In this insightful episode of The Breakout CEO, Jeff Holman sits down with Cydni Tetro to explore what motivates great leaders and how they navigate the complex challenges of business growth and innovation. Cydni is a seasoned technology leader, entrepreneur, and advocate for women in tech, and she shares how her belief in making a difference fuels her work and highlights the power of combining technical and business expertise.
Cydni describes her use of blue sky thinking as a way to surface better options before committing to execution paths. Their discussion also tackles the pressures uniquely faced by CEOs, the necessity of resilience during adversity, and actionable advice for leaders striving to advance their teams, their companies, and their own capabilities.
The Moment: Cydni Tetro found herself leading a company split between two fundamentally different business models. One side generated predictable services revenue, and the other was a growing software platform that required capital, patience, and a different operating mindset. As the gap widened, alignment across executives and investors eroded. What initially looked like a growth opportunity became a strategic fault line.
The Turn: As negotiations progressed to spin out the software platform, the misalignment surfaced clearly in late-stage deal execution. Redlined agreements signaled more than legal tension. They revealed incompatible expectations about risk, control, and long-term strategy. Cydni recognized that no amount of negotiation could reconcile a divide this deep. At that point, the question shifted from closing the deal to acknowledging a level of misalignment that could not be resolved through negotiation.
The Breakout: Rather than forcing an outcome, she stepped away, accepting short-term disruption in order to protect long-term integrity. In later leadership moments, that experience reshaped how she assessed partners, investors, and internal alignment. It sharpened her focus on surfacing assumptions early, testing commitment before capital, and ensuring decision frameworks matched the business being built.
The Lesson for CEOs: Breakouts do not always come from acceleration. Sometimes, they come from restraint. Deals, partnerships, and growth paths only work when underlying expectations are shared. Walking away early can preserve optionality, protect teams, and create space for better opportunities to emerge.
Cydni’s breakout underscores a reality many CEOs learn the hard way: alignment is an operating requirement.
Cydni slowed the process once it became clear that the parties were operating from different assumptions. Continuing would have required overlooking gaps that would resurface later under more pressure, but stepping back allowed her to acknowledge what the process had revealed and avoid carrying unresolved alignment issues into the future. Listen to the full episode to hear how she applies this discipline across leadership, innovation, and high-stakes decision-making.
Cydni Tetro is a technology executive, entrepreneur, and board-level leader with experience building and scaling companies at the intersection of technology and business. Her career spans product development, go-to-market strategy, digital transformation, and executive leadership across both enterprise and growth-stage organizations. She's known for her people-centered leadership style and her ability to navigate complex strategic decisions under pressure.
LinkedIn: Cydni Tetro
Women Tech Council is a nonprofit organization focused on strengthening the technology talent pipeline by increasing the participation of women in technology careers. Founded by Cydni, the organization works with companies, educators, and community leaders to support long-term workforce development through programs, events, and industry partnerships.
Website: https://www.womentechcouncil.com/
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Jeff Holman is a CEO advisor, legal strategist, and founder of Intellectual Strategies. With years of experience guiding leaders through complex business and legal challenges, Jeff equips CEOs to scale with confidence by blending legal expertise with strategic foresight. Connect with him on LinkedIn.
Intellectual Strategies provides innovative legal solutions for CEOs and founders through its fractional legal team model. By offering proactive, integrated legal support at predictable costs, the firm helps leaders protect their businesses, manage risk, and focus on growth with confidence.
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The Breakout CEO podcast brings you inside the pivotal moments of scaling leaders. Each week, host Jeff Holman spotlights breakout stories of scaling CEOs—showing how resilience, insight, and strategy create pivotal inflection points and lasting growth.
Listen and subscribe on your favorite podcast platform:
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Want to be a guest—or know a scaling CEO with a breakout story to share? Apply directly at go.intellectualstrategies.com.
Summary:
00:00 – Introduction and leadership motivation
01:15 – Making a difference through business and community
05:20 – Technical and business foundations
08:45 – Operating across product, market, and execution
12:20 – People-centered leadership at scale
17:40 – Problem solving and reframing constraints
20:05 – Blue sky thinking and strategic clarity
28:25 – The pressure and isolation of the CEO role
34:15 – Breakout moments and misalignment in high-stakes decisions
46:20 – Resilience, action, and lessons for scaling CEOs
Full Transcript:
Jeff Holman (00:01.132)
Welcome back to the breakout CEO. I'm your host, Jeff Holman with intellectual strategies and glad to be back with you guys again today. I've got a fantastic guest. I think I may have undersold this a little bit because I was saying, Hey, I think you're a local legend. And I think in fact, she's much more than a local legend, definitely legendary and probably much more than local. So really glad to have Sid Tetro here with us today. Sid, welcome to the show.
Cydni Tetro (00:28.051)
Hey, thank you. I'm so excited to be here.
Jeff Holman (00:30.274)
Yeah, it's fun having you. I've followed along your career from a little bit of a distance because I'm usually in the audience when you're speaking or getting an award or whatever it's been throughout the years. So I know you've done a lot of things and we'll get into some of those and dive into one or two breakout moments along the way. But give the audience a flavor. Well, wait, I missed my question. So let me step back from it.
Before you give us a flavor about some of the things you've done, I know CEOs are super busy. I know there are a lot of demands both in business and outside of business, family, whatever it might be. And I love to ask guests when I can, what is it that keeps you motivated through all of this? There's a lot of stuff going on, I'm sure. How do you stay motivated day to day?
Cydni Tetro (01:23.147)
That's a great question because some days you ask yourself that question like what's driving me today to do this I You know so firmly built into my DNA is this belief that I can make a difference in like a company that I'm building in the people around me that I can spend my time making people companies individuals the community better
if I show up and do things that help other people. mean, the reason, know, not only do you build companies because you have like great vision and big ideas, but they create economic opportunity for lots of people. They change the lives and ecosystems around you. And because that drives me, sometimes I also make decisions because I like to make a difference. And so for me, that's really what motivates me is like, I really do believe I can make a difference by showing up.
Jeff Holman (02:13.206)
Is there a time when you think back on your career when you said, you know what, that worked out well? Like that person or that organization where it just, you felt like you walked away and said, you know what, whatever else happened today, that happened and I made a difference.
Cydni Tetro (02:19.776)
Hahaha
Cydni Tetro (02:33.097)
You know, I've run companies and I've run a nonprofit. And obviously in the nonprofit world, those stories actually happen quite often. you know, got a couple of years ago, was, the Women Tech Council is a nonprofit. I started more than 15 years ago. And it's just been my kind of constant side thing I've done through my whole career.
Jeff Holman (02:47.864)
Mm-hmm.
Cydni Tetro (02:55.115)
And it's done amazing things in ways I never imagined. But I remember we have a SheTech program where about 40,000 high school girls have come through and about 3,500 of them come together on one of the days in a year. And I was walking down the hall in our tech challenge and there's like thousands of girls and a thousand industry mentors and this girl stops me.
Jeff Holman (02:55.17)
Yeah.
Cydni Tetro (03:14.227)
And she said, hey, I just want you to know that when I was in high school, I came through this program and I heard someone on stage and it changed my life. And then I went to college and I studied civil engineering and I graduated and then I came back and then I entered the job force there. And then I came back today to mentor girls who are in my exact place. And I'm like, yeah, like, you know what? That took eight years, right? As she goes through all of those journeys.
