Boss Mode: Leveling Up Your Leadership as You Scale
- Stephanie Roulic
- 1 day ago
- 46 min read
Scaling a startup doesn’t just test your business model, it tests you as a leader. The skills that helped you build your company from the ground up aren’t always the ones that will carry it forward. As teams expand, decisions get more complex, and expectations rise, founders must evolve from doers to leaders - learning to communicate vision, delegate effectively, and build systems that empower others to excel.
Recorded live at Startup Boston Week 2025, this session dives into how founders can grow alongside their companies. From redefining your leadership style to balancing strategic focus with empathy, the conversation explores what it takes to transition from founder to executive and lead with confidence through each new phase of growth.
Featuring insights from:
Michael Kadish - Founder and CEO, Incentivize
Joe Alim - VP Product & Ops, Compt
Julie Meyer - Founder + Principal, Connection151
Theresa Tribble - Entrepreneur
5 Takeaways
1. Leadership Starts with Empathy, Always Assume Positive Intent
Theresa Tribble shared a personal story that reshaped how she leads: early in her career, she misjudged an underperforming team member, only to later learn the person was quietly caring for a terminally ill parent. It taught her that “no one shows up wanting to do a bad job.” Her takeaway: before assuming a performance issue, check in on the person first. Compassion and curiosity are foundational to leadership, especially in high-growth, high-stress environments.
2. If Everything Depends on You, You’re Doing It Wrong
Joe Alim admitted one of his biggest early mistakes was becoming the bottleneck. As a founder juggling product, customer success, and engineering, he realized that true leadership meant building autonomy into his team. “If you can’t take a week off without everything stopping,” he said, “you’re in too deep.” Empowering others to make decisions - even imperfect ones - frees you to focus on strategy and long-term growth.
3. Communicate with Care, Ask ‘How,’ Not ‘Why’
Michael Kadish highlighted how language shapes trust. He avoids starting tough conversations with “why,” which can sound accusatory (“Why did you do that?”), and instead reframes questions around “how” and “what” to keep dialogue open and constructive. As he put it, “We underestimate how judgmental we can sound, even when we don’t mean to.” Thoughtful communication turns conflict into collaboration.
4. Delegate Intentionally and Learn to Let Go
All three founders agreed that scaling requires a shift from doing to enabling. Joe described the discomfort of stepping back once his teams ran smoothly: “It got quiet, no one was asking me for input. It felt weird, but that’s when I realized I could finally be strategic.” Theresa added that regular “time audits” help identify when you’re operating below your highest value, and it might be time to delegate, automate, or hire support.
5. Growth Means Knowing When to Step Aside
Perhaps the most honest insight came when the panel discussed founder transitions. Kadish and Tribble both noted that not every founder is meant to lead forever - and that’s okay. “You might not be the person to take the company to IPO, and that’s fine,” said Kadish. Tribble added that understanding what lights you up helps determine when it’s time to evolve, exit, or redefine your role. Great leaders know their legacy and when to pass the torch
Key Quote Highlights
All five of these quotes are direct paraphrases or lightly cleaned for readability
“If you can’t take a week off without everything falling apart, you’re not leading, you’re hoarding control.” — Joe Alim, VP of Product & Ops, Compt
“No one shows up to work wanting to do a bad job. When performance dips, start with empathy, not assumptions.” — Theresa Tribble, Entrepreneur
“We underestimate how judgmental we can sound. Swap ‘why did you’ for ‘how did you,’ it changes the entire tone of a conversation.” — Michael Kadish, Founder & CEO, Incentivize
“When your team runs without you and it feels weird, that’s actually a sign of success. It means you’ve built something that scales.” — Joe Alim, VP of Product & Ops, Compt
“Growth isn’t just about scaling the company, it’s about scaling yourself. Sometimes that means stepping back so others can step up.” — Julie Meyer, Founder & Principal, Connection151
Parting Thoughts, Video & Transcript
The conversation drove home that scaling a company is really about scaling yourself. As founders grow into executives, the shift isn’t just operational, it’s emotional, relational, and deeply personal. The best leaders know when to push, when to listen, and when to let go. They build teams that run without them, cultures that thrive on trust, and systems that evolve with the business. As Boston’s startup ecosystem continues to expand, these lessons remind us that great companies don’t just grow fast, they grow intentionally, with leaders who are willing to keep learning right alongside their teams.
Full Transcript Below
Want to revisit a particular quote or share with a teammate? We’ve got you covered. Read the transcript here:
Julie Meyer
[ 00:01:26,960 ] Awesome. Thank you so much. Hi, everybody. I'm Julie Meyer. It's great to meet you all. Thank you so much for coming here and being here for our session, Boss Mode. Uh, leveling up your leadership as you scale, and I've had the absolute pleasure of getting to know Michael Teresa and Joe as we got ready for this panel today. Hopefully, it's going to be a lively discussion you're going to learn a lot about their backgrounds, a lot about their experience, and hopefully take away some nuggets that will help you as you level up your leadership and step into, whoa, is that now too loud? Step into Boss Mode. Cool. Okay. Before, as well, feeling out the technology. So before, let me just, I'll introduce myself, and I have a couple questions for you all, then the panel's going to introduce themselves. So as I mentioned, I'm Julie Meyer. I am currently the founder and principal at an organization called Connection 151, which is a go-to-market strategy and sales coaching business. But my background had been in starting specialized consulting firms. in the food space, in the leadership space, and in the mentoring space.
Julie Meyer
[ 00:02:29,990 ] And I'm also, I am a lecturer and adjunct over at Northeastern University in both undergrad and the MBA program.
Julie Meyer
[ 00:02:38,810 ] I love talking about all this kind of, everything related to this. Startups, leadership, growing your businesses, being successful, connecting with your most valuable customers, and making an impact. So before I introduce the panel, just quickly, just like a show of hands, like how many people here are actual bosses? How many people are leading teams? Okay. How many people are founders but not yet with a team?
Julie Meyer
[ 00:03:06,740 ] Okay. And how many people are none of the above?
Julie Meyer
[ 00:03:11,620 ] Okay, great. Awesome. That's great. That's helpful. So we do have a lot of current leaders. So as we're going through the panel, please feel free to have in the back of your head what kind of questions you may have for our panel. We'll have about 15 to 20 minutes at the end of the session.
Julie Meyer
[ 00:03:26,800 ] Without further ado, I will stop talking. So I'd love our panelists to introduce themselves, but a little fun question before you get into the nitty gritty is if you can have breakfast with one leader, alive or past, who would it be and what would be one question you would ask? So if you could answer the question and then go ahead and introduce yourself. And starting over there with you, Michael.
Michael Kadish
[ 00:03:53,090 ] Ooh, okay. I don't have any time to think about the answer to the question. I'm on the spot. It's a good leadership lesson in and of itself. You never know what's going to happen. You never know.
