Grind Culture: The 24-7 “Work Day”

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Ep. #916 - Grind Culture: The 24/7 “Work Day”

In today’s final episode of Startup Hustle’s Mental Health Mondays series, we’re talking about grind culture. Our guest host, Jannae Gammage, is joined by a venture capitalist from Sixty8 Capital. Together with Nassir Criss, they open up the harsh reality of being in constant “work mode” and what it does to your mental health.

For those catching up, our Mental Health Mondays is a three-part series. Jannae and her guests have been exposing the truth about the mental health burden of entrepreneurship. They also share real stories that you can relate to and learn from.

Covered In This Episode

The grind culture among entrepreneurs has developed an unhealthy reputation. Being always “on and available” to become successful is not as beneficial as it sounds. What are the effects on your personal well-being as an entrepreneur?

Get Started with Full Scale

Take the time to sit down with Jannae and Nassir in this last episode of the Mental Health Monday series. They unveil how adopting a grind culture attitude truly impacts your mental wellbeing and the effects it has on your relationships. The duo also discussed their own mental health routines and how to prevent the pressures of being successful from getting into your head.

It’s time to prioritize your mental health over everything else. Listen to this Startup Hustle episode today.

Tips for Business Growth from Startup Hustle


  • Who is Nassir Criss? (01:41)
  • Nassir and his motivations as a venture capitalist (02:55)
  • How Sixty8 Capital helps underrepresented entrepreneurs and stakeholders (04:27)
  • The meaning of grind culture (06:34)
  • How different founders have different grind culture attitudes and routines (08:46)
  • Dissecting Nassir’s work routine (11:00)
  • On self-awareness, pushing limits, and burnout (15:06)
  • The entrepreneurial stigma of “keeping it together” (17:13)
  • Potential health and lifestyle risks of the grind culture (20:56)
  • The idea of “hustle porn” and how to counteract it with a holistic approach (26:03)
  • Looking into Nassir’s mental health routine (28:34)
  • On raising funding and preventing disruptive business growth (35:52)
  • What is LP? (39:24)
  • The symbiotic relationship of VCs, LPs, and business owners (39:59)

Key Quotes

To be able to know where your breaking points are, your weaknesses. Like how far you can actually push yourself and how to get the most productivity out of yourself . . . I think a lot of people don’t even get to that place where they like having that moment with themselves. They push until burnout and then try to recover from burnout. It is the most difficult thing to do when you are passionate about something. You want to continue to get yourself to work on it.

– Nassir Criss

Being able to say I’m going to change my environment because I’m back in hustle mode, startup mode, early-stage mode. And that’s really the only thing that I can control when it comes to my schedule and how my day goes. I started to focus on what makes me happy, and I was more productive. I was doing more revenue-generating things. It was just like a domino effect.

– Jannae Gammage

It’s essential for founders to do their due diligence to find investors that are aligned with the clauses and missions that they also want to serve. Yeah. Otherwise, you’ll be in a relationship that you can’t get out of. That’s a negative one.

– Nassir Criss

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Rough Transcript

Following is an auto-generated text transcript of this episode. Apologies for any errors!

Jannae Gammage 00:00
What’s up, everybody? We are back. This is your guest host, Jannae Gammage, coming with our final episode in this Mental Health Monday series. Today, we are talking about grind culture, burnout, and all the things. And I am going to introduce you to our first guest, one of my favorite people. But, first, I want to remind you that this episode and this entire series have been brought to you by Where you can build a software team quickly and affordably. So, today, I have with me Mr. Criss, VC at Sixty8 Capital, which is a firm dedicated to investing in underrepresented founders and innovators. Did I get that right?

Nassir Criss 00:48
Absolutely. Thank you for having me. I appreciate you.

Jannae Gammage 00:52
Welcome, welcome. So tell us who you are and why people should listen to what you have to say about this.

Nassir Criss 01:00
I don’t know if they should listen, but I would like them to. I think we both would like them to. Currently, a venture capitalist at Sixty8 Capital. We are, I should say, a Midwest-based fund that invests in underrepresented founders and raises about $20 million to invest in the pre-seed and seed stages. Prior to this, I did some work at a growth equity fund based in Kansas City. And then, before that, I was kind of doubling back and forth between New York City, DC, and Virginia, actually building out startups myself. So the operator turned VC looking to kind of crack the model and code in the venture capital industry.

Jannae Gammage 01:37
Nice. Nice. So in this episode, we’re going to talk about the startup hustler and what it really means. Does that imply that you need to work 24/7? Can you not work nonstop and still succeed? I definitely want to hear your feedback. But first, what motivates you? A lot of times, people say if you can’t work nonstop, you can’t do 24/7 about some of your passions, then you’re just not motivated or disciplined. Personally, I don’t believe that’s true. But so what motivates you?