But when you change a life of one individual person in any way, it amplifies their impact in their own communities and families forever. And that's what you're hoping when you dedicate your life to building things, is that the stories you don't hear unfold, and every so often you're blessed to hear some of those stories, and it's really meaningful to those individuals. And you're like, wow, I'm really glad that I'm an instrument in the ability to do that for people along the way.
Jeff Holman (03:57.379)
Yeah.
Jeff Holman (04:05.742)
That's amazing. it's so great when somebody does take a moment and they have the opportunity, they like coincidentally or intentionally they reconnect and they say, hey, by the way, you made a difference in my life. Like you impacted my career. That's fantastic that she shared that with you and that you've been able to do that. I've seen the, I have not, I haven't got three daughters and I have, I think my wife and I have done a good job pushing them into exploring things. I've never been able to get them to the She Tech events.
for whatever reason. So we've missed out on that.
Cydni Tetro (04:36.361)
Wait, are they still in that age demographic?
Jeff Holman (04:39.814)
all three are in college. No, well, they're college age. so I've got one doing a PhD program and anyway, they're college age. Yeah. So, I've seen it. I have an engineering background. I was like, Hey, engineering, engineering, you should look in engineering. And, I haven't been able to get anybody into engineering yet. Although my daughter, my oldest was doing a, PhD in finance and you know, she looked at engineering shortly, but.
Cydni Tetro (04:44.639)
Gotcha. Awesome.
Cydni Tetro (05:05.671)
Awesome.
Cydni Tetro (05:09.424)
So good.
Jeff Holman (05:09.546)
Anyway, great program. I've seen it and the Women Tech Council, yeah, for sure. That's been very active, very consistently strong in the community. Well, cool. Give us a little bit more flavor for what you've, for some of the other things you've done, because you've done a lot and we want to hear, give us the highlights along the way, the last few years or the companies that you've been at that you feel like you've kind of impacted your career and...
led you to the to next thing and the next thing.
Cydni Tetro (05:42.463)
Yeah, you know, there's, probably two things that I think often about one is, you know, I started, I did my undergrad in computer science and, so technology is what did you say? So I did my undergrad at BYU in computer science, and then I did my MBA after that also at BYU. So I really decided early on, I loved this intersection of technology and business. Like the, which is really like the business of innovation in inside of building that. And.
Jeff Holman (05:49.454)
Where did you do that by the way? Where did you do that?
Jeff Holman (05:57.87)
Cool. cool. Very cool.
Jeff Holman (06:09.069)
Yeah.
Cydni Tetro (06:12.199)
So for me, this, the skillset that I've tried to really hone is how do you become someone who has vision to build and then the ability to get people to use it? Which in, you know, the crux of it is customer acquisition and marketing, but.
You know, for me, like the reason you build innovation is because when people use it, it changes their lives and whatever domain that is in. And so my entire career has been anchored in go build cool stuff, build businesses around it, get people to use it, scale that and drive success. And I've had a unique opportunity to do it on a really big continuum. I started my career.
really on the enterprise side and B2B. I came by very well, I started as a software tester in high school, which kind of accelerated my like vision, my identity and visualization into technology.
Jeff Holman (06:53.006)
Mm.
Jeff Holman (06:58.68)
Okay.
Cydni Tetro (07:03.935)
But I really started when I jumped into full workforce after graduation on the product management side. I learned really rapidly these skill sets around how do you go build stuff? How do you product validate? How do you figure out that someone's going to buy the thing that you are actually making and do something interesting with it? And so I started in networking and did document management. And then I gained all of this experience in literally building companies and products and figuring out which ones were not going to make it and which ones were.
which led to an opportunity that I took at Disney to go work in imaginary and basically helping build technology companies internal into the Disney organization. And so anchored in like everything I've ever done has been, you know.
Jeff Holman (07:41.71)
That's awesome.
Cydni Tetro (07:47.392)
Take an idea and whether it's in a large enterprise that you're building a new project or a brand new thing and being like, okay, why are people gonna buy it? What are the limitations of it? Who's gonna end up using it? How are we gonna price that? What's the feature set? How do you build minimum viable product? What's that user experience? And then what channels will someone even find this in and can we scale it significantly enough?
And the answers to those questions have led me to build businesses, kill projects, start new projects, or pivot them in order to drive that. And that thread took me through my work at Disney, through then starting my own companies in the 3D printing space and in digital transformation, building some really big CPG brands, all the way basically through anything I've done. That skill set anchors me every time.
Jeff Holman (08:20.578)
Mm-hmm.
Jeff Holman (08:30.584)
Well, so you've got the, you've got the duality like, I, I wonder if you struggle with the same thing and struggle, maybe the wrong word. I wonder if you struggle or benefit or, have the same thing I do. Cause I've got my engineering degree and then the law. then I, I always wanted to get a business degree and be more business than anything. So, but I feel like these things, they're very complimentary sometimes, but they're also very orthogonal. They don't necessarily go together all the time. And so I'm like, am I
Cydni Tetro (08:56.896)
Ready.
Jeff Holman (08:57.582)
Am I having an engineering conversation right now or a law conversation or are we talking about business? Do you see those as parallels or are they one unified personality for you or what do you do with that?
Cydni Tetro (09:12.779)
Yeah, that's a great question because you're right. Sometimes they have like this own internal battle in your mind where, you you throw me in a technical room where we're developing product and like, love the building of innovation. I love like thinking about, I'm sorry, that user experience is actually not going to work. Right. I'm sorry. You created too much friction. You're going to never get someone down that path of usage. You don't have a million users today. You have zero. How are you going actually get someone to build that?
and then that business side of you. The thing I find most interesting when you have both of those skill sets is people don't know how to handle you because people don't know if when you show up in a room, you're going to, they don't expect people to be able to wear both hats. And so the crossing the chasm between those two worlds, people are either surprised or it's unexpected or they don't believe it can be true.
Jeff Holman (09:55.075)
Yeah, yeah.
Cydni Tetro (10:04.905)
which I think is really the interesting side. For me personally, you do sometimes have to wear those hats. I loved the blending. I remember being in college and saying, I firmly believe that having an understanding of how stuff is built and being able to build it and go really deep in technical and architecture and adding business to that is gonna take me places I can't imagine today, but the combination of those two will be powerful and I'm gonna do it.
And so even back when I applied to grad school, like that was my thought. didn't know where it would take me in my career. I just knew that it would be really interesting.
Jeff Holman (10:30.155)
Yeah.
Jeff Holman (10:38.808)
No, that's, I totally understand that because I went into engineering and people are like, you want to be an engineer? I'm like, no, I don't think so. But I really want to be, I want to do engineering cause I think it's going to be a great foundation for business. I don't know what I want to do. If you asked me when I was 16, what do you want to do when you grow up? I'd be like, be rich. Like that was my only answer. had no, but I loved, you know, the engineering side and I'm like, well, that sounds like it'd be a good foundation for getting into business. What am I going to do with business? I don't know, but I'll figure it out.
I think it's a great combination. I love how you said people don't know how to handle you. It reminds me of one time I had a friend, know, I have a small law practice at one point, I don't know, 10 or 15 years ago, a friend's larger law firm was talking with me about maybe merging our practice or buying or whatever. And they said, they looked at all my stuff and they're like, we really like your practice. We really like what you're doing. We'd like to figure out a way to make this work.