Michael Kadish
[ 00:04:04,149 ] I'm gonna go with Franklin Delano Roosevelt. And I guess the question that I would have is, that I could ask is, is this world the world that he envisioned coming out of World War II that we would all, that would exist? And how disappointed/ slash excited would he be by where we are today?
Julie Meyer
[ 00:04:37,270 ] Love it, love it. And then along those lines, tell us a little bit about yourself.
Michael Kadish
[ 00:04:41,270 ] Yeah, so I was a history major, undergrad, I'll start there. Thank you. I have a master's in public policy. My background is really starting from that kind of politics, policy, and communications. I started really becoming a quote-unquote boss when I ran a non-profit. in California that installed solar for low-income families and did job training to teach skills to people, workforce development program, placing people in the solar industry, people who were incarcerated, people coming out of the military from different backgrounds. and grew an organization from about a dozen people to nearly 40 people with hundreds of different trainees and coming through every year. I'm also a founder of a climate tech startup that connected consumers to incentives for electric vehicles and EV chargers that I recently did an asset sale of.
Michael Kadish
[ 00:05:42,830 ] And today I am doing consulting, advising startups and just thinking about these issues and how to move forward in today's world. So that's on my mind. And I'm really happy to be here and humbled to be really around so many people that are doing, taking leadership and trying to make it happen for themselves and for all of us. So thank you.
Julie Meyer
[ 00:06:07,430 ] Awesome. Awesome.
Theresa Tribble
[ 00:06:08,310 ] Thank you. All right, Teresa.
Theresa Tribble
[ 00:06:10,150 ] Hi, I'm Teresa Tribble. Who would I have breakfast with? I'm like sitting here thinking like FDR. You said something. I felt like if you could drop this mic, one should.
Theresa Tribble
[ 00:06:20,060 ] I'm gonna go with Madam C. J. Walker, who I think, as a Black woman, building a massive empire a long time ago, I'm like, I cannot imagine.
Theresa Tribble
[ 00:06:32,200 ] The things I could learn from talking to her and like hearing about her experience. I just, I was like sitting here, I was like, who would I really love to meet? And I think it would be her.
Theresa Tribble
[ 00:06:41,800 ] Oh, and who am I? I am a serial entrepreneur at this point. I've been in early stage companies for almost 20 years, largely in biotech, consumer health, etc. been either a founder or first 10 employees of companies that have grown very rapidly, probably most notably a company called Everly Well, which was on Shark Tank that is now, I guess, Lori's most valuable asset that she ever has invested in from that show. and grew in the context of this panel grew from, I was probably employee number 10 and one of the first executives and grew to 80, you know, 80 to 100 people and, you know, many multiples of revenue in a very, very short time frame, probably like six to nine months. So I think if we're thinking about scaling, but then also on the biotech side of the house, I've worked with deeply technical.
Theresa Tribble
[ 00:07:42,500 ] People as a non-technical founder and spend most of my time thinking about ways to try to help people live healthier, happier lives.
Julie Meyer
[ 00:07:51,000 ] Love it. I see impact weeding through and then over to you, Joe.
Joe Alim
[ 00:07:56,570 ] Yeah, so if I could have breakfast with someone, I've been recently reading Let My People Go Surfing by Patagonia's founder, Yvonne Chouinard. Hard to pronounce that one.
Joe Alim
[ 00:08:07,050 ] I would actually ask him about this whole concept of work-life balance that everyone's been debating about for the last few years. Like, you know, is that really a thing? And, like, you know, to build a huge successful kind of business like that but still have, you know, the title of your book be Let My People Go Surfing. Like, how did he balance that, like, you know, accountability work? Hard versus, you know, balance in life. And I'd love to hear the thoughts on that one.
Joe Alim
[ 00:08:29,600 ] A little bit about myself. So I started my first company while I was still at Northeastern. I studied mechanical engineering over there. And I had no idea what it meant to start a company. And I was actually started at Boston, one of the first kind of like... educational events that I went to 10 plus years ago now that really gave me a lot of knowledge. So a lot of appreciation to this kind of organization and this community.
Joe Alim
[ 00:08:53,810 ] I ran that company for about five years. It was in the talent acquisition recruiting space. And now I've been at my current company Compt for about another five years where I lead product customer success engineering and I wear a lot of hats. So we've gone from about five ish to about 25 kind of fluctuating up and down a bit. and working with all sorts of teams, sales, marketing, customer success, engineering, and it's been a good time. So flexing in a lot of different areas has been a good journey. Excited to share with you guys.
Julie Meyer
[ 00:09:23,250 ] Love it. Love it. And you can see, I love that we have like a variety of different experiences from, you know, hundreds of employees working out and about to being in the first 10 to being on small teams.
Julie Meyer
[ 00:09:34,900 ] So I think we'll have hopefully something that resonates with everybody here. But let's start with the fun stuff. Let's start with what mistakes we made. Let's start with, so we started with breakfast. We're going to go into mistakes. Then we'll go into some big picture things. But, you know, I know, I mean, I could probably. give you a list of quite a few uh sometimes we feel like when we make mistakes it's like oh my god the most tragic thing that's happened but that's of course how we learned and how we grow so what are mistakes that you made early on as a founder or leader and what were some of the best lessons that you had over time and i will start to keep circulating around i'll start with you theresa so michael doesn't have to get right in the hot seat okay again um and then we'll go with joe and then michael's yeah so if i think about it in the context the mis i mean i've made so many mistakes but um and uh you know, if you're not making mistakes, you're probably not taking big enough risks.
Theresa Tribble
[ 00:10:27,800 ] But the, I would say in the context of people and leading a team, some of the biggest mistake.
Theresa Tribble
[ 00:10:36,180 ] That I ever made, I think, was actually when I was in consulting. I was probably, you know, around 25, and I was leading my first team. There was a person on my team who was just not pulling their weight at all. And I created a whole narrative about how this person just didn't care and this and that. And it turned out, of course, that this person's dad, you know, I find out after the project's over, after it's been terrible.
Theresa Tribble
[ 00:11:08,080 ] I find out this person's dad was dying of lung cancer. And she never told me. She never disclosed anything. She never told anyone in the firm. And it has always colored my leadership style and my management sense, where it's like, no one wants to do a bad job. I don't think anyone shows up on any given day and is like, 'Yeah, I actually don't want to do a good job.' So I think coming in to any time someone's underperforming and really being like, 'Hey, what's going on with you as a human first and figuring out if there's something there that—'
Theresa Tribble
[ 00:11:38,690 ] is would be completely explain why someone's distracted or underperforming or leaving early or coming in late or whatever. For me, I think that's the one that I carry and try to use that.
Julie Meyer
[ 00:11:50,369 ] Yeah, yeah, it is really hard to be in that position. It's harder than anybody would think. That's great. Thank you for that. Joe, what about you?
