I grew up with my husband, was six months pregnant, was fund raising. At the time, we ended up getting a flat tire in this road trip and then you know our tire broke and so, long story short, I was in the back of a tow truck driving to Minneapolis, on investor calls, bumping along, 6 months pregnant. 

When I think about being brave, it’s just putting myself out there in situations where there’s just a lot of uncertainty and just taking the plunge and that’s one experience that comes to mind. There are a few others, but I think that’s the one that just struck me and that is close to my heart right now. And fun fact, my daughter’s name is Zaella and it actually means brave, and so I hope that she takes some of that bravery and goes forth and dives in head first into whatever she wants in her life. 

Jeremy Au: (43:49)

That’s amazing. It’s so sweet and also crazy story as well. So many emotions. And that’s a crazy visual right, because that is a challenge for so many founders around whether you can be a founder, can be a parent, right? And it takes, it takes different flavors, right? So, it ranges from I’m a founder now, and I don’t know whether I can have or should have kids because I’m so busy as a founder. Yeah, and there’s a tradeoff between being a founder and having a kid or anything, just always at the end of the scale would just I want to be a founder, but I also want to have kids and I want to have kids first and then be a founder leader. Or if I be a founder I’ll have kids later, right? And, personally, for myself. you know I had the same situation where I was weighing different offers to found something of my own. There was startup opportunities for me to come as a COO or turn around the business and things like that. And there was a VC role so that I eventually took up. Out of that, I was also aware that in this case we had a baby on the way as well. And so that influenced how I was making a decision. So how do you think about that trade off on your end, like what advice would you give to people who are weighing the founder life and having children?

Anita Hossain: (45:06)

Oh, that’s a heavy one. That’s a hard one and I would say that the thing that helped me is just being flexible and enjoying the journey. It is so hard, I think being a founder is, again, really hard because what we talked about before, there’s so many new things that you just have never done before and, at the same time, being a parent is the same thing times two because you’re not sleeping and you know there’s so many other things that are happening. And so. If you get caught up in this, again, self-talk of am I good enough or am I going to be good enough? Then you might limit yourself, but the best advice I can give is if you allow yourself to enjoy the journey to be really flexible and to really ask yourself. What it is that you want, then, I think you can go for it and know that it’s all worth it and I don’t think that makes it any easier, but it helps you become really clear in what you’re doing at all for and if that is really what you want.

Jeremy Au: (46:21)

I’m curious because you made a decision to keep going ‘cause you know, obviously, based on chronology, you were already a founder. Yeah, and around there and then along the way you decided to continue having a family, that trajectory. I’m just kind of curious about that chronology while you’re in that pickup truck/tow truck, bouncing around, obviously, so I think you had one visualization at a time about what your life would be once the kid arrives, right? I’m just wondering if there’s any difference between your then conceptualization or visualization of your actual life as a new parent and a founder versus what the actual reality of that is. Would love to hear if that changed or evolved as well.

Anita Hossain: (47:03)

Yeah, I mean, I think you can anticipate it, you can rationalize it in your head, you can read all the books, you can talk to all the people about becoming a parent, you really don’t understand what it’s like until you’re in the thick of it because it is such a challenging emotional…like physically challenging experience as well. But at the same time, my heart is so full and as cheesy as that sounds something as simple as, oh, she smiled at me. You know, it’s as simple as that. Keeps you going and, in fact, one thing that struck me about the whole experience is that it actually helps me think about my purpose and my meaning and what I want to do and how I want to contribute to the world and if I’m spending time away from her, I want to be doing that intentionally, working on something that I believe in and really living out my purpose. So, The Grand and working on something that we put so much heart into, something that impacts so many people’s lives. I can’t imagine working on a better thing while being a mom as well, and so for folks out there who are contemplating - is this right for me? I think if you are really working on something that you feel really strongly and deeply connected to, it will make it all worth it and you won’t feel bad about having and doing both because you’ll derive different sense of meaning and purpose from being a founder and being a parent. I’m curious, I want to throw the question back at you. How does it feel being a dad; happy Father’s Day, by the way, I know you’re celebrating today, so how does it feel now? What is the reality like for you? 