We just have one thing and Jeff, we're not sure what to do with you. It's almost like you kind of fit in everywhere so you don't fit in anywhere sometimes it feels like. I don't know if you get that same feeling.
Cydni Tetro (11:54.268)
Yeah. Yeah, sometimes you do. I think that people, because we like to put people in a box. Like you're a technologist, you're a finance person, you're really good at marketing. And when you're multifaceted, people end up putting you like in this general category of operations, which sometimes you feel offended by. Cause I'm like, oh yeah, I'm like a hell of a good operator, but that's not like who I am. Right? Like the magic that I think I bring to a team or an organization.
Jeff Holman (12:18.615)
Right.
Cydni Tetro (12:23.243)
is the ability to go deep in really many disciplines and then abstract those in order to say, hey, like we're going to take a path to get here. Like throw me in your technical conversation. I'm to go super deep and we're going to end up with a better product because we're collectively working on that.
And I'm going to go figure out how to do large strategic deals and go to market strategies with those teams and take those to market. And it's unexpected. And so I think it's just an interesting reflection because I do think when you talk a lot about breakout kind of moments.
People who are great at breakout are multifaceted, which I think makes them hard to identify and understand and become because it's not just one facet of them. They're multifaceted and it's kind cool that those surprises and who you can become lead to cool new things.
Jeff Holman (13:14.754)
Yeah, so, and you started this early on. I imagine you weren't necessarily surrounded by all of your girlfriends in high school who came on board with you to do software QA as an after school job, right? So you've been kind of standing out. I'm curious, do you have a way or a word that you use to describe your leadership style? Because I think a lot of leaders, they think, okay, I'm...
Cydni Tetro (13:27.179)
Right.
Jeff Holman (13:44.268)
I don't know, I'm really good at culture or I'm really good at vision or I'm good at innovation. I have a lot of ways that I describe different leadership styles, but I'm really curious without putting my terminology onto you, do you have a way that you would describe it?
Cydni Tetro (14:02.811)
That's a great question. I think I would describe myself as a Like I'm a very people centered leader Who like I want big bold fast execution
Jeff Holman (14:11.779)
Mm-hmm.
Cydni Tetro (14:20.309)
but that doesn't leave people in the wake. And I...
Jeff Holman (14:23.98)
Yeah, well, because if you did, if you were leaving people behind, wouldn't, you wouldn't be having the type of impact that you already talked about wanting to make. Right. So.
Cydni Tetro (14:30.547)
That's right. Yeah, like I, so for me, it's like the mix of those things. Like I anchor myself oftentimes in creative problem solving, but I'm not sure that's how I corely describe like the leadership style, but.
like building big impactful, powerful things with people. Like I don't believe that I'm ever going to build it alone. I don't have all of the best ideas, but I'm going to galvanize teams of people. And I also want people to come and like be part of that team and see the vision and jump on board and just help move forward and take care of the people along the way. And to be fair, it's an imperfect world. Like I wouldn't say that, you know, like every person does when you're a leader, not every person ends up loving you. So even though you want to be people first, um, I subscribe to
Jeff Holman (15:04.749)
Yeah.
Cydni Tetro (15:13.197)
the statement that often gets said like 30 % of people are gonna hate you 40 % of people never care about you and 30 % of people are gonna love you and somehow you have to become good with that even knowing that your style is driven by the people that you care most about
Jeff Holman (15:27.298)
Yeah, I imagine that that gives you an opportunity actually because of your multifaceted nature and skill set and you're seeing the business objectives but you still are focusing on the people and yet you're an innovator and so if I had to guess, bet you actually thrive finding solutions that maybe combine those things where other people wouldn't expect it. It'd just be like, no, it's the numbers, get the numbers, hit the numbers.
and everybody would be happy. Or no, no, no, you gotta have culture and you know, maybe the numbers have to give, and you're like, wait, maybe this is a puzzle I can solve better together than if I did one or the other. Is that ever, is that?
Cydni Tetro (16:08.491)
Yep. so interesting you say that. was in a meeting last week with, as I've been like helping kind of
do some restructuring on a company and helping them fix their economics and some of their business operations. And we were sitting in this room and there was one specific area that the week prior, over the last couple of weeks, I put one of the team members, I'm like, come back with the proposal, go figure out this and come back. And he walked into the room last week and he laid out this proposal and...
the way that it all happened, he started asking a whole series of questions. So the thing that he was going to solve had been in operation for years. And he came to the table and he said, okay, well, the thing that you asked me to solve and how we were gonna measure success, I went and met with the team. I asked all these questions. And did you know that these 10 things have been true that were never supposed to have been true that could have unlocked all of our opportunity in that space had we asked the questions. And for years, no one had asked them.
Jeff Holman (16:45.251)
Mm-hmm.
Cydni Tetro (17:07.787)
I'm like, isn't that fascinating that we end up in these lanes where we think the constraints of the world are as we're executing today because someone set them up and there's no way around them. And we forget that a lot of times you have to be able to think about the blue sky, think about the art of the possible and say, but wait, if those things weren't true, what happens? And
Jeff Holman (17:07.982)
They just.
Jeff Holman (17:23.16)
Mm-hmm.
Jeff Holman (17:26.638)
Yeah.
Cydni Tetro (17:27.709)
And that's hard for a lot of people because they're like, well, someone said you should drive this way every time, or you should follow this process every time you step into this. You're like, but wait, the problems that have gotten created, you can't solve them in the same way you created the problems. So if you're going to break through problems, if you're going to solve solutions, find solutions, you have to come up with new ideas you didn't imagine before because your old way leads to the same outcomes that you have right now. And if you keep doing the same thing, it will never change.
Jeff Holman (17:42.872)
Mm-hmm.
Jeff Holman (17:56.11)
I think my, I can totally relate to what you're saying and I think my team gets sick of me because I go to them, I'm like, there's gotta be a better way, right? We've got this, we're trying this, but isn't there a better way to do this? Like what's, and I think it's a double edged sword sometimes, because maybe you find this, you're like, hey, I see multiple perspectives here and I think I can find a better way. That puts a lot of pressure on yourself to be.
Cydni Tetro (18:14.027)
official.
Jeff Holman (18:24.428)
you know, maybe the one leading the charge to do something nobody's done before, because it seems like you should be able to kind of mesh these two worlds together or plug these two, you know, courts together and make it work. Do you find that there's a different type of stress sometimes in those situations?
Cydni Tetro (18:36.074)
Yeah.
Cydni Tetro (18:44.307)
For sure. I've because of that skillset you're talking about. find myself naturally wanting to be the problem solver always, right? Like you come and you're like, you know, someone will come in the room and they'll say something like, but don't you think other people build successful businesses like that? There has to be some way someone figured this problem out because other people are doing that. But your teams don't know how to adapt to that. In some cases, I also think another interesting, just making me think of kind of a different side of that.
Jeff Holman (18:52.216)
Mm-hmm.
Jeff Holman (19:01.356)
Yeah.
Cydni Tetro (19:12.745)
know, there's been some times when I've stepped in and I've run companies for board members. And my natural, for a board and for investors, and my natural tendency is to be that problem solver all the time.