Joe Alim
[ 00:11:57,750 ] Yeah, I think this is a mistake that I kept making repeatedly in my earlier career, which is really just being the bottleneck for so many parts of the organization. I think especially when you're first starting out and you have to, you are the only person to do everything, it's really easy to keep that attachment as you start to grow and scale your business. Like even right now, you know overseeing three departments formally and some other functions, you know informally There's a lot of stuff where I for some reason keep finding myself like people asking me to be like the final decision maker on And I think what I've learned is like in order to truly be able to scale your own capacity and the business and kind of grow and hire, and then have people who can kind of step up in the future, you need to. give people more autonomy. And not everything's going to be done, you know, your way or the way you thought it was going to be done. Communication and, you know, boundaries and guardrails and guidance is really important.
Joe Alim
[ 00:12:58,400 ] Coaching is important. But if you find yourself finding yourself in a trap where, like, it seems like everything just, I'm blocked on everything. And if I take a day off or a week off, it's like everything stops. It's kind of you're in too deep at that point. You kind of need to take a step back and reevaluate. So I've learned a lot. I still think it's my tendency because I think I'm very much someone who likes to do things themselves. But knowing that this is something that I'm prone to allows me to continuously reflect on that and go, 'OK, do I really need to be a decision maker on this? No. OK, let's. You know, Mary will own this, Francisco will own this, like someone will own this. And I think that was a big learning, especially in my early career.
Julie Meyer
[ 00:13:37,700 ] And you may have been in a situation with Teresa's where they're kind of shutting down, where people are shutting down, they're not doing their best work. And asking those questions with empathy allows you to even— you know—consider things going on in the personal life, but they could be feeling, you know, something's preventing them from being able to step into that role as well. So communication sounds like it's a big part of it. Michael.
Michael Kadish
[ 00:13:55,940 ] Yeah, I mean, I wanted to just build a little bit on what Teresa said. How many people have heard the axiom 'slow to hire, quick to fire'?
Michael Kadish
[ 00:14:04,560 ] Right. So, you know, there is obviously truth in it because it's a cliché, but I do think it's obviously the truth is more subtle, right?
Michael Kadish
[ 00:14:13,310 ] think that's a really good example of where better communication right would have done it on the other hand sometimes there's a thing where like i personally when i started was a really soft soft touch like i loved uh i loved like a like a heartache story from someone and You know, your dog died six times this week.
Michael Kadish
[ 00:14:36,810 ] but i think you have to be able to start to distinguish between what's kind of a legitimate thing in someone's life that they like a challenge for them to get over that maybe you can help them and you can provide the patience in the sounding board versus people that are turning your culture toxic There are those people. We don't really want to talk about it because we want to think that everyone is wonderful, but we've often all been in the workplace with somebody, right? That's the person who's always talking smack, who's saying they didn't like this or that.
Michael Kadish
[ 00:15:08,840 ] Those are the people, especially I think, when you're creating a culture, that are really going to be damaging to you as you go forward. And then, just another quick thing I'd say, which is, I'm also, as a non-technical founder, often, especially at a smaller startup, product kind of leads and you end up, I mean, this is like a classic also trap. The product people are always like, let's just make it better. If we only made it better, if it was just better, let's just also, again, try to make it better. And you're like, it's totally a mistake. I, in my judgment, having never done that. Yeah.
Michael Kadish
[ 00:15:48,679 ] What you need is product market fit. And once you have something, then you can iterate on it and make it better. But if you just sort of defer to them and it's true, like it can always be better, you know, like it can always be better, but we all know there are lots of examples of businesses that aren't— they do not have the best product, but they dominate the market. So, that's just something else I'd throw out there is like not putting product totally paramount over everything. PMF matters a lot.
Julie Meyer
[ 00:16:21,620 ] especially if you're a product leader, if you're a product-driven founder. At the end of the day, it's really important to think about the sustainability of the organization, not just the sustainability of your idea of the product and how do you create a sustainable organization for everybody. Well, that's actually a good segue. We're going to talk a little bit about technical founders, since I know we probably have quite a few of those here. And I know, Teresa, you were talking a little bit about your experience coming in. working with technical teams. I don't know if you have not necessarily been the technical founder, but you've come in in the very early stages. Any particular advice on those either as technical founders who are starting to build a team and or those coming in as leaders with technical founders?
Theresa Tribble
[ 00:17:07,560 ] Joe, do you want to go first since you are the technical founder and then I am the non-technical founder who brings the technical people?
Joe Alim
[ 00:17:14,880 ] We can do a little point counterpoint. I'm kind of in between. So I studied mechanical engineering and I have a master's in engineering management. So for a while I was more on the technical side, but as soon as I switched to dedicated and software, I don't know how to write code. So I've been kind of straddling between the two, and I think that's actually where I shine.
Joe Alim
[ 00:17:35,650 ] My general thought, and I'm going to, you know, my best friend, I'm the godfather to his daughter. Like, he's also still my head of engineering. He was my previous co-founder. So I'll just say it, you know, out loud. His name is Francisco. Francisco is he— is like the best technical engineer, you know, I've ever worked with. He's so brilliant. He's so smart. And some of our greatest frustrations with each other was when I was trying to push the business agenda and he was trying to push the technical agenda. And I think earlier in our working relationship.
Joe Alim
[ 00:18:07,970 ] Like me, basically, kind of shutting his technical side down, like that doesn't matter, the tech that doesn't matter, like scalability and security don't matter. We just need to close deals. We need sales in order to have the company survive. That can make someone really shut down and get them demotivated. So I think that's like one thing to really be conscious of, especially if you're more on the go to market side. Like you might know that, hey, we have six months of runway. And if we don't close these investors or these deals, our company's dead. So I don't care about technical debt that's going to hit us in a year or two. That being said, you can't steamroll your technical folks like that because, at the end of the day, that's like also the lifeblood of your company. So I'll say from kind of that perspective, it's like making sure your engineers—regardless of their role— really, really feel heard, no matter like. what state the business is in. And the one other kind of nuance is: don't think that technical folks don't have good insights and opinions about the business side as well.
Joe Alim
[ 00:19:11,040 ] They are very smart people. Don't dismiss them there. So I'd say those are a couple of points that come to mind.
Theresa Tribble
[ 00:19:18,330 ] Yeah, so I am not a technical founder. I was an English major and I have an MBA. But I have worked really hard to be, I don't know, fluent in the technologies that I am developing.
Theresa Tribble
[ 00:19:38,160 ] So I'm often confused as someone who has a PhD or something like that because I will read all the scientific papers required. And so most recently, I was the co-founder and CEO of a company called Droplet Biosciences, which is located in Cambridge. And is using lymphatic fluid as a source of biomarker information to improve cancer patient care. And I co-founded that company with one of the leading head and neck surgeons in the US.
Theresa Tribble
[ 00:20:06,560 ] A guy that I describe as a radiation oncologist by day and a genomics pioneer by night, because he spans a very broad gamut of, you know, great clinical medicine to machine learning and things like that.
Theresa Tribble
[ 00:20:21,080 ] The way that I proceed with on a co-founder level is asking a lot of questions. And sometimes by asking questions, you can start to demonstrate that you're bringing a different type of expertise to the table and you allow others to share their expertise. I think.
