074. Never Give Up! An Inspirational Interview with My Client Sydney Montgomery

Welcome.

I am marketing expert and business coach Melissa Kellogg Lueck. And this is the Doing Business Like a Woman podcast where we are exploring and teaching you how women are reinventing the way business is done and money is made to help you create greater impact and financial freedom one business at a time. Awesome. Well, I am so excited that you are all here with us today for a very special episode. I have with me today my now, I have to say, former client, Sydney Montgomery.

And.

We'Re celebrating because, yes, she's now a former client, but we're celebrating a graduation of sorts because she's come to a place in her life and her business where it's a much bigger game and she has grown so rapidly. We, we decided, we started working together in 2020 and. But I wanted to bring her on because I think she's such a beautiful example of what is possible and also so inspiring. Such an inspiring leader and a growing entrepreneur. And so I wanted her to share with you all what it, what it's like kind of, you know, on the, the growth side, on the other side of a lot of this early years of growth. So. So welcome. Sydney, would you like to introduce yourself?

Yeah, absolutely. And I don't know if I'd say on the other. I'm fully on the other side. I'm somewhere. I'm not where I was. I don't know if I'm on the other side yet, but I'm definitely somewhere. But yes. So my name is Sydney Montgomery. I am the CEO of the EdTech Startup Outline, which is an interactive writing platform for students to help them write better structured essays. And I'm also the founder and executive director of the Barrier breakers nonprofit, which is a faith based 501C3 that has a mission to increase access to and support in higher education for BIPOC and other marginalized students. We specialize in working with first generation and minority law school applicants. And to date we've helped about 4,000 college and law school applicants on their journey to higher education.

Awesome. That's a mouthful.

Yeah, I've gotten really good at it. You have?

Yeah, she's been doing lots of presentations and we'll hear more about that later. But let's just kind of start at the beginning and tell us a little bit about your origin story, your cultural background, like your upbringing and where you come from.

Yeah, so I'm from Montgomery County, Maryland. I would like to say born and raised, but I was technically born in D.C. my parents were both in the Navy. That's where they met. And my mom is a Jamaican immigrant and I have a younger sister who's 11 years younger than me. So that makes our family unit, although my parents are separated, so it's a larger family unit, blended family unit. But I basically, like I said, I grew up in Montgomery County, Maryland. Grew up kind of lower, lower middle income, kind of very flexible terms. I ended up becoming the very first person from my high school to go to Princeton. And then I went straight from Princeton to Harvard Law School. And I really only got there through really the grace of God and also my teachers who helped me because I didn't know what I was doing when I was applying to college. I just had a random list of schools, mostly based off of Gilmore Girls. I really didn't know anything about the college application process, but going to Princeton changed my life in so many ways and it inspired me to kind of give back and, and I started working with students at my high school and my church and my community on the college application process. Didn't really, really know what I was doing, but knew that there was a lot of misinformation about what kinds of students could get into these highly selective schools. Like, I didn't have straight A's. We also didn't have a lot of money and people were like, oh, you can't apply to those schools, you'll never be able to afford it. But Princeton was the most affordable school that I got into because of their generous endowment and financial aid. Wow. And so really? Yeah, I mean people don't, they don't know that like Maryland would have been significantly more expensive, which is, is a shock for a lot of people. And so I wanted to kind of spread that correct information because I, you know, growing up in Montgomery County, Maryland at the time, it was one of the best school systems in the country. But we weren't really seeing a lot of students going to the Ivy League and certainly not students that looked like me and wanted to be part of changing that. So I started just working with students. I did that all through college also because I've always worked multiple jobs. I've worked at least two jobs since I was probably 15 just because I needed to. And so I, you know, I worked that while I was in college along with some other campus jobs. And then when it came to going to law school, my pre law advisor was very instrumental in helping me get to Harvard. But then she ended up leaving my first year at Harvard. And so there was a, there was a gap. There were a lot of, again, first gen minority students that didn't have any guidance on the law school process. So I started getting into law school consulting. Realized when I was at Harvard that, I mean, there were just so many doors that were really open for me because I had the right information that could have been open to someone else if they had also had the same information. And started. Started looking at what admissions would look like as a profession. But knew that my plan was to come home to Maryland to practice family law. I wanted to be there for my sister who was going into high school. And so I came home. I was clicking for a judge, but then also realized, you know, if I'm going to be consulting students, I want to do it right. And so I got my certificate in independent educational consulting from UC Irvine while I was clerking, and then joined family law practice. But I also developed a lot of health issues at that time, which I'm sure we'll talk about. And so ended up making the decision right before the pandemic to leave the firm. I mean, I really was put on an unpaid medical leave. And so I. It was. I was pushed, but I left.