Nassir Criss 02:14
Yeah, I completely agree with you. I think you know, really, it’s about level setting and figuring out what your goals are. So I know that my goals are different from yours. And our goals are different from people that probably listen to this podcast. For me, you know, I’m motivated by intrinsically wanting to make the world a better place. And as romantic as that sounds. I’m a natural-born problem solver. What that means is close to home is creating financial security, not just for myself, but for my family, my immediate community, and my friends. And the evolution of that has been throughout my career trying to do the same thing for other people that look like me, for other people that come from backgrounds similar to mine. And so really, I mean, what makes me get up every day is that burning passion and desire to say, Hey, how can I create wealth in the lives of others while also creating wealth and in my own life, and being able to go out and build right, like, I think that I’m a person that’s really passionate about getting my hands dirty, actually, like putting things together, building from the ground up. And so that kind of keeps me engaged and excited in terms of kind of going out and tackling new problems every day.

Jannae Gammage 03:18
Nice. And at Sixty8 Capital, you guys work with underrepresented founders. And we know because of a lot of various reasons why that population is more susceptible to mental illness as well as mental health issues. Do you guys have anything in place when it comes to dealing with that, and you know, just the population that you’re working with?

Nassir Criss 03:46
We don’t have a formal program. But we do have what we call a resource catalog. And then we’ve also set a culture of openness and transparency. Whenever we onboard a new founder to our portfolio, we’ve invested in the company, and now we want to give them access to the many resources that we have available to them. We have a dashboard built out that has mentors and different colleagues from around the industry and other founders. It’s all built out into a dashboard where you can reach out to people and talk to them. These are all people that have opted into our resource dashboard to say, hey, you know, we want to be able to talk to your founders and have office hours with them. And it could be other investors. It could be industry leaders. So I wouldn’t say that there’s anyone in there that is specifically a mental health professional when there’s a community where it’s okay to come and talk about the struggles you’re having, especially as it relates to you trying to grow and build your business. Secondly, you know, I think Kelly Jones, who is the GP and Managing Director, as well as co-founder for six years, has done an incredible job of creating a culture where we all feel seen and heard. Literally, our monitors see her funding. But I think one of the things that she expresses to us is, you know, we can’t do our best work if we don’t feel like our best selves. And a lot of the times that require making sure that We are within a rhythm that we’re taking rest at the appropriate times that we’re able to get help, maybe either within the team or outside of the team and pointing us to the right places. And so that’s a culture and environment that we then also take towards our founders. And we encourage them to have not just within their personal lives within their kind of founder journey, but within their teams.

Jannae Gammage 05:20
Okay, I love that it’s not normal like venture capital firms don’t have a resource dashboard. Is that like the norm? Or is that a capital thing?

Nassir Criss 05:31
I can’t. I can’t speak to everyone else or exactly what they do. I know people have something similar, like a shoutout at 25. There in Chicago, they do this like a summit every year where they bring together all their contacts from their network. And I don’t know that someone has a living kind of database with optin context similar to what we do similar to what we have, but maybe they do. I just don’t know for sure.

Jannae Gammage 05:54
Yeah. I love it. I love it. Okay, so grind culture. And for my listeners who don’t know what grind culture is, it’s the idea that success or even status is achieved by always being on and unavailable. So like, no matter where you are, what you’re doing, you’re hustling, you’re reachable. The first thing you do when you wake up is to check your emails and respond. You’re the first person at the office, or wherever you’re working from at that moment, and you just have, like, this never-ending to-do list. There’s always something to do. And it’s almost like a badge of honor to just sacrifice your time and yourself in order to be successful. And I want to point out that for, you know, black and brown people, grind culture can have such a deep and just more hurtful meaning. Because it’s, again, rooted in systemic racism. So I want to talk about founders. The difference to you, if you are, is it called shopping? Like, what is it called? When you’re looking for founders to invest in?

Nassir Criss 07:21

Jannae Gammage 07:22
Sourcing. I knew that came to mind. I don’t know why. We’re not cattle.

Nassir Criss 07:32
These are people.

Jannae Gammage 07:32
These are people. What would you say is the difference between founders that you’ve come across that are truly just grinding it out? 24/7? And those that aren’t? Have you seen anything? Or do you even have access to that information?

Nassir Criss 07:49
Let me make sure I’m clear about what you’re asking. So like, really kind of differentiating the ones that maybe have a different type of routine, versus those that are like, it’s very clear, they’re going out, they’re getting after it like every single day.

Jannae Gammage 08:03
Every single day. 24/7.