Theresa Tribble
[ 00:20:40,790 ] The types of companies that I like to build tend to be somewhat technical, but we never lose sight of 'so what.' And so that's what I think I uniquely bring to those groups is understanding why the technology matters, but also—why do we care for normal people? What are they going to get out of it? And sometimes that can be difficult, I think, as Joe's saying, because you're like, 'Hey, it doesn't actually have to be 100% perfect for it to really profoundly improve people's lives or the care they might be receiving.'
Theresa Tribble
[ 00:21:11,980 ] I think the other thing that I've learned, I think particularly working with my last CSO, we would have these moments where I'm a highly intuitive person. And so I would like see something, we'd be having a conversation, I'd be like, 'Oh, I'd get it.' And then I would make some sort of six-level leap to some other place.
Theresa Tribble
[ 00:21:31,690 ] And she's like, 'I love you, but you've got to stop doing that.' You need to, like, help me, like, you need to articulate the five thoughts that must have just gone through your head that you've just assessed and made some sort of plan. She'd be like, 'You're not thinking it through.' And I'm like, 'Oh no, but I thought it through, right?' And so I think thinking more like the way that the people that I worked with were trained and how to communicate in an effective way with them can be really, really.
Theresa Tribble
[ 00:22:00,810 ] I think has been helpful, like having somebody as a partner alongside me, honest enough with me to be like, yeah, this isn't working for me because my brain works in a totally different way. And in order to come with you on this journey, I need you to adjust how you're communicating your vision.
Julie Meyer
[ 00:22:17,870 ] And sometimes it feels like that, like, sort of strengths finders work or some of these, like, leadership things. They're like, oh, of course, Nora. But it can be really valuable to bring in those experts who can really help provide that outside perspective and facilitate that communication so that you can sort of have that groundwork laid.
Theresa Tribble
[ 00:22:33,790 ] Yeah, we used Enneagram for that, which I think was actually pretty helpful.
Michael Kadish
[ 00:22:37,930 ] That's cool. I just have a very basic tip that I got from an investor that was a little bit of an aha moment for me, which is just if you're a single founder who's out there and you're non-technical, and you're going to create a product that has software, your technical founder has to code. That was the tip. Because otherwise, you're raising money just going out the door to pay somebody else to code. So your runway is totally shorter. So you really, if you're going to try to bootstrap it as a team, the two of you or whatever, you want to have the coding capacity in-house. Obviously, that's changing now. It makes it almost even easier to do that. But just as a short, I would highly recommend that.
Julie Meyer
[ 00:23:20,970 ] And then it really plugs you into both sides of the business, I think, as well, if you have somebody who's a founder with you in that space. This wasn't one of the sort of initial questions, but it kind of came up through everything that you all were discussing. I very much like focused on the words and the language and like the script. Are there words or phrases that you've used either with your founders or with your teams or with people when you're kind of you are you are seeing signs that you're approaching a difficult conversation or there has to be a moment where we can't just kind of keep pretending that everything's OK? Are there phrases or words that you typically use to get to where everybody is ready to have that conversation? I'm asking for a friend. Go ahead.
Michael Kadish
[ 00:24:02,900 ] I mean, I think one thing I learned that stuck in my head was that rather than asking why, which can often come off, I think, as like, why would you do that? And how many of us love getting that question?
Michael Kadish
[ 00:24:15,660 ] Even though that's what you're thinking in your head. You're like, why would you do that? How did you do that?
Michael Kadish
[ 00:24:22,610 ] And like, what is this? How? And kind of getting them to talk about it and just trying to be, I think.
Michael Kadish
[ 00:24:32,020 ] less, I guess we underestimate as leaders, sometimes like how judgmental we can come across when we're having those conversations. And so really being sensitive about that, like you want to talk about that issue.
Michael Kadish
[ 00:24:46,030 ] Absolutely, and you should be able to. But if you are sort of putting somebody on their back heels, it's not probably going to be the type of conversation and the type of follow-through that you'd like to see. So I think it's like being artful. Hey, how did you come up with that? I'd love to understand your thinking there. It's a lot better than...
Michael Kadish
[ 00:25:04,490 ] Why would that be the case?
Julie Meyer
[ 00:25:05,790 ] Yeah. Help me understand. What about you? Joe, you have anything?
Joe Alim
[ 00:25:08,030 ] I have a book that I would actually universally recommend to any earlier managers, but also more season one. It's called The Leader Lab, and it's by an organization called Life Labs, which is where I learned a lot of core.
Joe Alim
[ 00:25:25,870 ] Kind of manager skills, and there's a lot of things in the toolkit. Like it's really— I think, like, I gift this to anyone who's a relatively new manager, so Leader Lab. One of the things in particular in that book is just like it talks about playing things back to people. There's so many times where, like, frustration stems from just simple misunderstanding and miscommunication. And then the more heated things come, the more kind of tension. It's like the more you guys aren't, you know, you're not picking up what I'm putting down— like all this stuff. So, like, something that I just kind of have on repeat in my mind is like: if I'm understanding you correctly, you just told me X, Y, and Z. And then sometimes I go like, 'No, absolutely not. That is not what I meant.' And then you kind of, you know, you repeat, you get clarity. And I think it feels a little bit annoying at first to have to like constantly like rehash what somebody just told to you. But like, whatever you're hearing sometimes through your own filter, you might be processing differently. So especially for something more complex or nuanced or sensitive, I find that just like playing it back to the person is just super helpful.
Julie Meyer
[ 00:26:26,460 ] And Life Labs has great web free webinars. You have tons of free webinars and it's a great organization. Go ahead.
Theresa Tribble
[ 00:26:32,430 ] I think to build on that, some people really need to read things. And so not just rehashing things verbally, but also writing things down if you've had a conversation. And it can be. On a personal level, I mean, HR may tell you not to do that, sometimes depending on what it is. But if you're talking about strategy or performance or things like that, I think sometimes rehashing it in writing allows people to be like, 'Wait, I didn't quite read it that way.' Or they're like, 'Whoa, what is this thing?' So I think that can be helpful, too. I was going to suggest, you know, you made a suggestion, Joe, so I'm going to suggest Crucial Conversations, which is a very famous classic book about how to have tough conversations with people. But one of the things that I always, there's a song I'll sing with the team, which is kind of just like, 'This is why I love multifunctional teams.' Cross-functional teams are the best. And part of that is a lighthearted way of reminding everybody that we all come at our.
Theresa Tribble
[ 00:27:32,720 ] problems as a company from the training that we have and each person is bringing something important to the table. I work in very highly regulated industries. I do not have the right personality to be somebody that's going to make sure that our quality management system is going to get through the FDA, but you know what? If I do not have the kind of person that that lights up their day, who is excellent at their job, who may have a very different vibe from me. If they're not great at their job and not bringing that perspective and the parts of their personality that make them excellent at that, we're not going to get where we need to go. So I do that sometimes to remind myself, but also to remind the rest of the team, because you'll see those conflicts at intersections, marketing and sales.