And other plans for you?

Yeah, yeah. God was like, go. And I had. I had prayed to God like my church had done, like, pre 21 earlier. And I had prayed like, okay, God, if you just, like, I really just want to consult full time. But I felt like to be an entrepreneur, you had to have six months in savings and all of this other stuff. And I just had a lot of debt and no savings. So I didn't think that I could be an entrepreneur. I thought, maybe that's something I'll do when I'm 50, like, once I'm financially stable, that I can think about, like, working for myself. But I had said, you know, if you. If you allow me to consult full time, I will use the business to grow the kingdom. And so that was the prayer that I made in January before I even knew that I'd be pushed. And then Covid happened, and then I was like, cool, well, I guess I'm consulting full time. And I'd written my parents, like, a five page business plan about, like, how I would. I love how I would, like, not starve. Yeah. I was like, these are the reasons why it'll be okay for me to do this. And ended up using that space to. I wrote some articles about consultants using their power and their privilege to break down systemic racism in education. Also ended up realizing that there wasn't a lot of representation and law school admissions consulting for people of color, women of color, just not a lot of consultants in the space that look like me. The business kind of expanded super rapidly. That was the year that I met Melissa, because I was super overwhelmed. And so let's just pause right there for a moment.

So then this is when our worlds collide.

Boom, boom.

And I met you in a Facebook group, which I had started networking in Facebook groups because all of the networking I was doing in person was obviously not happening, because this is 2020.

Right.

And so, you know, this is one thing that I teach a lot of my clients early on in building their businesses is like, go start talking to people in Facebook groups. And so here's a really great example of a person I talked to in a Facebook group.

Yeah, I think it was like the business boutique Facebook group. And I feel like I asked some sort of question. What about taxes? I don't know. What I asked. Was very overwhelmed. I was very overwhelmed. And you. You, like, responded and reached out to me, and you were like, do you want to just have a chat? I was like, sorry, yeah. Yep. And then. Yeah, yeah, it was. It was good. It was good. I mean, there was a lot of rapid growth. So I went from being a solopreneur in 2020 to having a small team in 2021. A small growing team in 2021. We launched a podcast, break into law school, and a YouTube channel. I, you know, I was working also with a video coach on that, and Zaylee Barclay. She's amazing. And then ended up at the end of 2021, being like, you know, I just really want software. And we had been talking to, you know, someone, a group that decided to invest in us. And so we had, like, our first quote, unquote investment. I didn't really know what I was doing, but we could use that money to then start the process of building software, which originally I just wanted for my admissions consulting business, but ended up growing into thinking about what does it look like to pedagogically teach writing to children? And what does it look like to engage teachers and what does it look like to build a classroom tool? So very different questions from just admissions, but that, you know, 2022 was definitely a learning, like a growing pains year of trying still to extend the consulting business. You know, at this point, we were working with at least 100 students a year and also trying to grow a software company. And what. What does that even look like? And getting a really large marquee client and having to deal with that. And so then we decided at the end of 20 that we would split the businesses and so the software company would, which Outline would be a. Continue to be a venture backed Delaware C Corp. Of which I'm the CEO. And then the consulting company would go underneath the barrier. Barrier breakers, nonprofit organization of which Melissa is also on the board. And it's been really great because they can both thrive. Barrier breakers can continue to help the population of students that I most care about helping and taking donations and get external funding. And Outline can be a software company and do all the things that a software company needs to do and work with selling into schools and that area. But I will say that. So I guess it sounds like I'm on the quote unquote, other side. I mean, they're both still building, they're both still growing. It is still definitely hard because we're not at that, like, you know, oh, we're an established company with millions of dollars coming in every year. And I'm no longer thinking about funding like, I am still thinking about funding like every day for both businesses. But I would say that the skeletal, the skeleton is. It's formed right. Like they are businesses with the definition they might grow, but there's definitely definition there. And it's no longer a question of like, what are we building, but just how do we keep executing basically on the vision and how do we become financially stable in doing that?