And to like try to take the inputs and the outputs, the outcomes of how people are measuring success and build something that achieves those. And the thing that I've had to figure out how to do is how to step back sometimes and say, do you know what? Well, I think that might be the outcome they want. It might not be. And actually turn over that creative problem solving to someone else. Because sometimes I've been in situations where I helped people solve problems in ways they were never going to imagine that were really brilliant at the time, but were probably
not the right thing that I should have done because I solved it for them. The responsibility also comes to you. sometimes you have to... That's right. In other words, maybe the solution isn't wrong. It's that their decision-making framework's different. And so you came up with a solution that was totally going to work, but misaligned with other people on the team. So I think when it's in your DNA to be that person, you also have to find places where you're willing to step back and be like, yeah, I might not get solved the way I can imagine. It doesn't matter.
Jeff Holman (19:58.958)
Not that the solution's wrong.
Jeff Holman (20:08.301)
Yeah.
Cydni Tetro (20:21.706)
because the accountability of the end decision isn't going to fall on my shoulders.
Jeff Holman (20:25.516)
Yeah, and scaling too, right? You just can't scale if you're always the problem solver. so, yeah, it really does seem like a double-edged sword. And I love that you're explaining this in a way that I think I can relate to, and I'm sure many of our audience can relate to. Is this a central theme to some of the things that you've been able to do in companies over the years when you've, you know,
Cydni Tetro (20:28.228)
yeah, you can't stop.
Jeff Holman (20:53.526)
either started your own company or maybe stepped into a company or you're running the team and you kind of hit these walls, you find yourself on a plateau and you're like, do we get to the next level? Like is this, how do you draw on these skill sets or other skill sets to address those issues?
Cydni Tetro (21:13.684)
Yeah, that's a great question. So in my mind, I call it, I kind of call it blue sky thinking. So when I was at Disney, there was a dedicated group in imaginary and called the blue sky group and their number one job.
Jeff Holman (21:19.406)
Uh-huh.
Jeff Holman (21:25.326)
Not blue ocean. is so this I think a lot of people are familiar with blue ocean stuff, right? Blue sky is different, right? Okay.
Cydni Tetro (21:29.97)
slightly, but at Disney it's called the Blue Sky. And the Blue Sky's team, like their specific job was to like think about any idea without constraints. like, what could be possible if is the question that I generally ask.
So if we didn't have the financial constraints or the resources constraint or the time constraint, what would be the thing in this space that would change the world? And I love the blue sky mentality. So when I think about blue sky, actually, it's really nice blue sky today. If you look outside the, the power.
Jeff Holman (22:04.32)
It is fantastic. We need some snow, but it's fantastic.
Cydni Tetro (22:08.032)
Yeah, it's 60 degrees, but it's fine. The blue sky, when you look at it, there's no limitations, right? And similar to the idea of the blue ocean. But what I love about the sky is it's infinitely massive. There's no obstructions. If there's no clouds in the sky, there's nothing that impedes your view or your vision. And you can go clear into space forever. you could just imagine infinite possibilities.
That mindset is very, very challenging for people to think about the blue sky mindset. And what I find in teams is the thing that I'm always trying to unlock for them is don't live in the constraints of today. We will get to constraints. To drive execution, we're going to make trade-offs. To drive execution, we're going to get to a path that says we can do one thing and we'll get to this outcome. But before you get there,
think of the world that has no constraints because that becomes the goal of which you can obtain and if you can reach that goal then we can if we can if we can see that goal if we can see what can be possible we'll come back to a plan that ultimately executes that.
That mindset is really hard. And I even remember the first time I did this exercise, I did this brainstorming exercise and I often do it with teams, pull them into a room and like, okay, we have a set of problems we have to solve. And all of you are coming together with preconceived expectations about how this could be true and what you're responsible for in your domain or the pressure that you're feeling. And I need you out of that space so that you think differently, but different teams react differently. did this exercise only about a month ago with the team where, you know, I start with like a word association and how
them brainstorm off of words. And this entire team, it doesn't usually happen this way, every word that someone wrote down, because I'm always like no constraints, any word that comes to mind, there are no bad words you could say, like just let your mind go to wherever the connections make and I take them through this whole exercise, every person in that room kept going back to the original idea that I had them start with, which was grounded in some business problem. And they had such a challenge breaking out into other thinking. And as we got through the end of the exercise, I pulled back and I said, did you see how
Jeff Holman (24:05.719)
Yeah.
Cydni Tetro (24:10.015)
Every decision you made was constrained by you wanting to be right with your problems, so much so that you didn't let the solutions come. And when you don't let the solutions come, you don't find out that no one ever asked a question to completely change a business. And now that we know we're going to change everything. And so I work really hard to empower my team members to say,
Jeff Holman (24:14.414)
You
Jeff Holman (24:25.955)
Yeah.
Cydni Tetro (24:30.657)
What, cause I feel like leadership teams, your job set strategy and solve problems. and how do you, about like all the things that are going well, we're like, awesome, please keep doing those well. But the problems are always the thing that you're unlocking in a business. as a CEO, you spend all your time on people and the strategic challenges that the business have that if stayed true require massive change. And so you're trying to mitigate risk every day. And in the mitigation of risk, you have to wear a different hat. If you are a hat that says,
We'll solve it the same way. You never break through it. You have to be able to come in a room and say, I know all the constraints. I get the financials. I get the people. But if we don't solve this, what happens to business? And then what are our options? Where do we go? And then how do you empower team members to walk out of that room and say, yeah, you go take this on. You go do it. You come back to us. It's in your accountability. You own it. And when you come back, we're still going to ask you all these questions about what could be true. But we're hoping you're now oriented in a way where
there aren't bad ideas, think through those possibilities and come back and we'll then use the collective group to help continue to mold that. Every time I've done that, the teams are better formed and they're better built.
Jeff Holman (25:38.52)
Yeah.
Have you ever used the six hats approach where you assign every, I think there are colors, I don't remember what the colors correspond to, you know, one of them, it sounds like you're taking everybody and you're saying everybody wear the white hat or whatever color it is where you're just unconstrained. Have you used the six hats approach too where you're like.
Cydni Tetro (25:59.564)
I've never used to the six hats. That's an interesting question. haven't, I've kind of anchored myself in this blue sky methodology and kind of the design thinking stuff around it and used that as my.
As my tool set, I would also say my, yeah, so I haven't ever given people roles because, maybe my tendency for not doing that is that not everyone has equal skillset. And so you're trying to help them unlock new skillsets, but I tend to find that if I try to place someone so uniquely in a different bucket, while the intent is really helpful, it's more challenging for them than if I can give them tools that like help them guide people forward. And even in the last couple.
of like months or so as I've been restructuring a little bit of a team, I gave an assignment to someone and then the next and I'm like, come back. And so he comes back the next week and he's like, okay, all the things that we talked about, I don't think that's the path we're doing. Here's my recommendation. We did the analysis, right? All of this thinking. It was completely 180 from where we thought we were gonna land.
Jeff Holman (26:59.896)
Dora.
Cydni Tetro (27:01.525)
comes back the next week and he's back to the other position because of all the additional conversations. And it was a really fascinating process to watch, but he did it. He did it rapidly, but with all the series of questions and a whole new framing for how to analyze it, he needed to take that pivot and come back. Now he's a hundred percent bought it. And then he's going to go execute that plan.
Jeff Holman (27:20.887)
Okay.