Theresa Tribble
[ 00:28:14,240 ] All the natural places where there's tension, those tensions are natural, they're good, and you can work with them in a productive way.
Julie Meyer
[ 00:28:22,040 ] Having everybody and everything is perfect. Easy conversations just to your point. You know, if you haven't had made mistakes, you haven't really tried hard enough. So, if everybody, if every conversation is great and everybody's happy, you are dead. I think.
Theresa Tribble
[ 00:28:35,430 ] Also, yeah, I also think you know. Given that this is partially about as you scale, I think that you can people can understand your intent better when there are five of you around the table and you're brand new. As you continue to grow, you have to, one, do more things in writing. You actually have to communicate the thing that you're trying to communicate many, many times. It's just like you're effectively marketing to your organization if you're really trying to communicate the big ideas. And so you have to do the things over and over again. Get to a place where everybody can articulate like either what the North Star is or whatever it is that you're trying to get out there has to be done in a much more scalable way and it will be less personal to you and needs to be propagated through the org.
Julie Meyer
[ 00:29:21,540 ] And again, internal comms, like leadership training is like— oh God, we need like an internal, no, an internal, depending upon your size, an internal comms person is gonna save you a lot of money in the long run. So I have a question.
Julie Meyer
[ 00:29:33,600 ] So as founders, as you are identifying where you have actually kind of peaked in terms of your skill sets, like you have gotten as far as you can get with this particular area.
Julie Meyer
[ 00:29:46,680 ] How do you know when that happens? And how do you know when to bring in like the next rung of people?
Joe Alim
[ 00:29:53,590 ] do you have a moment or did you have a moment maybe you could describe where you were like okay i've now nailed this piece of the business i feel like i'm gonna start with you joe and now now i actually really need to either elevate myself to an executive level i need to really understand this other part of the business i need to shift my role Yeah, so when I first joined Compt, I led all of customer success and product and engineering also rolled up into me. I was the only person on the customer success side of the house. So every support ticket, every implementation, every customer question, all of that funneled into me. My first thing is I need to build out a team. I can't be answering like support tickets 24-7 because then I can't be strategic and kind of so on and so forth. So really my first, I'd say two and a half years at Comp was building out. a customer success team where my head of customer success now, her name is Mary, and then also bringing out the engineering side with Francisco, who's my head of engineering, to where they could operate almost autonomously with very little input from me on anything that was kind of like...
Joe Alim
[ 00:31:00,190 ] a day-to-day function if it was like hey critical customer issue or like you know there's an outage or like we're having trouble prioritizing yeah let's kind of bring that and let's have a discussion and like i it sounds like i'm kind of like trying to push them away almost but it's almost like i had to consciously be like no, you don't actually have to ask me for input here. No, don't ask me for input here. And I have to keep saying that over and over again. And I think around late 23, probably, I reached a point where I'm like, huh. no one's asking me for anything on this kind of day-to-day basis thing. I was like, it's kind of quiet around here. And I remember saying to my CEO, is there other stuff you want me to tackle? She's like, you know what? That's a really good time. Now you can be a lot more strategic. You can think about. You know, our next round of funding or our exit strategy— think about our partnerships. Like, she's like, you know, it wasn't like a good or bad thing, just timing. But she's like, you're now at the point where you can really zoom out. At first, it felt uncomfortable. I felt like very detached from like the day-to-day stuff of the business.
Joe Alim
[ 00:32:03,250 ] But, like, over these last kind of year and a half, two years now, I'm just like, 'Wow, I'm making impact in so many different ways.' Because I'm not like, 'Oh, this customer's renewal date is next week. How's that gonna go?' Or, like, this feature's design looks kind of, like, is this the right blue? Like, I don't have— I shouldn't think about that anymore. And part of it feels weird because I grew up, my parents owned a deli in New York City. And there was no job beneath us, right? That was what I was taught. Like, you clean the floors, you throw out the garbage, you do all this. That was so instilled into me at an early age. I'm like, 'I was still like two years ago, I wanted to jump in on support tickets, but like, I had to kind of let all of these things go so that I can be like, oh, like the day-to-day stuff is settled.' And I think that was like a very definitive moment for me. So it does happen. It's huge.
Julie Meyer
[ 00:32:53,380 ] You're seeing a keyboard cat, right? The keyboard cat is just like going like this. And it's like, OK, eventually you have to stop. Just do it. Go ahead.
Michael Kadish
[ 00:33:01,100 ] yeah i guess i would just say sometimes you you have a you kind of start something and you're like i want to achieve x y and z and then you kind of get there and now you sort of are like okay now i'm just we're just kind of fulfilling the thing. Right. And maybe for, at least for my personality, then it starts to get a little boring at that point. And so sometimes you, you just are like, great like like like these things happen we're now at this place maybe i'm not really an ops guy i'm more of like a vision guy and it's time for me to go because i think this is like i fulfilled that and that's okay you don't have to stay at the same place forever trying to twist it into whatever is your, you know, vision of the moment. Uh, it's, it's okay. And I think if you've done a good job, if to Joe's point, you're like, you've trained people up, they've filled those roles and they frankly don't even really need you to do it. I mean, there are people I started working with who had like let's say, never done a government meeting, years later, they're applying for grants, they're getting millions of dollars, they're building programs, like nationally, they're doing all this stuff, and it's like, they're better at it than I
Michael Kadish
[ 00:34:15,389 ] think I am now, because they had the sort of, you gave them the exposure, then there's the delegation.
Michael Kadish
[ 00:34:24,219 ] There's a sort of phase where you're doing it together. And then there's the phase where you're like.
Michael Kadish
[ 00:34:28,760 ] great, I'm here if you need me. And then there's a phase where you're like, you really don't need me. I'm going to move on to the next challenge. And they tell you to go away. Yeah, that's when you go away. But it's sort of like, I think it's, I forget what the pithy phrase is, but it's sort of like, if you do it right, you kind of work yourself out of the job. Yeah.
Theresa Tribble
[ 00:34:46,560 ] Teresa, anything to add there? I would say that that makes a ton of sense. If we're thinking about when to shed responsibilities.
Theresa Tribble
[ 00:34:55,120 ] I tend to do these time audits like once a quarter. This makes it sound like I'm way more formulaic and organized than I actually am, but I'll get to a point often where I'm doing things and I'm like, wait a minute, how am I actually spending my time this week? And is that helping me fulfill what I view as a founding CEO as sort of the three things I'm supposed to do, which is set the vision, build the team, and fund the business? Because I'm typically doing things that require a lot of venture capital.
Theresa Tribble
[ 00:35:24,510 ] I will do that. And then I strongly recommend finding yourself an executive assistant who, even if it's like first at 10 hours a week, who has no filter to be like. You should not be running payroll. You should not be doing, you know, what are the, all the, you know, the things that we, yeah, like you shouldn't be booking your own hotels and you shouldn't be looking up the email addresses or, you know, the LinkedIn profiles of the people you're going to meet for the next three weeks or whatever it is. But there are so many things that you do because you're like, it just takes a minute. that actually can take you away from making the business as successful as it can be. So I think keep that in the back of your mind like every so often, just take a step back, look at your calendar if you use them.