Yeah, yeah. I think it's so fascinating because a lot of the women I work with and talk to are like you were when we started working together. Like, they know what they want to do, they have the business and they're maybe they're in the five figure, maybe mid five figure range. They, you know, think the end all, be all is going to be getting to six figures.

And like.

She'S shaking her head. So just a quick side note, we are recording this in a video and it's posted on YouTube. So all of you listening to the podcast, if you want to see this conversation, it's, you know, in living color, come on over to YouTube anyhow. So I guess that's what I mean by like the other side. But it's like your business. So it's. You never really get to that point or we haven't seen it yet. I haven't. I've been in business 18 years where we're like, okay, smooth sailing. I'm just gonna sit back and rest. Like we're always growing and always experiencing growing pains in some way, shape or form. Right. It's just like, yeah, it's always the 50. 50. It's just a different 50.

I would agree with that. And I think, I mean, I. I have to tell myself that there's a place that feels less like. That there is a place of, like, more financial security in your business as you get further. It's funny because the word startup is very vague, right. I was talking to someone yesterday who used to work with Credit Sesame, and she was like, well, Credit Sesame is still technically a startup. And I'm like, y' all just throwing words on things. There's no way that my startup and Credit Sesame here, both still startups. Like one of one is not like the other. But no, I mean, I think like one of the joys of being in an early stage startup and being in the VC world is learning that there are a lot of companies that seem super established that are still startups. But I do think there is a difference when you have it's all about Runway, I think more than money. At least what I've learned in the startup world, it's about getting to 12 to 18 months of Runway, which we're not quite there yet. So outlines, venture backed. We've raised a little under $900,000. We're going to close our pre seed round fairly soon. But my goal is always to say, how do we have 12 to 18 months of Runway in the bank? It's kind of like when. When Roku was affected by the Silicon Valley bank situation and they had lost temporarily, like billions of dollars. Like, truly scary. But they said, you know, they. They had two years of Runway, and of course everyone's been made whole from Silicon Valley bank. But like, that is kind of like the gold standard for me is like, you know, we. I mean, not that I want to lose billions of dollars, but something could happen. And I know that we'll still have like 18 months to two years of Runway in the bank. That's definitely my goals in terms of financial stability for. For either company. Mm. Yeah.

And I think that's something we can even begin practicing even when we're in the five figures. Right? Like start.

Absolutely.

Reserves. Keeping those reserves aside and just making that part of our habit, I think would help.

Yeah. And it's something you can do whenever. Not that I have achieved it. I have not achieved it. But I think just to think about it, right, to figure out, like, how to have that cushion would be really, really good. At least for me, for my own peace of mind.

Yeah. And also that your peace of mind, I mean, literally exists in your mind.

Right.

Like you can create that sense just having that trust in yourself. And I think that that's been, for me, like, such the greatest joy for me in working with you is watching you learn and grow and trusting yourself and, like, stepping out in your power and saying, this is what I want to create. This is how I'm going to do it. And not that you're always, like, so decisive, but learning how to, you know, learning how to trust yourself, like, saying, this is what I want and trusting yourself and making decisions. Maybe talk about that a little bit.

Yeah. So I always tell people when they ask, what's the best business advice you've been given? It's always like, something that Melissa told me, which is, you make a decision and you make it right. It was so helpful for me because I had chronic indecision. I still am a little indecisive as a person, but definitely had a lot more indecision growing up. Just needing to always panel out all of my thoughts and feeling uncomfortable deciding to do something that someone maybe didn't agree with. And I think I've been forced to do that repeatedly in the last three years of starting and growing both of these businesses, because no one ever really agrees, but. And some decisions turned out to be the absolute right decisions, and some decisions turned out to be maybe not the right decisions, but you still learned from it. I mean, I think even about the business, right? Like, there was. I could have just started a completely new C corp for outline. I could have chosen to keep them both together. Even still, I could have decided to make one like both of them for profits. I could have decided to do a lot of things, and people had a lot of opinions, and there were not, like, not everyone was like, oh, yeah, forming a nonprofit, like, that's the way to go. That makes sense. Like, not everyone said that it was absolutely the right decision. I have no regrets about this decision. It's hard, for sure, but this was the right way to go. But I had to. I had to feel comfortable with it. I think there are some times when even in this process, I've made a decision that would counter to what I think I thought. But it was kind of like what people were saying to do, and then that's the worst, because if it doesn't work out, then you're like, man, I really should have gone with my own gut. At least if I make a decision and it's not right, I have no one else to blame. It's just like, it seemed like a good idea at the time, and it maybe was, and for whatever reason, it's not a good idea now. But I can stand on that. I also think that when it's my decision and people know it is, and I have the conviction, then people kind of rally to make the decision work in a way that. Because they trust you. Right. And that's something that my investors actually recently said to me lately. We have some big decisions coming up. And overwhelmingly they were like, you know, whichever way you go, I'm behind you. You know, I. I trust you and I'm behind you, and you have my support in whichever decision you make. And I think at that point it's like, that felt really good. And also knowing that, like, it's not about really a right or wrong decision, it's just a path that I have to pick and kind of making it right. The last thing I'll say about it is, last night my boyfriend and I watched everything, everywhere, all at once. And if you haven't watched that movie, was it good? It was good, but it was an experience. It was an experience.