Jeremy Au: (48:56)

Similar to you, and I obviously don’t over work and research and I also had an added benefit of having my second startup be one in early education. And so I got always like joke is somebody say like along the way. I also invested millions of dollars of investor capital to learn what being a dad would be like by working with thousands of parents, right? And so I got to see so many different  family journeys. And I think it was a tremendous responsibility, but also joy to really help so many families, at that high level with their families and making things easy and better. It was still a little bit high level, you know, so what I mean by that is when you have your own kid then, maybe it’s similar to being a VC; supporting founders to being a founder yourself. It’s still high level because when you have the kid then you’re like I don’t just love all kids as a group and I also love this group of kids as a volunteer and as a teammate and a steward, but I also love this kid, one kid so much. I think always, in the back of my head I always had a perspective of like tradeoffs, right? ‘cause you know when you do one thing you do another thing, but I think one thing I’ve kind of forgot along the way is like how much more of, not just a joy, but also a love. Yeah, you know, a parent will do anything for their kid. That also includes doing your job better. So, there’s all these artificial tradeoffs we look at. It like, do you love your work or do you love your kid? You know so reductionist which is that when you love your kid, it lets you love your job, if you had a good job, more because it lets you put together the family and the structure, and the time for you to love your kid. There’s a bit of a flywheel that it’s not a zero-sum game for love, right? I thought was nice to have a big baby version reminder every day of that love.

Anita Hossain: (50:41)

Aww, I loved that. Thanks for sharing that.

Jeremy Au: (50:44)

Well, one last question I have is if you could time travel like 10 years back in time back to when you were still in banking right? And so in 2011. What advice would you give yourself back then? If you just popped out that time travel capsule. 

Anita Hossain: (51:01)

Yeah, let me think about this one. That’s a good question. The advice I would give myself is that the risk of not doing something is greater than doing it and failing. I say that because I was working in finance for a long time and I had again some ideas of other things that I could potentially do, but, I didn’t take the plunge and there are always times that you could talk yourself out of it because it’s too risky, you might not be good enough, all the things we talked about, and so if I could go back and tell my younger self that it’s worth the risk because, looking back, you always are going to think - Oh man, I’m too late, I’m too late. I should have done it sooner, I should have done it sooner. That can be really paralyzing, and so there’s no better time than now to dive right in whatever it is that you’re contemplating. 

Jeremy Au: (52:02)

That’s really sweet and really thoughtful. Thank you so much, Anita. I’d love take this time, just to kinda like paraphrase the three big themes that emerged for me and that I took away from this conversation. 

I think the first, of course, I just love the phrase you used – transitions? Because you used that phrase to describe your own career transitions from finance to business school to acting. I guess we’ll save that for another time. To being a VC to being a coach to being founder yourself, and so it’s interesting because I think it’s a nice way to think about them, not as departures but this transition about different chapters you mentioned. It’s also interesting because your own founder journey and startup that you’re doing now is about helping other people with their life and work transitions as well, and so, I think it’s a very nice poetic loop where you’re helping others where I’m sure others have helped you before in those transitions as well that you mentioned.

The second thing that I really enjoy, of course, was obviously some of the industry nerding out over venture capital and the bridge/in between space between founders and VC’s and, I think, the benefits of seeing both sides, but also the tensions that can arise from there and some of the dynamics from do I have the space or credibility to speak about this issue or help facility that all the way to “hey what is going on?” And “let’s build this role from scratch and explore that”. So, I think there’s a good dynamic, but, overall, talking about seeing that and holding that space open for hundreds of founders on the VC side but also as a coach

I think the third thing I really appreciated actually was the humor I guess to me, at least, of you having worked with hundreds of founders and now you becoming a founder yourself is actually kind of multi comedic because here’s someone who has been coaching and holding a space for others and now you’re in it yourself and, like we shared, how difficult it actually is to be in a thick of it, not just from the flavor of the emotional regulation but also from the frequency from all the different ways you get triggered on it all the time. So, it’s this a really interesting dynamic around, and conversation, and openness about the actual vulnerability, the squiggles, the dynamics of being a new parent, in your case, for example, fund raising while with a flat tire, getting on the back of a truck while pregnant and running a startup, so, hopefully, that serves all as a space and guide for other people who are. Thinking about similar chapters in their life as well.

Anita Hossain: (54:40)

Thank you for having me. I loved having this conversation with you and thank you for being part of The Grand community and a good friend.

Jeremy Au: (54:48)

Thank you so much, Anita.