Nassir Criss 08:05
Okay, yeah. You know what I would say that, I think, in the business overall, the model is built, that those founders that grind a lot, as we call it, are the ones that are the surest bets, right? Like, because you feel like as an investor, you know, the money that you’re putting in is protected. Because this is a person who’s going to do whatever it takes to be able to go out and achieve that goal, they’re going to be able to put in the time, they’re gonna be able to return the calls, you’re gonna be able to respond to the emails, build the product, go to the meetings, all the things. However, I think that the best founders have figured out the balance of how to do that and also still make sure that they’re prioritizing their mental health. And so I think for us, a lot of our process, in the beginning, is spending time with the founder to actually get to know who they are, right? Like, the investment process can move quickly. But for us, we want to have several meetings, we want to get to know the founder, we want to know why they’re motivated to do what they’re doing. We want to know what their background is, how they’ve assembled their team, who they are, and what their team thinks about them. Right? Like, we’re not digging into stuff like their families and things like that, like maybe over drinks or like dinner. Yeah, like maybe over dinner or drinks or something like that, you know, obviously, like, once we get a little bit more cordial, we start to share things, but really, it’s about understanding, like, do you have a balance in your life that allows you to be able to give maximum effort to the business in whatever capacity that you can, while also still taking care of yourself because at the end of the day, like the founders, the most valuable asset to the business, at least until it grows to a certain level. And if our founders are not in a position where they’re well taken care of, then it’s of no value to us. Right? And so I think that all kind of comes into play when we’re starting to think about the personality of the founders initially, and really kind of evaluating what does the fit feel like? Especially knowing the culture that we have within our team within our company.

Jannae Gammage 10:02
So how many hours a day does a seer work?

Nassir Criss 10:06
Can I say that?

Jannae Gammage 10:08
Tell me your routine. Tell me how you operate.

Nassir Criss 10:12
You got to tell me yours back too. You got to tell me yours back.

Jannae Gammage 10:16
No investors are gonna want to hear what my routine is.

Nassir Criss 10:20
I definitely want to hear. I would say that mine varies, you know, between having meetings with founders, other investors, LPs partnership opportunities, and strategic initiatives, but then also having what I call work, which is like building out financial models, valuations, doing market research, things like that. On any given day, I’ll probably put it somewhere between like nine to 12 hours. Now, that being said, like knowing that I kind of work in that capacity, I also allow myself the grace of having like, one day a week where like, I don’t work out all right, or two days a week, where I’m saying, Hey, I’m going to do half days, like, I’m only going to take meetings from 9am to noon. And then, from noon to, you know, whatever the rest of the day, I’m going to allow myself free space to think and be creative. And so, it does vary. But I feel like, you know, most of the time I’m working. And that’s a personal choice for me, right? Like, I think, you know, I take the time to be able to separate myself from my work, so that I can be in the capacity where if any of my founders need to call me, they can call me whatever, if my GPs or LPs call me, they can call me. So it’s very strategic, like how I figured out my balance. But that’s probably my routine. I’m curious to know about you since, obviously, founders like different dynamics. But

Jannae Gammage 11:37
Yeah, so it really depends on the stage that I’m at. So I’m back in like, early stage, venture, beast mode, whatever. So it’s a little different. Because I do have to be very, very intentional with setting boundaries. Because I just know how I am, especially when I’m building a new company, it’s like a baby like, you know, you in it. And you can treat it like a baby with a baby. When you bring them home, you have to get into a routine. You have to figure out what works and what doesn’t. Fortunately, you know, this time around, I’ve already had some things in place to where I can kind of fit in with my work. So every other Friday off, I do the four-day work week. And that being said, if it’s a revenue-generating activity, then I will answer. If you can wait, if you wait, I think it was really training my mindset. In the beginning, everything was revenue-generating activity in my previous company. And that’s not the case, things can wait, and things can get done tomorrow or Monday. And so I think that the mindset shift, and that’s how I keep myself kind of in tune, because mental health for me, I have, it has to be the priority, or I cannot perform, I cannot be productive. So I don’t want to be operating in a stage of burnout. We make two-week sprints and then one week of reflection planning, where we don’t do big meetings or anything like that. I myself won’t take over three meetings that week. Because I do need to reflect, I do need to plan so that I can be the best during our two-week sprint and a two-week sprint. Yeah, go hard. In those weeks, there are three to four days where I do nothing but work. And I could have a 10 to 12-hour day. But for the most part, I don’t need to. If that changes, then it changes. Also, know that this time around, I don’t have a lot of control. And it’s so early, I’m always just like putting out fires here and doing this, and my workflows are so diverse right now and ever-changing. I changed my environment. So I’ll travel while I’m working and, you know, set up shop in different countries for a month or so. And just make sure that you know, I’m operating in my happy place so that I can continue to be productive and work like that if I need to work like that. But as for my team, you know, I don’t let them do that.