So be ready for an experience.

Yeah. Yeah, yeah, yeah. Michelle Yeoh earns all of her flowers. But, like, there's no spoilers. But one of the concepts is also that, like, every decision in life that we make, like, a small tweak could put us on a completely different life path. Like, one small decision is, you know, could have put your life in a very different trajectory. And I think that's so interesting too. And it's not that any of those life trajectories were necessarily better or worse than the others. They were just different. And they each had pros and they each had cons. And I think that's the same way with business. It's not about a right or wrong decision. It's just they're. They're different. And if you do one decision and things might go that way, and it doesn't mean they can't come back, but, you know, just learning to live with whatever path that you choose at that moment.

Yeah. Yeah. It's like accepting where you are because it is where you are. Right. Not fighting with reality or Right. Or like, wasting energy thinking about what might have been if you would have gone the other way. Like, it doesn't matter.

And 10 years from now, somehow all of these decisions and even the decisions that I've made that I've been like, ah, that was kind of a mistake. Like, what? I would not be where I'm at right now without even those quote unquote mistakes. Like, they're all kind of necessary stepping stones to get me here. And so I don't Know, like, if I would have changed any of those things, I don't know that I'd be here right now. Yeah.

Yeah, totally. So, on that note, tell us, like, some of your greatest lessons since we started working together in your entrepreneurial journey. What have been some of your greatest lessons?

Oh, this is hard. I have many, many lessons.

We only have an hour.

No, no, I know. I think that. I think that it's good to be optimistic, but I think that some of the stress that I encountered last year is because I was operating and a paradigm with no backup plan that I found acceptable. And so I think I did a lot of, we're going to spend this, and because we are spending this, we must make this. But then, like, that question of, well, what happens if you don't make this? And my answer was like, well, we must make this end of conversation. And I think that I probably should have had more of a conversation with myself about, well, what really happens if you don't make this? Because I think a lot of things happened in 2022, like, there was a war, the economy did all kinds of crazy things, and these are things that I could not have predicted.

Yeah.

And I think it's always helpful, like, to bet on yourself, you know, make the decision. Right. But also have a backup plan that's realistic. And I think especially when you're talking about payroll and. And hiring people. So outline has this 14. 14 people that work under outline, and there's eight people that work under barrier breakers. So in total, I'm, like, kind of responsible for, like, 22, or I guess I work for both. So maybe 20 people's paychecks, which is not, you know, at 29, that's, like, not a small fact. And I think creating good backup plans and creative solutions that you maybe don't even ever need and still betting on yourself and being optimistic is, like, the way to do it. And I think I maybe only did the latter, and I didn't do the former. And it just caused, like, that feeling of stress, I've realized, and anxiety. It comes from not knowing a plan. It doesn't necessarily come from, like, just the situation. And I feel like that's why I've always been so grateful for working with you, Melissa, because you're very quick to be like, well, let's look at the actual numbers. Let's pull out the whiteboard. Let's actually figure out what the situation is. And then I think that second part comes from acceptance, too, which for me was a little bit easier once the company split but like, there is, I mean, startup land is hard. And like all. One of my attorneys, Abraham, he always said all businesses head towards death, which is like a little bit like it's, it's a little harsh. But like the way, but the way like he's pushing me is like, that is the natural inclination of all businesses. And your job as a leader is to lead the business away from death. But if you do nothing, all businesses kind of have desire, I guess, a natural tendency. They don't naturally grow, they naturally die, is kind of his thoughts. And so, you know, we had a conversation even last week with, with my CEO and we were looking at the money and I was like, okay, we're gonna run out of money here. Like, everyone has a Runway and like we're, we're kind of post revenue, kind of pre revenue right at that intersection as an early stage tech company. It's like we're going to run out of money here. Like, this is as far as the investor. Money carries us. And just understanding like we're going to make a plan to do something, but also that is, that is an option. If we don't do what we need to do when we run out of money, then we close. Okay. But like looking that acceptance in the face and being like, okay, well, we're going to just do everything we can so it doesn't happen. But if it happens, we gave it our best. I think having that attitude has been a lot more emotionally healthy for me.