Cydni Tetro (27:22.495)
And so I like accountability and people moving quickly, giving them timelines, giving them frameworks, because if they'll come back, and it doesn't matter if it ends up being my plan, it just has to be the one that gets our measures of success, they'll actually execute the work to make it happen. And that's what you team members to do. You can't possibly do all the work. You've just got to be really fantastic in leading people to get to the same objective that makes your business successful.
Jeff Holman (27:47.586)
Yeah. No, I've, I've, I've loved as I've talked to more and more CEOs on the podcast, I've loved the theme of people. mean, it's just, it's the most central theme that we've had across every episode. So, it's, don't know if it's surprising to me, but it's, it's definitely apparent that people are the central point of what we're doing now. Money's important business model strategy, but, you can't doing it without, without leading it, having the right people and, leading the
leading people in the right way. how is how is this
Cydni Tetro (28:18.315)
I think so. I think the reason it's surprising is because there's also lots of bad leaders. Right? And the stories that we hear are, what do mean by that? Like there are rooms that people walk into where it is command and control. No one else's ideas matter. No one feels empowered to show up in their conversation. They're like, I'm here to take notes and whatever you say I better do because otherwise I'm getting in trouble. There are lots of those rooms.
Jeff Holman (28:24.494)
What do mean by that?
Cydni Tetro (28:45.843)
And actually, I think they're the majority of rooms that people work in, which is why I think people say it's surprising when, because people talk about people all the time, but they don't show up like that in work environments all the time. So it's different to talk about.
Jeff Holman (28:54.307)
Hehe.
Why do you think that is? mean, because it's like a fundamental, right? Why do people show up differently than what maybe they know is needed? Is it just innate in somebody? They just can't help themselves? Or is it the pressure? Because I think of some people I've worked with and I've worked with good leaders and I've worked with people who might be called bad leaders for various reasons.
Cydni Tetro (29:10.671)
And the.
Jeff Holman (29:27.31)
What are the struggles? Sometimes I wonder to myself, as an attorney, I've actually walked into people's offices, the CEOs, and I say some things sometimes that maybe nobody else in the company would say. I'd be like, hey, you can't say that. Maybe for legal reasons, maybe just as a friend, let me tell you that that isn't gonna work in this culture or this setting or whatever. And I don't know that I feel empowered to do it. I feel responsible to do it a lot of times.
Cydni Tetro (29:43.137)
Sure.
Cydni Tetro (29:55.789)
Thank you.
Jeff Holman (29:57.262)
And I've come to the conclusion that a lot of CEOs, there's a lot of stress on CEOs. I think some CEOs, their personalities hinder them from being good leaders. But I've wondered if a lot of times CEOs maybe fold to the pressures and they're not bad people per se, you know, but they adopt or try out some of these maybe tactics.
that come across as if they're bad people. Do you know what I mean?
Cydni Tetro (30:29.452)
Yeah, I mean, I think.
It's so complex, right? When I think about the structure of things that I think make bad leader, I think that is sometimes true. The pressure on a CEO, unless you've sat in those seats, you don't fully appreciate because you really do feel the weight of investors' money you've taken, the employees who work for you, building the success of the company, reputation, all of those things. You live and breathe them every day and no one else feels mostly isolated.
Jeff Holman (30:57.728)
And you're isolated sometimes, right? Like you, I've talked to a lot of CEOs and they just don't feel like they can turn to their team because you can't tell your team all the problems always. And you can't necessarily take all the problems straight to the investors or the board members because you know, you're trying to be competent here too. And you don't always have peers. Like it's a tough role to fill. It really is, I think.
Cydni Tetro (31:19.98)
It's a really tough role to fill. And so that pressure I do think changes the way people show up and behave for sure, depending on the stress sitting in a business and the decisions that you're trying to make. But I think even through those most stressful times, there are skills that you can show up with. But I think a lot of times in those bad leaders, you end up with people believing that they have to visibly always be right. Like they insecurities about
Jeff Holman (31:27.086)
Mm-hmm.
Jeff Holman (31:48.492)
Yeah.
Cydni Tetro (31:48.675)
Deficits that they have as a leader and they compensate for them by You know belittling people or putting them down or not letting them speak A lot of people when you move especially in smaller companies from an individual contributor role to a leader role you Think the way you have done stuff because you were such a high functioning individual contributor is the way you show up as a leader
Jeff Holman (32:09.358)
Mm-hmm.
Cydni Tetro (32:11.502)
And because as an individual contributor, people pat you on the back. They're like, Jeff, you're such a fantastic attorney. Like, come in every one of these rooms, like crush it for every, know, everything we're doing. And then when you go to a leader, no one pats you on the back. No one's like, did you know you're such a fantastic leader? Because now your job is to pat on the back all the people who work for you.
Jeff Holman (32:11.694)
Yeah.
Cydni Tetro (32:28.854)
Now your job is to make all of those people so high performing that your team's successful. That's a different game. That gap is very significant for people. And then when you take that gap even further to the stress of a CEO, if you haven't learned how to be a good leader on the way, it's really big. I will say the first time I became a manager, I was a horrible manager.
Jeff Holman (32:28.856)
Yes.
Jeff Holman (32:49.486)
I think that's, I think that happens to a lot of people though, for the reason you said.
Cydni Tetro (32:52.918)
I was so bad. Yeah, because I'm like, I'm such a great individual contributor. I crush it. I know exactly how this job works. I know exactly how all the people who work for me should be doing this job. And why aren't they doing it exactly like I say? then it tastes great.
Jeff Holman (33:04.321)
Yeah, know what motivated me and I'm a high performer, but of course you were probably the standout performer for a reason, right? So what motivated you might've been different than what motivates the other team members that, yeah.
Cydni Tetro (33:16.238)
Yeah. And so it becomes a journey, you know, of becoming that. so CEOs who either get thrust in that because they start a company and never had the journey. That's one thing. But then I find a lot of leaders, they step into these roles. There was a leader of a very large organization and I was on the executive team and she particularly was very insecure about.
Jeff Holman (33:24.462)
Mm-hmm.
Cydni Tetro (33:39.171)
the skill sets of being that leader. And it showed up in the interactions of the team members. And so we see this in all sorts of places, but I very much believe it comes down to you haven't learned what it means to pull teams along like that. And also it's a choice. Sometimes people who become really seasoned leaders, they're like, this is the style that works for me and I'm just going to be this person and there'll be casualties along the way and who cares?
Jeff Holman (34:01.678)
Yeah
Cydni Tetro (34:05.63)
And so I kind of decided, and I also recognize in my leadership style, that I'm in the minority. I've very much come to realize that my leadership style, the thing that I expect for people, how I expect to show up, isn't the standard. It's not gonna sit in command and control. I'm gonna try to empower people.
And I'm actually okay with that and it's not going to work for everyone and I'd rather be that leader than a different leader. And I'd rather know that the majority of people who end up working with me still want to work with me again in some capacity if that opportunity became true because I figured out how to leverage their talents, put them in interesting roles, expand those and that won't be true for every person that works for me. But I do want to show up as that type of leader and I'm okay with sharing information and being transparent and having people have information so they make better decisions.
because you're not in the room all the time and and the more that you empower those people and you support them the better shot you have of being successful and I'm just not going to walk away from that philosophy even if it doesn't play out correctly every time.