Nassir Criss 14:26
I love that I would just point out one thing that I noticed about you that I am greatly admiring, and as far as it takes a level of self-awareness to be able to know that, right? Like to be able to know where your breaking points are, your weaknesses, like how far you can actually push yourself, and really how to get the most productivity out of yourself. And so, like clap, clap, clap, kudos for you. Because I think they’re like, for real. I think a lot of people don’t even get to that place where they like. Having that moment with themselves, they push until burnout and then try to recover from burnout. It is the most difficult thing to do when you are passionate about something you want to continue to get yourself to work on it. So I’m taking notes from you. I think that that’s cool. And that’s certainly something that I want to tell other founders about if you’ll give me permission to.

Jannae Gammage 15:11
Yeah, and I think I appreciate the kudos, I really do. It took a long time to get here again, I’ve been an entrepreneur since I was 14, I am 36. Now. So literally, just in the past two years, I got here, you know, it wasn’t always like this. And it did get to a point where I did reach a mental breaking point where my life was a mistake, by my own hands, and I don’t want to get back to that point, right? So now I understand it with therapy. And with, you know, my support system, I’m able to look back, hindsight is 2020 and see, you know, my air and where I did not prioritize what I needed to prioritize as far as myself. Because there is that stigma, as a founder, which we’ll get into our next question, actually, there is that stigma that like, I have to be always on, I cannot be open and publicly say like, I’m struggling, I can’t show up to work, because my employees are watching, you know, my customers are watching, I want to go raise money. I can’t be out here looking like I don’t have it together. And like I can’t pull this off. Do you know what I mean? What are your thoughts on that and your opinion on that coming from the VC perspective?

Nassir Criss 16:33
Yeah, I think there’s a couple of different schools of thoughts that are like specifically in our modern age going around right now, there’s like this idea of like, build in public, where you share everything, and like, you tweet about kind of all the ups and downs and stuff, which I think couldn’t be valuable for some people both as, like, an expressive way to communicate, but also for their audience, like the people that are listening and learning from them. And then I think there’s kind of a more traditional school of thought, which is like, you know, I’m going to build, build, build, and I’m gonna let the building kind of speak for me and whatever I may be going through, I might not say. I think different strokes for different folks, different things work for different people. My dad always told me at a very early age, time and place, and he was like, you know, know what you’re saying and who you’re saying it to, and know that sometimes it might not always be the right time, if you’re in the right place, sometimes you might be in the right place, and it’s not the right time. And so like, what that’s just impressed upon me. So like, not everything is for everyone all the time in every place. So I think as long as you do it, my kind of impression of it is like in this business on both sides as a founder and a VC. It’s very strategic. So as long as you kind of know who you’re talking to, while you’re talking to them, is it the right time to be sharing the right information and things like that, while also being transparent and honest, open? I think you can’t lose, I think it’s a balance. Like, I would never tell anyone to like not show up and not tell the truth and omit information and things like that. However, you know, again, maybe there’s more personal things that are going on in your life that you might not want to share at that moment. However, like if it maybe affects investment down the line, is that something that you have to think about? Like, I think it plays into a lot of different things. But for the most part, what I can say about our team, specifically between Kelly, Paul and myself, we try to be as open and transparent as possible. Like the 68 model is transparency, VC itself is already cryptic enough, like we shouldn’t be trying to withhold information, especially from a lot of founders who are like this is their first time trying to really go and raise institutional capital, and don’t necessarily get feedback on how to walk that journey, or how to how to go down that path. And so we preach transparency, obviously, are we sharing, like LP docs, like openly on Twitter and stuff like that? Not necessarily. But I think that everyone on our team would agree that if any founders came to us with questions, we are very direct, we’re very open. We’re very honest about our process and how we do things.

Jannae Gammage 18:57
Yeah, I love that. This is a good time to say, you know, speaking as far as burnout, if you’re looking for expert software developers, that doesn’t have to be difficult, especially when you visit where you can build a software team quickly and affordably. You can use the platform to find your technical needs, and then see what available developers, testers, and leaders are ready to join your team. Visit to learn more. Are you familiar with Full Scale? Like have you ever been on that platform?

Nassir Criss 19:28
I don’t think I’ve been on it directly, but I know about Full Scale.

Jannae Gammage 19:32
Dope. It’s super dope. I would definitely. I mean, recommend it to your portfolio companies. If it’s something you want to do. I don’t get paid for this. I’m just here. Obviously. I know Matt. It’s a good setup. I like the way he has positioned it for tech startups.

Nassir Criss 19:52
We have another founder in KC, I think, that shortly it actually works with this doing something similar, I believe. Is Lee building out a similar platform?

Jannae Gammage 20:03
Nah. No, I don’t think so I think it’s different.

Nassir Criss 20:09
Oh, we could talk about that.