Theresa Tribble
[ 00:36:04,950 ] and be like, what did I actually, like, what am I actually spending my time on? And is that the highest and best use of me? I think that's one thing. I think the other is, I mean, when you're thinking about, you're bumping up against your own limitations as a leader.
Theresa Tribble
[ 00:36:19,850 ] have had the best CEOs I've worked for have all had great executive coaches. I have a great executive coach who I think, you know, we haven't talked about, you know, being a founder, even if you have co-founders, can be very lonely, particularly if you've taken the CEO seat. And you're now effectively managing your co-founders. And so you have a board. You may have investors. And I think that that is a place where finding either a CEO peer group that you can work with, which I also have and recommend, where we meet once a month for a few hours and sort of. Know share challenges and opportunities and growth and learnings, but also having an executive coach like you— know the best people know that they need support and so don't view it as a shortcoming; it's really an opportunity for you to rise to the next level.
Julie Meyer
[ 00:37:10,580 ] I love that. I love that. Actually, I was going to ask you, Michael, Joe, what resources you have. I know you mentioned some books and you mentioned, you know, kind of peer groups as well as coaches. And I love that idea of like, who's reflecting to you— like it's time for you to move on. Like, who do you kind of surround yourself with? Is there any other?
Michael Kadish
[ 00:37:25,050 ] No, I mean, I think those were great points. Having some time management candor from somebody on your team is great. I really do think that, however, you can get a peer group of people, it is lonely to be the boss.
Michael Kadish
[ 00:37:42,399 ] Nobody cares, you know, because of the way it is. People aren't like, 'oh, the boss is having a tough day,' you know?
Michael Kadish
[ 00:37:48,180 ] Like you, and you're not gonna, you have to be strategic about, you're not gonna vent to your board members. They might say to you, like, 'come tell me like how, you know, like I'm here for you,' but like.
Michael Kadish
[ 00:38:00,040 ] Quickly, you'd be like, 'okay, maybe that's not, no, no, no.' Like, I shouldn't talk to him about that. And you really want to be in a peer group or with a coach. I think the peer group thing is awesome because. You get to say, 'Hey, I have this problem. Have you ever experienced this problem?' And they're like, 'Yep, this is how I did it' or 'This is my thoughts—I think that's just so critical for getting strategic help, tactical help, and also, like, that feeling of 'I'm not this weird, you know? One person with the world on my shoulders.' I'm actually just, there's lots of other people in the same position as me.
Julie Meyer
[ 00:38:40,500 ] And it helps, I think, to also share your experience with somebody that feels good for you, too. You know, I think just being of service to other people is helpful, too, in those kind of conversations, like being able to share that. What about you?
Joe Alim
[ 00:38:50,450 ] I'll add just one quick thing. I don't know what everyone's financial situation is. When I was graduating and starting my own company, a coach, any paid community, that was out of the question. Even a few months ago, someone was like, 'Hey, you want to join this super special executive community?' It only costs $12,000 a year. And I'm like, 'Nope. I'm not interested in that right now.' I got daycare bills. I got all this stuff. What I found super helpful early on is Slack communities. There are so many Slack communities for very different niche areas. like there was a customer success leaders one that i joined early on there's um i'm a big fan of lenny's podcast and newsletter on the product and growth side um there's occasional meetups on that one there was like an hr community like boston people ops people or something like that And like all these little communities have their own little virtual or in-person meetups that like you start to build your own pockets of like, hey, for like product stuff, I go here for engineering stuff, I go here. So like that's like a really good, mostly free way to like establish a sense of community when you're like the only functional person in a certain area.
Joe Alim
[ 00:39:56,180 ] um and then like definitely look at like things like eventbrite meetup luma um for like what's around boston i think the we're just chatting about this like the boston tech ecosystem i would actually say was a lot more busy with tons of events pre-pandemic But I think we're having a comeback. Things like this are, you know, really important. Like, look out there for events that are like, and even if you're nervous, you know, like, I don't know if I'd fit in here. Just go. Like, people who go to events are there to meet people. Like, so don't, like, hold yourself back and be like, oh, like, I'm an early founder. Like, maybe I'm not at the same level as them. Just go. Like, you'll usually build some really good connections and at least have good conversations. So, yeah.
Theresa Tribble
[ 00:40:35,540 ] That's awesome. Go ahead. My CEO peer group is free, by the way. Okay, okay. Let me tell you how it came together so that you can think about it for yourself. So someone, I was on the board of a company, the chief commercial officer left. And he became a CEO for the first time. I then left and became a CEO, like really for the first time. And he was like, 'I'm gonna put together a group of people. I'm gonna invite eight people that I know who are in the same boat and see if they wanna get together on Friday mornings.'
Theresa Tribble
[ 00:41:08,230 ] It's been amazing. So like you can do this, you know, if you go to the events and you do the things and you meet some people who are either in your function or also founders or whatever, and they resonate with you.
Theresa Tribble
[ 00:41:21,160 ] be like hey do you want to get on zoom or meet in person you know for an hour and see what happens we've been doing it for two years and it's like i do not miss that meeting Well, the good news is the session ends at 3 .
Julie Meyer
[ 00:41:33,105 ] 30. And there will be, if you want to meet, go on over there in the corner. I'm just kidding. But if you want to go in the corner, it's like we have a lot of group of people here who are probably all in similar boats. So if you want to get together, this is exactly the best kind of event to do this in. So I think we'll go ahead and open it up to questions. since I imagine I'm gonna defer to these folks. If you have a question, please raise your hand. There's one in the back over there. Jeremy, behind you, over there. There's somebody. Yep.
SPEAKER_6
[ 00:42:00,960 ] Hi, guys. Hi. Sagar. I run 4Fish. I have a question, actually, for a friend of mine who's not attending the event. They wanted me to ask.
SPEAKER_6
[ 00:42:12,000 ] One thing about scaling and one thing about growing with leadership is preparing for the eventuality. If you can't grow well enough, you'll get replaced. Do you have any advice for them?
Julie Meyer
[ 00:42:25,720 ] You can't grow as a leader or that the organization will go away?
SPEAKER_6
[ 00:42:31,480 ] As in like you might be replaced as the CEO, as the leader of the company based off the investors or stuff like that. Got it.
Julie Meyer
[ 00:42:40,880 ] You might not be the right person to take to the next level. Yes.
Julie Meyer
[ 00:42:45,040 ] Does anybody have experience or thoughts on that?
Theresa Tribble
[ 00:42:48,400 ] No, go ahead. I'll go after you.
Michael Kadish
[ 00:42:51,120 ] I mean, I think there's a, this is almost like, I mean, I don't really exactly know how to answer this because it feels a little bit like very specific to the situation and to the person, right? It's kind of like. Sometimes you reach a point where you're like, all good things come to an end. Like this, it's time to leave, right? Like we all.