Jeff Holman (35:09.292)
Yeah, no, and the fact that you recognize it and you own it and you know, when somebody comes to you and hey, we've got an opportunity. You can be like, well, here's how I lead. Like you can be upfront and transparent about it. And if that's a good fit, then fantastic. And if it's not a good fit, then you know that upfront and you don't have to struggle through the misalignments and stuff like that. So I am just looking at the time and I appreciate all this conversation. I want to get to a breakout moment and I'm wondering if...
Cydni Tetro (35:34.028)
I know, sorry.
Jeff Holman (35:38.27)
you know, some of these things we've talked about, have they contributed to a moment in one of your companies that you've been leading where, you know, you're up against a wall, you were hitting a plateau and maybe you, you know, stepped outside the box for new perspective or you got some, you know, insight from reading something or hearing something or talking with somebody. And that created a shift for you, for your team that kind of led to the next level.
Have you had a moment like that that you could share?
Cydni Tetro (36:10.831)
Yeah, I feel like I've had so many of those moments in like almost every different facet of my leadership ability in a given skill set. I feel like there's been something that just fundamentally altered my course because of that. know, one, I'll give you one that particularly that came to mind that's kind of different from some of the other ones that we were talking about. So I had...
I was right. had stepped in to run a company and the company was very much around in the digital transformation space. And we had, I built this whole software platform with a team of people, which I really, really loved. But the interesting thing is we had originally started the company from a consulting mindset and
Jeff Holman (36:47.299)
Mm-hmm.
Jeff Holman (36:56.056)
Okay.
Cydni Tetro (36:57.903)
We started the cup, which is an interesting one where you start as services and then you build a platform It's a pretty big journey for certain types of people who come out of services versus platform They're not the same and yeah
Jeff Holman (37:06.786)
And they're not the same at all. Like they're totally different business models. Like you're the same team, but totally different models, mindsets, know, financials. they're two different businesses, even though they happen to be under one roof, right?
Cydni Tetro (37:20.827)
And not everyone appreciates that. And the switch to that is big as you well know, because you're wearing both those hats all the time in your business. And so I had two really interesting breakout moments. So one is, like you just said, these business models are so different. Services is like cash in, cash out. You know exactly what the valuation is. You're to go close kind deals. You're going to bring that in. But in the product model, you're going to go best in building a product.
and it's going to have a little bit, usually a different cycle of payback. And you're going think about AIR and you're to think about valuation. And the two groups of people on the investors and executive team were very split. They didn't align. And,
Jeff Holman (37:50.67)
Mm-hmm.
Jeff Holman (38:04.718)
Oh, okay. They had proponents for each one. They're like, no, I like this better. Let's stick with what we know. No, no, no, let's make an investment. Okay.
Cydni Tetro (38:11.224)
Yep.
Yeah, and it was a interesting battle for months, like seriously months. And so much so that I had gotten to a point where I'm like, think the very best thing is going to be for us to find a partner and an investor who will come in and potentially buy the software side of it because the business was so anchored in services. so I like, and this has happened to me.
Jeff Holman (38:37.646)
How did you come to that conclusion? Was that like picking sides? mean, was there real turmoil between the two sides? Were like really strong advocates or, you know, what was the team like at the time that that was going on?
Cydni Tetro (38:55.967)
very strong advocates. It was becoming more more clear every day because a services side of the business was still operating. And so you have the services side of the business that was still operating, which is obviously making more money than the product business as the product business starts to scale. And that chasm between the two was getting bigger and bigger constantly. Yep, exactly. I mean, overall, the company...
Jeff Holman (39:09.368)
Hmm.
Jeff Holman (39:15.608)
Were people like, we're carrying this and we're having to divert funds and how big was the company more or less? mean, was this a either in revenue or people or.
Cydni Tetro (39:25.485)
You're talking kind of like, you know, upwards of 10 million. You're not talking like a hundred million dollar company. So it's small enough that it matters where dollars are placed, you know.
Jeff Holman (39:34.134)
Yeah, yeah, that's a bit any money coming out of $10 million and service based businesses, you know, I talked to a lot of my law firm friends. I, I try to my business more like a business than a law firm, but a lot of law firms, you're like, Hey, do you have margin? They're like, what do mean? I, I pay myself what I make, right? They're, don't, there's no concept of margin. And when they say, yeah, we have a margin. That margin really is just the end of your income for them personally, not, not really margin in a typical business sense. So there's.
Cydni Tetro (39:50.124)
Right.
Cydni Tetro (39:58.926)
Okay.
Jeff Holman (40:03.534)
$10 million, that matters a lot.
Cydni Tetro (40:04.307)
Exactly. Yeah, it matters a lot. And oftentimes when you place a bet on the software, it's because you see exponential returns eventually, but it's a different path to get there. And we had funded it with some services revenue that had come in originally, which led to this product innovation. But you could see this gap getting wider. It was very visible. And so I was like, what should I do with this? And how do we get all parties satisfied?
Jeff Holman (40:22.904)
Mm-hmm.
Cydni Tetro (40:32.653)
So I ended up finding a partner who's very interested in the company. Actually, we go to term sheet and we're in the path of definitive docs. So we're now into due diligence and we, you know, we structure. You're almost to the finish line and we're send back our definitive docs and my partners on the business said when they reviewed the docs,
Jeff Holman (40:40.75)
Mm-hmm.
Jeff Holman (40:45.304)
Just almost to the finish line.
Cydni Tetro (40:58.383)
I won't blame this on an attorney side, but their mentality, I have a mentality. I'm going to blame you. So what we did, you know, when I do business transactions and I've done a lot of like financing and M &A and raising capital, you know, I'm very like specifically know like be aligned in the outcomes, right? And negotiate the big points that really are going to make an impact. Well, the agreement in the, we're in definitive docs comes back to our partner with six, with almost 70 % red lines.
Jeff Holman (41:01.878)
It's okay. That's our job. Blame us.
Jeff Holman (41:29.379)
Wow.
Cydni Tetro (41:30.383)
And we've gone from term sheets, signed term sheets, to due diligence, to definitive docs that go across with 70 % red lines in them.
Jeff Holman (41:33.25)
Yeah.
Jeff Holman (41:39.214)
Do you know, is this a situation where the business leaders have negotiated the term sheet and the attorneys weren't really involved and then you give the term sheets to the attorneys and they over lawyer it? Was that an issue or was it something else do you think?
Cydni Tetro (41:56.528)
a bit, I think you ended up with two really interesting things. it's for sure over-lawyered, i.e. I wouldn't use this language, so I'm gonna change the language, right? Kind of things, it's not a big deal, it's just mostly red line, blah, blah, blah. But also a different philosophy between the business and the investors in how you approach legal agreements. And fundamentally of like, so some people...
Some people let their lawyers define the edits, other people, the business people define, and your lawyers are your partners. They're two different philosophies. And these guys are like, our attorney said this is what we should do, it's not that big of a deal, and send it over. So they send the stock over. I get the phone call that says, this basically looks like you guys don't want a deal, that's what we're reading from this. And I'm like, yeah, of course it looks like that. So I go back, we have this huge meeting, and...
Jeff Holman (42:31.895)
Yeah.
Jeff Holman (42:43.032)
Mm-hmm. Mm-hmm.