Jannae Gammage 20:16
Let’s see my questions, potential risks, health risks of grind culture, I want to get back to that, because I am honestly, in one of the reasons that I started addressing, you know, the mental health epidemic for entrepreneurs, outside of myself, and my previous struggles is that I’m so sick of getting on Instagram and Twitter, and wherever else Snapchat, whatever your choice, choose your flavor, and seeing these entrepreneurs posing in front of the Lamborghini, you know, promoting working 24/7, and just this unhealthy, unrealistic battle rhythm of getting to a million dollars or $50 million. First of all, a lot of people think they want $50 million in their account. You don’t, you don’t even need that, like there’s why are you working? What are you working for is the first thing, but to just the risk, I want to just reverse and show that it can be different. Do you know what I mean? Like, you can work, you can do what you have to do, you can grind it out, but like the whole culture behind it is becoming so unhealthy, and so unrealistic. And it’s not even real. A lot of those times those Lamborghinis are freaking rented, like, if you go and get a photographer with the droning stand in front of a Lamborghini is like, yeah, I’m successful. Let me show you how to make six figures. It’s all marketing. But that marketing as far as selling courses, and things like that, is what they use. And they put this picture of success. And it looks just like that, you know exactly what it looks like orange Lamborghini or green?

Nassir Criss 22:08
I know exactly what you’re talking about. I see it on my explorer page all the time.

Jannae Gammage 22:14
Wherever like that is the picture of success now. And it’s bullshit, honestly.

Nassir Criss 22:20
Yeah, I would agree, I think. So what we’re kind of getting at is this idea of like people preaching, really what’s an unhealthy form of work, and then attaching it to a lifestyle that they know most people most people dream of, right? But what it is, is a false narrative. Like, I think, again, I can only speak from my perspective. But what I’ve seen is, everyone that’s successful has their own routine, like you and I both know this, because we’ve tried to get things off the ground many times, like, yeah, there’s a phase in time where you have to be working, right? Like, you have to be trying to make it work to figure out what’s best for your customers, various stakeholders, your team, like you’re on any given day as an early stage founder, especially when you’re by yourself wearing probably 25 hats. And there’s some of that you just have to go through. Yeah, but what’s not communicated enough, which I think is something that you’re trying to solve, which is like a beautiful, it’s beautiful to kind of watch your process of like you bringing light to this is like, who’s talking about balance, who’s talking about going and seeing a mental health professional regularly, so that you have someone to talk to who’s talking about rest, and replenishing, who’s talking about hobbies and exercise and diet, right? Like, there’s not enough people that are wedding those things together, and being like, hey, what actually makes me successful entrepreneurs, not just the person that’s willing to put in the work, but the person that’s putting up with willing to put in the work on themselves, so that they can stay healthy, so that they can continue to provide for the longevity of things. And I just think that that’s not talked about enough. I think that there are too many people who are just committed to doing what they see, and are doing what they think that they’re supposed to do formatively. And oftentimes they hit a wall, they hit that wall very quickly. And because they haven’t built a foundation to really nurture themselves, it’s difficult to kind of go back around. So I think, you know, what, what, you know, our work is based on kind of what we’re both doing. And then just even how we care about the communities. How do we shift the narrative? Like how do we start having conversations about what it means to both be ambitious, hardworking, regular, consistent, but also healthy, mindful, and aware? Accepting restfulness, right, like, like, what are those conversations like? And how can we start to what I would probably coin like build out the holistic entrepreneur, that person who is able to both take care of themselves and their business, because I think that as we move further and further into the future, those are probably going to be the people that are the best poised for success down the road. Obviously, it sounds like you’re, you know, you started to develop that process and you are one of those so it’s like, how do we create more journeys and like, how do we find more of those and be able to encourage them to do that?

Jannae Gammage 24:58
Well, there’s only one me.

Nassir Criss 25:04
You’re right.

Jannae Gammage 25:06
No, no, no, so I’ve been looking for the solution for a while. And I think I’ve just come to the conclusion that the same way that you know, you know, Alexis Ohanian calls it actually hustle porn.

Nassir Criss 25:24
Yeah. Wow. I didn’t know that, that he called that.

Jannae Gammage 25:28
Hustle culture. He calls it hustle porn. It is so true, though. Because it’s just so attractive, right? It’s like, you can’t, it’s like, I gotta have that. And, bro. Like, if you’re starting a tech startup, first of all, you do not make a million dollars yourself personally, to go buy a freaking Lambo and do all those extra things for a while, if ever.

Nassir Criss 25:49
For a long time. Like relatively, it’s a short time in the grand scheme of things. But it’s longer than like, I started this startup and six months later, you know, there might be some cases of that somewhere. So I don’t want to say it’s not possible, but that’s not the norm.