Michael Kadish
[ 00:43:12,600 ] I don't know, we all, but it's Boston. Like most of us are sports fans, right? And it's like, you don't expect the person to be in the same thing, doing the same thing forever. There's a time where you realize, like, maybe you're not, maybe things have changed. You've changed and things have changed. So I think there's just some personal work about accepting that.
Michael Kadish
[ 00:43:29,280 ] But, you know.
Michael Kadish
[ 00:43:32,650 ] If you, if it gets to having an honest appraisal, talking to people that you trust, talking to your colleagues, talking to your board. And, and I think it's okay. Like, the thing is, is like, you don't have a.
Michael Kadish
[ 00:43:45,520 ] Even if you're the founder of something, if you get it to a certain point, you really might not be the right person to be the leader at that point. And that's probably okay. It's one thing to found a company and scale it to a certain point. You might not be the person to take it to an IPO. You might not be the person to lead it after an IPO.
Michael Kadish
[ 00:44:06,120 ] And that's totally okay. I mean, I feel like you've seen this more up close.
Theresa Tribble
[ 00:44:10,680 ] Yeah, I mean, I...
Theresa Tribble
[ 00:44:13,690 ] There's a point, and I think if your friend were here, what I would say is I'd be like, 'What do you like doing the most?' And you may find, and I have found, that there is a point where the things I need to do, the majority of what I need to do on a daily basis isn't actually what lights me up. isn't what I think uniquely I bring to any situation that I'm in. So there's a point, and I think you only realize this after you get over your ski tips or whatever the saying is. And you've gone past that point. And so for me, like when I was at Everly Well, I mean, we were growing so fast. That company was based in Texas. I was here.
Theresa Tribble
[ 00:44:52,440 ] I basically succeeded myself out of a job in the sense that I had to leave because I was on the road 90% of the time. And I couldn't move to Texas for personal reasons. And I was like, I can't do this anymore. But also, I figured out how to sell the product. I've done the first deals, all the B2B. I've landed us in Target and CVS. And I did these deals with these big insurance companies. And now it's just rinse and repeat.
Theresa Tribble
[ 00:45:19,100 ] and it's boring. So for me personally, other people would love it. So I think that's one thing. But I think anyone who particularly has taken outside investment and has a board.
Theresa Tribble
[ 00:45:36,150 ] I always tell people, look, there's really only a couple ways as a CEO that you leave your role. You can choose to leave because you're like, ah, I want to go do something else. But most of the time, you're probably going to get asked to leave. And you just have to be prepared for that. Most people don't make the whole, don't run the whole race.
Julie Meyer
[ 00:45:54,320 ] There's a word that I've been working with a lot and talking about— resources. One of the best leadership books I read, especially for new leaders, is called The Unexpected Leader by Jacqueline M. Baker, who is somebody that I work with. And we're really working on normalizing the word legacy. And so helping leaders to identify their legacy when they start, what do they want to leave here? What is the legacy of them in this organization? And then helping them when it's time to get started thinking about like, okay, you know, now it's, I left my organization that I had founded after 13 years and, you know, grew to eight figures and it was great. And it was like, okay, what's the legacy I'm leaving? I've done everything I can do. um so really planting that seed and even ourselves as leaders reflecting on what kind of legacy do we want to have at this organization and then what kind of legacy do we want to leave in the world after this because you know our jobs are great our companies are great but there's more that we can do i'm starting to help people really see that And just normalizing that kind of conversation, I think, is my two cents. Anything you want to add?
Julie Meyer
[ 00:46:55,020 ] No, I'm staying in my company forever and my current role and everything.
Joe Alim
[ 00:46:58,040 ] No one's kicking me out.
Theresa Tribble
[ 00:47:00,960 ] It's okay, Joe. You can call us when you need to. Yeah, thank you.
Julie Meyer
[ 00:47:03,740 ] We'll come up with something good for you to do. We'll go back to the deli. Don't worry. There's always going to be need for that. AI won't replace that. Okay, in the back.
SPEAKER_2
[ 00:47:10,990 ] Hi. Thank you so much for the talk. Joe, I really resonated with what you're saying about no task beneath you and having that work ethic. As a startup founder myself for a tech company called PriorWise, I sometimes do struggle with that.
SPEAKER_2
[ 00:47:26,010 ] the way i justify it is like you know by doing it myself i'm not only like uh you know saving the company some money but also you know like uh this is what i gotta do so i how do you make the decision from like trying to do everything yourself uh versus you know, as scaling, like hiding someone else to do it or delegating it to someone else, like how do you make that trade off? I'm curious to hear your thoughts on that.
Joe Alim
[ 00:47:50,630 ] I'll use like very specific examples. So I don't write code and I'm not a product designer by kind of trade or education or anything like that. Early days when I was designing— kind of like our web app— I was legitimately using Google Slides to mock up websites because I didn't know how to use Figma or Illustrator or all these different tools. And I just kept punting on hiring a dedicated designer because I was like, 'I'm getting the job done. It's good enough. Like I'll just— I'm saving the company, you know, 120 grand to not hire a dedicated product designer. And I realized that it was taking me so long to get like these prototypes done because I wasn't the right one. experience for it and then i was like now i'm kind of dropping the ball on some of these go-to-market responsibilities now i'm kind of like not really using my strengths as like a product leader and a go-to-market person because I just spent six hours trying to move boxes around on Google Slides. So I think when you're running into a point where you're like, this is actually not a strength of mine, and I actually don't want it to be a strength of mine.
Joe Alim
[ 00:48:55,910 ] I don't want to be a product designer or product design leader. I don't want to be an engineering leader moving forward. and I find myself kind of doing a lot of that stuff, that's when I'm like, what are my options for doing less of this? Sometimes you're not in the position to hire. You're not in a position to outsource. I completely understand that. But there might be a hard decision to just let the ball drop on some of these areas. Like, you know what? Like, I'm actually, there was a weird, awkward phase where I didn't hire a designer yet, but I didn't want to do design anymore. And I was like, hey, you know what, engineers? Figure it out. Like, here's the requirements. Like, make it look as good as you can. And until we hire a designer, and that was a really tough decision because at first they were like, oh, my God, like you're making us design like we're even worse than you. I'm like, it'll be it'll be good enough. And I think that's like when you're not in a position where you can just hire outsource out. The conscious act of saying, 'I'm going to let this fire burn is like such a hard decision to make. But I think that's like one that you're going to have to repeat over and over again.
Joe Alim
[ 00:49:58,690 ] There's one little thing to add. Someone very early on in my career told me, as a founder, as an executive, think about your time as worth $500 an hour. And think about, is it actually worth it for me to do this, so on and so forth? Is that worth it? And if you act like that, you'll start to filter things out a little bit more appropriately.