Cydni Tetro (42:51.215)
my guys, the two factions still exist. And they're like, okay, that's fair. We'll go back and we'll make changes, know, blah, blah, blah. But the sophistication on what it took for that type of a business was not deeply appreciated. The chasm was still existing. So the new version comes back 60 % red line. And I get a phone call and the guy says, I'm gonna, hey, can I fly down and meet you tomorrow? And I remember going, the only reason this happens is the deal's completely blowing up. And this is over the course of less than a week.
Jeff Holman (43:18.797)
Yeah.
Cydni Tetro (43:21.283)
And I've had two instances where things like that have happened at the very last moment of an agreement. And I remember saying, knowing that I couldn't save it. Like, I was then in a position where, you know, something was, you know, that I had like helped build and grown.
I was at such a chasm from other stakeholders in the ecosystem and there was no bridging of that, that it fundamentally had to change how we went for it. Ultimately, we ended up separating waste out of that because there was no way.
Jeff Holman (43:43.63)
Yeah.
Jeff Holman (43:55.244)
You mean the services and the services of the product in the business separated? Or the deal parties left? you left, okay. Yeah.
Cydni Tetro (44:00.246)
No, I left. The deal left, the deal disbanded and most of the leadership on the product team exited because there was no way to come back. And I've often thought, and it was this like breakout as relative, but it was this moment where you're like, okay, what are the rules that you now engage in to figure out how you get people better aligned time and time again? Because when someone sends over the 70 % red line, all it does is send a flag. And when no one believes you that it sends a flag,
Jeff Holman (44:11.308)
No path forward.
Cydni Tetro (44:29.411)
then you're forever going to be a chasm so wide you can't cross it with stakeholders.
Jeff Holman (44:34.37)
Yeah. And, and I don't, this isn't a legal podcast by any means, but for the business people out there, like I've, I've seen this happen. And I know, I know people, know attorneys who they do this on purpose, whether their clients ask for it or not. They love to put in little gotchas. They love to make language that should be really clear, ambiguous. And, and, and they do it because they feel like they're
Cydni Tetro (44:38.455)
I'm sorry.
Cydni Tetro (44:49.967)
sure.
Jeff Holman (45:02.69)
doing some contribution to the deal. And this is where I have a real struggle with that approach because, and I've been on the opposite side of that and I'm like, why would you do this? Like, does your business, your client really want to deal? Because if they do, why don't we just do the deal that's been, that the business people have already agreed to instead of trying to be creative or thinking that you're protecting them.
Cydni Tetro (45:23.139)
That's right.
Jeff Holman (45:31.852)
when what you're really doing is introducing a ton of risk into the deal. it's, I don't know, I think business leaders should not only make sure that their team is aligned, but a lot of times we just hand this stuff off, because I've been in house counsel and you're like, hey, we need this done. And you hand it off the outside counsel without a lot of instruction and not even like instruction like, hey, type this or that. It's more like, hey, here are our objectives.
Cydni Tetro (45:35.791)
That's right.
Jeff Holman (45:59.394)
we, you know, this is a deal we wanna get done. Here are the major risk points that we think we've already addressed. Like being aligned with your legal team is so important and it's frustrating because those deals, if they do get signed, they'll often fall apart anyways. And when they fall apart after signing, you know, it's just as big of a problem if not bigger. So anyway.
Cydni Tetro (46:16.794)
That's right.
Cydni Tetro (46:22.02)
Well, I actually just like the thing I've come to believe is what you just said, which is it's not about the attorney or the legal. It's about a fundamental disconnect on business strategy. And it's about a fundamental disconnect on what it takes to make something successful in the deals that I've had blow up on really large deals, know, fundraising, like tens of millions of dollars and not, and, then those moments becoming the moments where I appreciate that my other investors and I are not aligned on the reason we take this deal, even though we're all the
Jeff Holman (46:31.106)
Mm-hmm.
Cydni Tetro (46:52.024)
that far down. And so for me, when I think about like breakout moments, anything, every conversation that you have to have to de-risk and understand the reasons that you have gaps, what you can overcome and how you have to show up in that space and the decisions you personally have to make for how you engage with that team and those are yours to own. Because you do have many people around the table and you don't get to control them all.
Jeff Holman (47:12.942)
the
Cydni Tetro (47:15.92)
Right. And the moment that you have other people in the mix, they're going to create other variables. They're not going to look the same as you. And so the better that you are as a leader in those spaces of being able to identify them, have the conversations and make a personal assessment, the more rapidly you'll be able to figure out if you can take the company where you want to, if you need to go engage in other partners or what your next step is going to be. And that's a really, really hard thing to learn, especially when you are an inventor and make and make stuff like when you want to be the creator of things.
Jeff Holman (47:16.227)
Yeah.
Cydni Tetro (47:45.874)
and it means that you potentially put at risk things you create or people that you hired because of dynamics that they are unaware of.
Jeff Holman (47:53.676)
Yeah. Well, and sometimes we let the idea of the deal supersede the success of the overall product or service or whatever it is we're doing. we're like, you know, that sunk cost fallacy. We're so far in, let's just get it closed. When in reality, sometimes the situation is telling you, no, you're not aligned. You didn't know it before, but now you know it really clearly. You're not aligned. Success might be actually stepping away from this deal as hard as it might be.
Cydni Tetro (48:18.096)
That's right.
Cydni Tetro (48:23.748)
Yeah. And those moments just exist for you. The more you are in your career, the more you have to decide how you'll show up with those. And you're going to find them all of the time. And some go well and some don't go well. And it's just going to be the nature of being willing to lead something.
Jeff Holman (48:38.68)
Well, so I'm curious then how, and I know you said you had two breakout moments, but I want to explore it at this topic just a little bit more. If we have time for the other, great. But, the, do you deal with that when things don't go, when you have to pull the plug? Cause as a leader, the initial shock is pretty terrible, right? You're, you're like, did I fail? Like this was supposed to work out. How do you take that and manage that, in your own role or personally even?
Cydni Tetro (49:00.014)
I'm done.
Cydni Tetro (49:08.164)
Yeah. I mean, I think that it's a very fair question because at least for me as a CEO or as a leader of an organization, I feel so personally, like success or failure of what I'm building and the people around me. It's just in my DNA for that to fill just so deeply in me. And so when it doesn't turn out right, you really do, are you like...
Jeff Holman (49:21.742)
Mm-hmm.
Cydni Tetro (49:31.428)
Kyle, those other people down the street don't look like they're failing. How come it's sitting on my shoulders? Like, am I not good enough? Do I not show up in the same way that they are? Am I not smart enough to be leading those? Those people seem to be way better. All of those questions, they do run through my mind in those situations. I had a situation where, again, I've had many of this and now I have too many of these stories, but I guess that's what happens when you build stuff. So I was fundraising. I had...
Jeff Holman (49:46.285)
Yeah.
Cydni Tetro (49:58.866)
a deal that blew up at the very, very last minute. I had been in a no-shop clause for like 45 days. So I hadn't been talking to other investors for money I needed in the business. And I had had a founder who exited who asked for something in the docs that just blew the deal up like three days before it was supposed to close. And we needed the cash. I had signed a major agreement with a national retailer. We were set to launch in six weeks. And I was like,
Oh my hell, what do I do? Like, I don't know like where to go. And I, and I remember cause I, and before that we'd been fundraising and I was in a category of fundraising. When you fundraise, everyone rejects you. So it's now been like six months where even though we got to a term sheet, like you're waking up every day, like someone's going to tell me they're not putting money into my company, which either means I'm a bad leader or my idea is bad or I didn't do the right deals or there's something in the ecosystem that I fundamentally should have done differently. And I remember a time period where I was like, I'm actually not looking
Jeff Holman (50:46.178)
Right, right.