Jannae Gammage 26:04
Yeah, it’s not the norm at all. Um, and it’s, is it really something even I guess some people do want the Lambo. I just realized, like, the way that you do it is the same way that they did it, they created hustle porn, you got to create holistic porn, you got to make this lifestyle seem just as valuable and just as desirable as standing in front of a Lamborghini with it. And I travel, you know, I mean, but I’m doing the things that make me happy. And when, when people can see like, that is genuine, like, you are truly living your best life and whatever that looks like for you. Maybe your best life is being with your family, which is a part of me living my best life. I can spend time with my family and my daughter, whenever I want. I go to every soccer game, I go to every practice, I go to my wife, like, you know what I mean? If they want to travel, if they want to go somewhere, we’re going. And that’s good enough for me, I drive a freakin ‘Jeep, you know, I’m saying she drives a fancier Ali’s school fancier than me, but we don’t have Lambos, we have a house. Well, we did have two, two residences. But those are the things that make us happy. Those are the things that complete us being able to say, I’m going to change my environment, because I’m back in hustle mode, startup mode, early-stage mode. And that’s really the only thing that I can control when it comes to my schedule. And how my day goes, is because I started to focus on what makes me happy, and I was more productive. And I was doing more revenue-generating things, it was just like a, you know, a domino effect. So I want to know, your, your, your mental health routines, what do you do to get in a space where you can continue to work the way that you work, that you continue to be productive, and help entrepreneurs and live your purpose.

Nassir Criss 28:05
First and foremost, I have to acknowledge the fact that I’m a person of faith. So for me, that is like core to my values and what I believe in, and the higher power that I believe in. And so, you know, I start every day with prayer and meditation. I know for a lot of people like maybe it’s not an entity, maybe it’s like the universe. But there is this calling, that’s you know, we’re all interconnected to something that’s beyond us. And that’s what helps me kind of keep my purpose at the forefront of my mind. So before I even look at my phone, emails, anything like that, I get up and I do a 20 minute prayer and meditation. And it’s really about setting myself up intentionally for the day and being very direct. And this is what I want to accomplish. This is how I want to accomplish it, but also expressing gratitude for a lot of the things that I do already have in my life. Like that gives me a calm and an internal peace and then allows me to kind of go out and I always say conquer. I do have therapists that I see once a week when I was going through some tumultuous times. I’ve now kind of spread it out a little bit more. So now it’s once every three weeks. But she is incredible. She is also a black woman shadowing my black women. I think that there is something special to be said about having a black female counselor or mental health professional, especially as a black male who oftentimes has difficulty in expressing some of my innermost thoughts to either my counterparts or my homies Right. Like it’s you can have those conversations and be really intimate, but it’s beautiful when you have somebody across the table that’s professionally trained. And then I try to really give time to prioritizing things that are important to me. There are people out there in Genet. I’ll tell you right now they’re like, I don’t want to sleep. Sleep is for the weak that I sleep like they can. They can have that like I’m like, if I could start an idea at 10am. I would work till 10pm. Because I feel like I want that time to wake up and be able to have breakfast and exercise. Now, yeah, obviously I can’t always do that because I work on East Coast time and to be early is really to be late. So it’s like I do have to get up. But I prioritize sleep if I can get in 30 minute power naps every now and then I try to. And that’s a little bit more to be transparent about my process. Exercise is huge for me. I love fitness, like I love getting out. And even if it’s just taking a walk, I love going to the gym. So like the process of those things, as well as being able to acknowledge when I need rest, like being able to say to my team, hey, I may need two days to not take any external meetings. And then also having an incredible team that can slide in and be able to kind of hold that weight while I’m gone. Has been great for my process in terms of setting myself up for success and being able to prioritize my mental health.

Jannae Gammage 30:58
I love that. I love it. I love the faith thing, too. I’m one of the universe’s people. But I was raised non denominational. I was raised in church four times a week, you know, whatever, that type of kid.

Nassir Criss 31:12
Using church boot camp, they had you in church.