Yeah.

Than some other attitudes. Of course, obviously, like, it would be devastating and in fact, my paycheck, it would not be great. But I think not acknowledging a real possibility, not saying that's the most realistic one, but not acknowledging a real possibility doesn't do you any good.

Yeah, totally. I love that because that really is part of that, like, maturity into leadership as an entrepreneur.

Right.

I mean, we have, as a CEO, I feel like we have to hold the vision of the business and all that, you know, we're capable of and all the capacity that we have to serve and money we have to make. We hold that in one hand. And then on the other hand we're holding like the reality, like the real numbers. And we really could go underwater here. We really could go down in flames, you know, and what both of those things mean and just kind of be balancing that and planning for both of those scenarios. Not in a bat, like, like you were saying, not in a negative or pessimistic way, but it's like once we look death in the face and shed light There, then it. Our fear goes away too. Right? Like. Like, I've been there to that. That scenario, and I still here.

You know, I think that's such a big part of, like, my 2022 journey too, because like I said, I didn't really have those backup plans, but in a lot of ways, I did look death in the face. And I actually learned that, like, the answer isn't just that you spend money until you run out of money. Like, what happens when you approach death? At least what happened for us is then you find out how you borrow money. Right. Or you take people off of salary, or you see if people can be furloughed. I mean, I came off salary very transparently for five months. And I've also learned that you can overcome that. Right? We paid off that everyone's back on salary. Things that, like, you literally figure out, okay, what is the least amount of money that I need in order for us to sustain ourselves as a business? What can be paused, what can be borrowed, what can be sold? What, like, and I. It sounds again, like, super morbid, but, like, I think for me, 2022 was, like, living my worst fear. Like, what happens when you run out of money? And I think the thing that I'm the most proud of is we did not die. Both businesses are doing great, but we. And. And I ran out of money. And it's a super scary feeling. But. But we didn't die.

Yeah. Yeah. So for you, as far as your own self trust and confidence, it's like, you know, no matter what, you're gonna make it. You're gonna still be out there in the world, spreading your mission, you know, fulfilling your mission, your purpose on this earth. And that you always figure it out too, right? Like, you always figure the out.

Yeah. And I mean, and I think it's so helpful too, to know that your blessing is also potentially right around the corner. Because we, as a software company, we got most of our funding starting in October. So, like, that period of time between May and September where I was looking death in the face, we hadn't been funded yet. We hadn't been bringing in most of our revenue for consulting. It was just kind of like everything was not falling into place timing wise. But hopefully someone, if they're feeling this way, like, feels inspired, though. Like, if you just kind of hold on. Like, I think it's a scripture in Galatians that talks about, like, just not giving up and you'll reap your harvest. Right? Like, it. So much Money came in Q4 of 2022 and Q1 of this year that if I had folded, it would have just been a shame because it was like. Right. I was just a couple months away. Yeah. Yeah.

So it's like, what, like, from the future now, what would you say to past Sydney that was like looking death in the face and being like, all right, should we just, like, be done with this, or.

Yeah, I would say just like, you know, keep crying if you have to, but keep going because it will pay off. I mean, I am so happy with. With just the aftermath of that situation. And it was so hard. It was so hard. And Melissa knows. I would get on sessions and just cry. I would just cry. That's it. I would just be like, nothing's good. Can't do it. But, Melissa, you didn't let me give up. I think those sessions were so helpful because I felt so alone, even though I know that there's lots of women and lots of people whose businesses go through that. For me, I was feeling like a failure, and like, I couldn't do it. And just. I would tell myself that, like, you're not a failure. Like, this is a part of the business life cycle, and you will also learn so, so much. It's like getting a master's degree that I didn't ask for, but I learned so much from this. If you just keep going. Yeah. That's amazing.