Cydni Tetro (50:56.339)
my email until I get to the office. Like I'm not waking up in the morning and looking at it because it's too hard because it's so much rejection. Like 99 % of the people I talk to are rejecting me and that's the nature of raising capital and it sucks. And I had to find this place where I'm like, I don't know how this plays out, but I'm going to do, I'm going to play every card I know I can.
Jeff Holman (51:01.836)
Yeah.
Cydni Tetro (51:20.657)
every card I can imagine, everything that I can possibly do to potentially solve this. And I basically had to make that decision. So I had to do things like not look at an email in the morning, like just take a moment to breathe before I showed up, but then also just personally commit that.
I might fail here. This company might shut down. I might not be able to get to where I need to, but I'm still going to show up every day and I'm going to brainstorm every day and make every phone call possible to see if I can pull this off and if I can pull it off. Awesome. But no one, because I found myself in a place where many people would have just walked away. It was harder to keep going than it would have been just like, yep, tried my best done. Like hanging up the phone. I just wasn't willing to do that. And that's just kind of my personal commitment. And maybe sometimes my flaw around like, I'm just going to go try everything.
Jeff Holman (51:55.736)
Mm-hmm.
Cydni Tetro (52:06.899)
everything possible because I always believe there's an answer and I'm gonna go for it. And I threw a couple of Hail Marys at the very end of that after things blew up that ended up working out for the organization. I, so I had been in the fundraising boat, my term sheet like blows up three days before, I'm six weeks out.
Jeff Holman (52:18.198)
What do mean by that? did it work out?
Cydni Tetro (52:27.503)
I threw a hell Mary and I called the partner who, be honest, he and I had only had a couple of conversations previously and we ended up doing a deal in a week to like, to basically make it so that we could launch and integrate our companies and provide an entire pathway for something where if you had asked me two weeks before that, I'd been like, I don't even know what my options are, but I would like, willing to show up and make the calls.
Jeff Holman (52:52.046)
Yeah. What they do, is that desperation or is that innovation? do you, do you know what mean? Cause everybody finds themselves. Those are always the moments that precede the breakout moments. It's like, oh, we're going to sell the company. Oh wait, no, we're not. That's, you know, we just landed a deal or whatever, right?
Cydni Tetro (53:09.637)
Yes.
Yeah, when I was in the mix of, I think it's a little bit of both, but I also think it's a, it's the, have to decide what grit means to you and how much you're gonna, you're going to take on because.
you're still going to get rejected all of those same times in those last moments. And the only way that you're going to see if they play out is to make the call. I think oftentimes we just tell ourselves it won't work out or we did enough. And the question is, did you go as far as you possibly could? was the fact that you envisioned that it wasn't going to work out stopped you from making those calls a long way? Because that's often what happens too, is you're like, yeah, we just can't make it go, or I don't have that skill set.
I've never done that before. And you just ultimately realize that every person who had to solve a major problem had to do it for the first time. And so you gotta be willing to do it for the first time and take the risk and take the emotion that comes with it and the stress and say, you're just gonna go all in and however you learn or whatever happens from that, you're gonna be okay.
Jeff Holman (54:15.606)
You may have just answered the next question I had. was going to ask you, you know, for people who are not as far along as you haven't had the same experiences or maybe run into a new issue for the first time, right? What, what's some, what are some words of advice that you would give them as a CEO struggling, maybe feeling that they're, they're a little bit alone in this. They don't have partners in their employees or the investors and they got to figure it out. Everyone's looking to them, you know,
What would you say to those people that are coming down the same path but haven't seen as far down that path as you have?
Cydni Tetro (54:54.927)
No, I think I would say two things. One is every person that you see and deem as successful has had major failures along the way. They might just not be visible. And every person who's built something is doing it for the first time. So all the things where you feel about your inadequacies or the gaps that you have in your skill set, all those people have the same ones. They just decided to look at the fear and look at the inadequacies and show up and do it and figure it out along the way.
And that's the thing that you have to do. Take all the things that you don't know how to do. It's okay to be afraid, but it's not okay to not do the work. You just have to go for it. And you're gonna be wrong sometimes, you're gonna be right sometimes, things are not gonna go your way sometimes. And the thing that will happen is doors will open you didn't imagine along the way because of whatever that path takes you. You learned something, you grew something, and you tried. And that's far more than most people are willing to do. So you should do it every time.
Jeff Holman (55:53.388)
Yeah, I love that. I have a philosophy that I've shared with some people about. I think, you know, we all have those fears that something's not going to work out or that we're going to look dumb or that, you know, that we're going to fail somebody or something. And my philosophy, just to put it briefly, is that taking action is really the only true solution to fear because we fear stuff in the future, but as soon as you take those actions, you've turned the future into the present. You know what the result is, whether you like it or not, you know it. There's no
no longer even a basis for fear. You might fear something else, but you can't fear the stuff that you now know because it's done. You can maybe feel bad about the results or feel happy about the results, but you can't really feel fear for that anymore.
Cydni Tetro (56:30.834)
Okay.
Cydni Tetro (56:37.564)
That's right, exactly. You move past the anxiety into, I'm a big believer in activation. Just take action and it will give you answers that you need in order to figure out your next decision. And fear just holds you back from taking action.
Jeff Holman (56:50.798)
I love that. And it feels like you might have a saying around, I don't know, I'm just gonna project this, because it sounded like you were going here, but it sounded like you were gonna say something like, activation over anxiety, or something, we'll catch phrase like that. So.
Cydni Tetro (57:00.562)
I can also say that that would totally work along the way.
Jeff Holman (57:04.718)
Well, Sid, this has been fantastic. We're coming up on more time than I think you reserved for me and you've been so kind with your time and your insights. I really appreciate having you on the show. You really have done so many good things. And I started out by saying, I think you're a local legend, maybe because of your resume, right? But I wonder if part of that is, because you get asked to speak, you...
you help show up in places and you're volunteering for things and you get awards for things. And maybe it's not so much your impressive resume that's doing it. Maybe it's because there's that impact that you're creating along the way in addition to the impressive resume that you've got. So it's been a pleasure having you on the show. I'm really glad that you're sharing your thoughts with us today.
Cydni Tetro (57:53.202)
So I've very much enjoyed our conversation and all the directions it's taken. And yeah, and think you hope the same thing, right? You hope that you make a difference in the lives of people that you get to work with in the work that you do.
Jeff Holman (58:05.088)
Yes, if I could open up the curtains with the clients I've worked with and say, no, see, everybody's dealing with that. I just can't do that as an attorney with my clients. So instead we have this show. yeah. Well, thank you again for being on the show. It's been a real pleasure. And to our audience, thanks for joining us one more time. Remember you can go and subscribe to the show on Apple, Spotify, YouTube, whatever. And we love having you.
Cydni Tetro (58:18.49)
I like that. That's a good, that's a good option. It was awesome. Thank you.
Jeff Holman (58:34.318)
Love to hear your insights. If you want to join us as a guest or you have recommendations for future guests, please reach out and let us know. And we will see you again next time with another great guest. And thanks for joining us.