Jannae Gammage 31:15
My dad is a pastor. You know, and I’ve kind of come into my own, but I do believe that you should have some type of higher power or something that you look to, to kind of keep you grounded. It’s so important. Doesn’t have to be religion, but you need something to keep you grounded. You know, I honestly don’t trust people who are just out here willy nilly, like, what keeps you accountable? Like what keeps you these are facts? Morally like, sound? What I feel like you need something, if it’s not your family, if it’s not religion, like what is it, you just desire, I gotta watch you blowing in the wind, just booting flapping in the wind. I wanted to say, and this will be my first company where I raise money. And I want to hear your feedback on the preventative measures that I feel like I’m taking to get there, and maybe some of our listeners can take this, if the feedback is good, or you know, whatever. But one of the things I know is that, you know, when you’ve taken on investment, specifically VC, you guys are looking for growth, right, you want to return on your investment, anybody. And that can be a slippery slope, because he put a lot of pressure on us as the founder, we feel like, like I have to get this insurance I have there, I have to be held accountable. There’s money involved, you know, there’s cap tables, everything. And then that kind of filters down to the rest of the team, right? Like, people see me showing up earlier and doing these things. And then I’m looking at everyone else for KPIs and, you know, checking my email obsessively, and just the healthy boundaries that you set in the beginning, they start to kind of fade away, right and then it does become performative exhaustion. Hustle porn is what Alexa says, eventually the entire company culture just becomes or can become, which I have seen before, more competitive and political, and like the value in the team is placed on productivity, rather than, like quality, quality, or, like a sustainable output. And then everyone’s quitting. And, you know, startups, you hear this a lot that just the turnaround, or excuse me not to turn around. It’s like a revolving door for employees to quit because the culture is just so toxic or whatever. So for me, I have implemented kind of a flat structure for as far as organizational models are concerned and just very collaborative. Everyone has voiced that my intern gets on some meetings, you know what I mean, and gives input. And I feel like for me, I think it helps people continue to feel valuable. We’re all working towards the same goal, and it becomes less of me looking like, what’s everybody doing? And everyone’s just kind of on the same page, you’re on the same team. And I hate when parents are saying, we value culture and you’re part of the family here, because that’s bullshit to me. It doesn’t matter if you don’t structure your company in a way that defines success as more than just productivity. And it’s more focused on value. What’s your thoughts?

Nassir Criss 35:04
That’s a loaded question. And there were a lot of things in there. So let me try to figure it out.

Jannae Gammage 35:09
I went off into a rant.

Nassir Criss 35:12
Let me try to figure out exactly what kind of attack here. So the first thing that I tell people is to know your business very well, because I think that from the outside, a VC can look very attractive. However, VC is not for everyone. And oftentimes I find myself explaining to particularly founders of color, what VC is how the model works. Although there are firms like us that are trying to disrupt that model, there are some nuances of just how the business works and its nature that are not suited for all types of businesses. So there is, you know, I wouldn’t call it pressure but a responsibility anytime you take on money from an investor. And that might not even be an institution that could be like Angel investors that come in that have varying personalities, like you get an angel investor who wants to put the money away and not hear from you for five years, or until you raise that next round. But then you get the angel investor who wants to be an operator with you, and you know, signs, operator agreements and things like that. And so knowing, like, what you want to get into and knowing your business very well, and knowing how you want to scale is like the number one thing. Secondly, though, as you are starting to look for investors, this is why I think it’s like Paramount paramount for founders to figure out the culture of the types of investors that they want on their cap table. A lot of founders think that you have to just take money, because VCs are interested in your company, especially if you have a good company. But that’s actually backwards, like VC would not exist without founders without people building the next Uber and Facebook and Twitter and Discord, and things like that of the world, right? And so it’s important that I think founders in their own way do a due diligence of the people that they’re going to have on their cap table to know, are these people aligned with us, right? And that takes like, it’s a process. It’s not just going to their website and being like, seeing that they love. They love scrappy founders that are based in the Midwest and are building great AI companies, right? Like, it’s going to those people’s LinkedIn ads, and really figuring out what your experience has been? Like? Do they have any overlapping experiences with me? Where they go to school, maybe like, do you know anybody in their network where you can ask about kind of their character, and their trustworthiness and things like that. And so I think like, those are the preventative measures that I would encourage founders to do before you get into a relationship with Him. Because it is a long term relationship. Because the worst case scenario is you haven’t researched investors, you haven’t actually figured out if your business is even pulleys for VC. And then you get into a place where you take hundreds of 1000s millions of dollars from somebody else. And now they’re coming to you knocking on the door, because they have that responsibility, that’s a part of their jobs, part of my job. And it’s like, you’re not in a position where you can deliver, right? And I think that there’s always a balance with that. And that if you find the right investors, they’re always going to be willing to work with you. Because you built a good relationship, you have similar interests, you have similar mindsets about how to attack the problems. And so you’re not really getting into the kind of tit for tat, where it’s like, it feels like it’s just a job. That all being said, though, Jannae, I cannot be I would be remiss if I didn’t say that sometimes VCs you have to be bad guys, right? Like, sometimes. There are things because we have bosses, too, that people don’t understand our LPs are our bosses, right? And we are in charge of their capital. And we’re in charge of deploying that capital in the best way with minimal risk.

Jannae Gammage 38:39
But can you for the listeners that don’t know? Can you let us know what an LP is?

Nassir Criss 38:44
For sure, yeah, so limited partners, our LPs are limited partners. And these are people that invest in VC funds on behalf of other investors, right? So these could be endowments, it could be major corporations, it could be high net worth individuals, anybody that wants to put their money into the asset class to see it grow over a long period of time, relatively quickly during that period of time, with obviously, opportunity for massive returns. And so LPs are really who employ VCs.