So talk a little bit about some of the obstacles in addition to the, you know, running out of money obstacle, but some of the obstacles that you face and how you've overcome them in your journey.

Yeah, I think one of the biggest obstacle that's probably not as unique as it. I might even think, but, like, I have a lot of health issues. I was diagnosed with Ehlers Danlos syndrome, fibromyalgia, and some other undifferentiated autoimmune things. When I graduated from. Well, I. I guess when I was at the firm, so started when I graduated from law school and kind of spent two years really seeing all kinds of doctors. And, you know, when you're in business for yourself, you want to maybe reinvest some of your salary into the business, or you don't want to have a very lavish lifestyle maybe while you're in that growth stage. But for me, I needed to be able to have a certain salary in order to cover my medical expenses. And I think I also really struggled with some guilt with that because I wasn't reinvesting all of it into the business. And I. I needed certain things, and I was like, oh, what Are the investors going to think, why are you paying yourself? And I'm not even paying myself that much. Like, comparatively, I've seen CEO reports actually still fairly under. But for me, I was feeling like, ah, if the business is having issues, why am I even taking a salary? It's like, oh, because you have to live and you have to go to the doctor and you have these things that are not covered by insurance.

Yeah.

And so I think having to navigate not only the financials, but also like, showing up when I don't feel well or learning how to rest, like, and that's been something that I've been really working on a lot this year. Still working on it. But there is this mindset as a CEO, you're supposed to grind. You're supposed to be working all the time. All the time. All the time. All the time. Right. Like, people don't go into entrepreneurship to, like, rest. That's, that's like, not what they say. Like, I want to restful life, so I'm going to be an entrepreneur.

That's a good one.

Yeah. No one says that, but, like, I have to rest or I'm going to have a flare up. Right. And I think that I wasn't super great at that last year, trying to be better at this. That this year it's like, well, if I want to work next week, then I can't push myself this hard this week. Like, I have to continue to pace myself because going super high and crashing and super high and crashing is not going to make the business grow either.

Yeah, that's so good. So how have you dialed back? How have you been? Like, what are some of your, like, strategies for having? I mean, obviously knowing if I am going full throttle, then I'm going to pay for it next week. But what strategies have you used that have really worked for you and taking care of yourself and getting that rest and protecting yourself as the asset?

So one of the things that I've done this year is like, intentionally cook dinners, which sounds wild, but I've, like, really struggled with the whole food thing for a little bit. This is probably a very, like, it's a very late 20s thing to struggle with.

No, I struggle with the same thing. It's so funny because you're talking about this. I'm like, oh, my gosh, she's speaking to me. Because, yeah, I, I work, you know, work all day. I have two kids and it's like, at the end of the day, the last thing I want to do is cook dinner. Yeah, I have to because there's human, other, you know, small people here that need to eat. But I'm like, I would be fine with just eating, like, a bowl of potato chips and, you know, popcorn, I don't know, salad. I. No, for me, it's like, I could eat a salad and be done with it, but I don't even know if that's enough.

But, yeah, yeah, no, I. There. There was a point in my life where dinner was either McDonald's or it was like, takeout from this Thai restaurant. And that was it. Like, I didn't think about it. I was like, this is two places. I ordered on Uber Eats. Obviously not helpful to my health. It's interesting because we had actually hired someone to come help a little. A little bit with, like, mail and meal prep. And that was great and a good decision. And if you have to make that decision, like, you should feel comfortable making that decision. But then she ended up not working out, and so I was stuck with the question of, like, do I try to find someone else? And I kind of be like, you know what? Like, I'm just going to, like, let's just see. Let's just see. And I sort of changed my mindset a little bit because I realized when I cooked dinner, my boyfriend and I could sit and, like, have a nice hour or so, just, like, catch up and reconnect. And we both, like, he's a PhD student, and he gets home a little late. And so sometimes we're both just so busy that we don't actually intentionally have that time. And so I kind of started associating cooking dinners with, like, having more intentional time with my partner. And it's so fascinating how my whole mindset about cooking dinners, which before used to be like, I don't have time. I don't want to. I want to outsource it. Why must I eat? Like, these were the thoughts that I had. But then, like, once I attached it to more value than just, like, I need to nourish myself. But, like, it's really like, oh, it's a pause, it's a break. I found myself really looking forward to the time that I could cook dinner. And we use gobble. So, you know, it's a meal delivery service pretty quick. It's very helpful. But I think that one of just no longer seems like something that I have to balance or stress to do. It seems like something that I want to do, I look forward to do, and I'm grateful to do. And so I think that has given me some rest and some pause and so just trying to do that with some other things, like how can I feel grateful about these things that previously annoyed me that also give me restrictions? So.