Michael Kadish
[ 00:50:18,980 ] I would just also say if you're in the beginning of this it's all about efficiency right and and we live in a world now where so many roles can be filled fractionally or on a contract basis like you could we mean early on in our company realistically we had three people working full time and everything else was contract job this that you know everything obviously you think of you know the bookkeeping our accounting of course or the legal but even like design even these different things like and you can also really get into like, how bad am I? Would a design student do better than me? Would somebody in Romania on Fiverr for $50 do better than me? The answer is probably yes. They're probably going to do a lot better than you if this isn't your
Julie Meyer
[ 00:51:10,970 ]- I'm sure they were great.
Michael Kadish
[ 00:51:13,060 ] And so it really is like probably a better use of your time to manage half a dozen contractors who you find who are efficient, who are just going to do the thing because we all know it's like. Hey, it's going to take me six hours to do that. This is going to take them 25 minutes because this is what they do. They're great at it. I suck at it. Let me pay them. That's how an economy works, and it makes sense, right? And I think even though absolutely, to the gentleman's point there, You never want to be like, oh, I don't want to get my hands dirty with that. I'm too good for that. That's a terrible attitude, but it's. But, and there's plenty of stuff you're going to have to do as a founder that you, that is in that bin. But if you find that like someone is spending, you know, you're spending like days upon days on this thing that you know damn well somebody else could do in a couple hours, that's, you're making a mistake. You are making a mistake there and you don't need to hire someone full time.
Julie Meyer
[ 00:52:07,140 ] And I think when you settle into your role, you're really showing your team that it is important that you stay in your role and that you are leading. And that probably gives them more confidence than seeing you doing everything. We don't have a lot of time left, but we do have time for a few more questions.
Julie Meyer
[ 00:52:24,340 ] Great. Hi.
SPEAKER_5
[ 00:52:26,930 ] So, kind of from a personal experience, so I've got a startup pre-revenue.
SPEAKER_5
[ 00:52:31,430 ] You know, we're making some moves and I'm sort of struggling with bringing either a co-founder or additional talent where I don't have money but can offer.
SPEAKER_5
[ 00:52:40,269 ] Equity and, I guess, the concern is that I see someone I really like, and I like what they bring to the table. How do I value that in terms of equity, and then how do you have that conversation without being, um, you know, without offending the other person about sort of what they want— sort of willing to give up, things like that?
Julie Meyer
[ 00:52:58,600 ] Who wants to answer that?
Joe Alim
[ 00:52:59,580 ] I've had some tough conversations about this in my day. Equity is so much more art than science. You might think it's my idea. I'm the original founder. I'm going to keep 80%, 90% of this company, so on and so forth. But for example, using the technical, non-technical example, if you want a super strong, I don't know if you're a technical product or a software, but in this hypothetical, if you want to hire a top talent engineer, who's going to build the thing for you and you do all the like the go-to-market side of things or vice versa. I view that almost as a 50-50 split, like almost right off the bat, like maybe 60-40, depending on how much responsibility you're retaining. But, like, I would be super generous with that. Think about your future employee stock option pool. Put 20% or 30% aside for that. You're going to get diluted, you know, so on and so forth. But, like, at least originally, I would be a lot more generous than you think. My first split, when it was just me and the first co-founder at the first startup, he took 51%, I took 49%, because he had the original idea.
Joe Alim
[ 00:54:06,490 ] Then we added the technical co-founder. We were about a third, a third, a third. The CEO had to have a little bit more for future board control kinds of ratios and things like that. But my general sentiment is if you're greedy and someone feels like they're not matched or not enough, that resentment is going to kill your business straight away, or at least eventually.
Joe Alim
[ 00:54:28,740 ] You need to make sure that it feels like you are almost equal partners if it's a co-founder. I've never seen a co-founder situation work where it's like, 'CEO, I have 80, 90%, but you're a co-founder, you get three, four, five.' It doesn't feel right if you're calling yourselves co-founders. it's founding team very different than co
Theresa Tribble
[ 00:54:49,860 ]-founders so also distinguishing one minute okay reading founders dilemma by noam wasserman and my co-founders big hat which is an a which is an ai guided antibody discovery platform we built a little spreadsheet and it was basically like each of us. And then we had four phases of the business, the idea, the founding process, post funding, and sort of like terminal. And we taught, we allocated like what were each of us bringing to the table in each of those phases. Like, I got a zero for idea. It wasn't my idea. But I did a bunch of this other stuff. And then we used that as a jumping off point to have the hard conversations about who's going to bring value where. And then we, so we allocated like what percent of value we thought would be created by each of those four buckets. And then we said, which of, in each of those phases, how are we going to do that? It has been used by lots of other people. I give it to people all the time. But it comes from that book. I don't think that they made that, but I think this is what my co-founder abstracted from it.
Theresa Tribble
[ 00:55:53,410 ] So you can have kind of a rational conversation, because this conversation you should also not have in one day. It's going to go like.
SPEAKER_8
[ 00:56:01,590 ] Day one and then you're like, 'Let's break and come back and think about it because it gets very emotional because it's about, what am I worth to you? And do you value me? And so it's a really tough one, but when you get through it right, it can lead to really beautiful, long-lasting partnerships.
Julie Meyer
[ 00:56:16,710 ] They have some of the tools on their website too. Do they? OK, yeah.
SPEAKER_8
[ 00:56:19,780 ] I would hand it out to people.
Julie Meyer
[ 00:56:22,000 ] That's great.
Michael Kadish
[ 00:56:22,700 ] That makes a lot of sense. I'd just say it's very typical to fall in love with the idea that you have. And I think being honest, if you actually map out how far you have to go, it's like, 'Lots of people have good ideas. And it's worth, unfortunately, it's probably worth less on its own than you think.' And I just say a good deal is one where both people think it's a good deal. And to the point, it'll bite you in the ass later if it's too good a deal for you and not a good enough deal for them. Everybody's got to walk away being like. especially your core founding team, like, okay, I'm good. Like, this makes sense to me. You have to feel it too, obviously.
Julie Meyer
[ 00:57:04,130 ] Well, honestly, I feel like we could chat all day. So please get to know the folks around you. Come up for questions afterwards. Thank you so much for having us. Thank you, the panelists. And thank you so much for having us here at Startup Austin.
Jeremy Brown
[ 00:57:22,870 ] Huge thank you to the panel. That was great.
Jeremy Brown
[ 00:57:26,650 ] Let's see, a couple things. For those of you who haven't already heard me say this four times now, there is an ecosystem fair tonight at 6:30. Where you have the chance to check out organizations that are government accelerators, networking groups. So that's just here in the building. The next session that we have here is inventing the future for those that want to stay in this area. If you don't want to use that one, the app will have the the rest of the sessions. And where you can find them.
Jeremy Brown
[ 00:57:59,670 ] And if you're online, just pick your next event. And then lastly, I'll just say for Friday, for those that are in the room that are founders, since I heard a couple of those already. uh at the closing party there is a chance to share your venture and your startup at the showcase uh so you know step by the the desk downstairs and they can give you some information on that so really appreciate everybody's time and the engagement and the panel that was great thank you That was really fun.