Jannae Gammage 39:19
It’s important to know that because it gives a lot of founders that don’t know and they don’t have the perspective that just like you’re asking for investment, VCs have to go out and raise investment as well. So they’re not investing in people just because they like you or because or not investing because they don’t like you like they literally have to have ROI just like you do, so that they can go back to these LPs and continue to raise funds and continue to invest on the other side of that. What I always say is founders do not forget that you play a role in this and you have a voice. As much as I love nice things like if we started an investment foundry relationship, I wouldn’t just take his money, or excuse me, Sixty8 Capital’s money, just because it’s there. I was gonna say my pack is empty, right? I got it. But I have a voice. I understand ecosystems both because founders come up with great ideas and the greatest and brightest minds are coming up with the greatest ideas. And VCs need those ideas to invest in. So it is a mutually beneficial relationship. It is not just what the VC says, or what the angel says, or even what the bank says, you are going out, you’re working hard. So sorry to cut you off. I just, you know, I just say my piece.

Nassir Criss 40:40
No, that’s, that’s beautiful. And I would actually disagree only on saying it is beneficial on both sides. But it’s skewed in favor of the founder like the founder is the most valuable asset in the entire thing. Right. And I, like I’ve said that multiple times in this conversation, but it’s like, I’m all about empowering founders to take that power back. And to just kind of be like, hey, look like, we know that we’re the ones like you said that are going out and hitting the ground every day and building out these companies. It’s essential for founders to do their due diligence to find investors that are aligned with the clauses and missions that they also want to serve. Yeah. Otherwise, you’ll be in a relationship that you can’t get out of. That’s a negative one.

Jannae Gammage 41:19
So that would suck. Have you ever been married? Somebody you want to be married to now? All right. We’re at the end here, so you don’t have to spit off some questions. One-word answers. Or you can tell a story whatever you want.

Nassir Criss 41:36
I’ll try not to tell the story. I’ll be going on and on. I’ll try that too.

Jannae Gammage 41:39
Okay, um, what defines a win for you?

Nassir Criss 41:50
Oh, when is making sure everyone around me eats?

Jannae Gammage 41:53
I love it. NASA philanthropist? Do you consider yourself driven or obsessed?

Nassir Criss 42:04
Somewhere in between the two? You know when Drake says somewhere between psychotic and iconic?

Jannae Gammage 42:09
Oh, awesome. Bring me to my next question. If you’re trapped on an island and can only hear one album, what would it be?

Nassir Criss 42:19
If You’re Reading This, It’s Too Late. You know, that’s my favorite because I said it.

Jannae Gammage 42:26
I know very, very little. What’s your superpower?

Nassir Criss 42:33
My ability to listen? Kryptonite. Sometimes I’m too emotional about things. What’s your sign? Queries about you?

Jannae Gammage 42:49
I thought I was the emotional one. Cancer. We’re both pretty emotional, though. That made me lose my question.

Nassir Criss 43:00
Take you down a path. He wasn’t ready to go down.

Jannae Gammage 43:02
Yeah, start thinking about stuff. Okay. Describe yourself in one word. Relentless. Describe me in one word.

Nassir Criss 43:16

Jannae Gammage 43:19
Describe entrepreneurs in one word.

Nassir Criss 43:23
The good ones are the ones that fizzle out. I’m kidding. Entrepreneurs are tenacious. You have to be able to go out and go against the grain and build something. And really stick to it even when it doesn’t necessarily always feel like it’s working out.

Jannae Gammage 43:39
I love it. I love it. Any last words? Before we jump off of here?

Nassir Criss 43:45
Have to shout out to Nick. Thank you so much. And also for us. I have to shout out to the Startup Hustle crew. Sue me as I’m recording today. And also want to shoutout to Kansas City for being one of the best startups.

Jannae Gammage 43:59
Yeah, baby. Where can everyone reach you, and where can they find you?

Nassir Criss 44:04
LinkedIn and Instagram are my two probably most public-facing social media sites, @nassircriss, first name, last name, no spaces, dashes, underscores. That across all my social media, reach out, follow DM, all the things. Or hit off Jannae, and then she’ll give you she’ll be like contacts.

Jannae Gammage 44:21
Really? Well. I’ll give him my cell number. Oh, no, no, no. Okay. And that’s Criss, not cross.

Nassir Criss 44:30
Border. No, let him know. Maybe try to say no. See your crises.

Jannae Gammage 44:36
Looks like people anyway. All right. Well, thank you so much for closing out my series. I really appreciate everyone for listening. I have had a blast. Stay tuned because I will continue pushing out this type of content about mental health. I have a lot coming up. I’ve been really silent. We’re just about to get real out of being here. You know, thanks again for having me. I didn’t curse a lot, so that’s not normal, but you know the message. We don’t want to dilute the message with curse words. Alright, y’all, have a great one. Keep hustling.