Yeah, so I love that idea of like making that dinner, like the ritual part of it and you know, kind of making it that ritual to like end your day or at least take a break and have that time with your partner and just. Yeah, I, I think that's such a great point. I mean, I guess I kind of use dinner that way to connect with my kids and my husband also.

Yeah.

Even though I haven't really gotten to the enjoyment of cooking, I used to really enjoy cooking until had kids and now they don't like anything I cook, so it's not really that fun.

Well, I will say, I mean, gobble, it takes me like 20 minutes to cook and I think that's really important to this whole situation.

That's great. I'm gonna try it out though. We did hellofresh for a while and it was okay, but it took like an hour, an hour and a half to make the food. I don't know if I'm just really slow or what, but I just could.

Never make no gobble is like specifically faster. Like that's how I. Why I chose them. I think it's like everything has to be under half an hour. So I mean, because they, they do some things for you. So you're, you're not really cool thing.

That's nice.

Very cool. Yeah.

So I think another really great, some really great growth that I've seen from you is putting together a team, a good team. I mean, you've gone through lots of iterations of team and I know that's been a huge learning curve for you and you can't even like go to school, I don't think, for learning how to hire people. So maybe talk about that a little bit. Like what you have learned about hiring and putting together a great team, where to start.

Right, right, right, right. I feel like I'm always hiring also. So I do a lot of my hiring off of LinkedIn and I can't say enough good things about it. I also am a big fan of video interviews. So the way that I use hiring is I do LinkedIn and I'll do some pre screening questions and then the people that answer on the pre screening questions, usually I move them to a video interview and then from the video interview there's a zoom interview. I will say I got significantly better at hiring when I wasn't the only person hiring, which I know is not always feasible when you're thinking about your first hires. Yeah, but I now like, I, we're hiring for law school consultant and I bring in our director of pre law programming and our director of operations. And so we can kind of, there's a little bit more consensus. And even when we were hired our director of operations, I brought in my director of pre law programming for outline, I bring in our chief operating officer and sometimes our chief technology officer depending on the role. So there's always more than just me making the touch points and I think that's really helpful. That's been really helpful for me lately. But when it was just myself, I learned something. So first off, I learned that it's really important to just let people know what they're walking into. And I just don't think I did that at first. But I started being like, this is a startup. Let me explain to you what that means. It means you are hired. You know, you're interviewing for this role, but some days you may be needing to wear this role or that role. And like I remember when I hired, she wasn't a long term hire but she came in as like a project manager for the consulting side. And I, I was just so frank. I was like, listen, right now my goal is firefighting. There are many, many fires. And if you come and join our team, which I hope you do, you will also be engaged in the art of firefighting. And I don't know where the fires are coming from and I don't know when they're coming, but there's many of them and I, that's what we need. And that sounds like weird to say in an interview, but I would so much rather someone be like, you know what I'm for a very simple 9 to 5. And this does not seem like that. So we're not a good fit then to join. I mean they're going to find out what kind of place this is real quick. When we're in that kind of rapid growth, like nothing is stable, like really everything is everywhere. And you kind of just like that's just not for everyone. And you want with your early hires to find people who are going to be super dedicated to the mission and the vision that you have and want you to win. Like we just hired or we were interviewing a woman and I loved what she had said. I'd asked her about team and team culture, which I think people should ask more about too. And she said the mission that you have is too important. You can't fail. And if I were to join a team. My goal is to make sure that you don't fail because there's so many students that need what you're doing. This is too important of a business for us to let it fail. And I feel like that's what you need on your team. Like, yeah, they've got roles, but whatever it is, your business is, like, you need people that are like this thing. I have now some ownership over it and I am committed to helping you to helping it. Like, you don't. Like, when you're just hiring and you're new, like, you don't want workers like you. You don't really need employees. Like, employees. That's what they are, obviously. But, like, this is not like a punch in, punch out situation. This is like, you know, and I believe in a work life balance, but also, like, you need someone that cares, like it's your baby, like they're becoming a godparents. That's. That's the mentality that you need someone to take when you're just hiring.

And so you're pretty happy with your team now. Like, you feel like you've found a lot of those kind of people to bring in.

Yeah, I mean, we're still, you know, growing here. They're still filling some roles here or there, but I'm really happy with the core team for both companies for sure. That's awesome. I love it. Yeah. And the thing is, I, I, like, learn from them. I also learned to hire for things that I'm not good at. Like, and even just like, not just. I think people think of that and they're like, oh, I'm not good at paperwork. So I'll hire someone that's good at paperwork. But I think it's even like I have adhd and I like to think of myself as an organized person, but actually hiring someone that really likes spreadsheets and data and that, like, that's helpful. Or even hiring, like, for more experience, I think that's something that I had to grow past too. I am young and in consulting with younger students, I felt like it was really important to have a young team. No shade to the people that are my age. But like, also, it's totally fine to have people that are like 20, 30 years your senior because they bring a level of experience and expertise that's complementary. And it, it's great. Like, I, I am going to soon be one of the youngest people at my own company. And I love it. I'm here for it. That's awesome. I love it.

Yeah, Very good. So so what's next? Like what is the next chapter?

I think that both companies are in similar but exciting places. A little different. I mean they're different, but I think funding is really big for me in 2023. Funding and rest. So for Barrier breakers we've made that nonprofit switch. We have a sliding scale for our services and it's really about, I mean they're both still in growth and build periods. It's really about getting funding so that we can continue to grow. We have the second annual Break into Law conference this summer. It's a free virtual conference July 8th and 9th and there's a law school fair for prospective law school students. There's also a law firm there for those that are already in law school or even young practicing attorneys who want to meet top firms. And we have a resource fair. And so just getting more established I guess is the word. Right. And so getting a good donor base, getting good corporate sponsorships and partnerships and starting to become a little bit well oiled. Starting to find that rhythm. And I would say something similar for outline, closing the round is of utmost importance to me. It will hopefully be closed in the next 30 days though. So I'm pretty excited about that. We are named one of the top 200 pre Series A ed tech companies in the world. So we're going to the GSB cup next month. But for me it's really again about establishment. It's about getting the software into schools, middle schools, high schools, getting teachers using it, getting that brand name and brand awareness out and again becoming a little bit of that well oiled machine. I love it. Awesome.

And I wouldn't be a responsible board member if I didn't make an appeal. If you would like to help support Barrier breakers and creating greater access to law school for first generation and bipoc students, we would love to invite you to support Barrier breakers and the work that Sydney's doing. And how can we tell the audience how we can keep track of you and watch your progress and take in all the inspirational growth that I know is coming for you.

Thank you. Absolutely. So Barrier breakers. You can definitely find us barrier-breakers.org and you can learn about organization. You can donate, you can sponsor a law school student which would mean so much them. So there's definitely ways to get involved there. You can also find out about the conference on the podcast. Please definitely follow us at We Are Barrier breakers or at Break Into Law School or at S. Montgomery Consulting. You can also follow me at Underscore Sidney A. Montgomery. You can visit my website@sydneyamontgomery.com you can see things about Outline. You can see about the work that I've done. I have a couple of articles now that are out at Forbes and Fast Company and Medium and cnbc. So definitely I talk a lot about equity and education as a whole. So I would love to have you follow me. You can even follow me at Twitter at Underscore. Sid amontgomery. And yeah, I always appreciate the support. Yeah.

Well, thank you so much. I'm so proud of you and I feel so honored to get to be part of your journey and work that we got to work together. And I'm definitely gonna be. We'll be keeping in touch and working together in the future. So thank you.

Absolutely. I cannot say enough good things and you're just such a blessing in my life, Melissa. You've changed my life for the better. I would not be here without you. So thank you. Thank you. Thank you for your support. And I'm so glad that we got to do this podcast interview. Me too.

Thank you so much for coming on.

You're welcome.

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