The Art of Embracing Failure: Leadership Lessons from Wall Street to SaaS with Peter Bonney

Peter Bonney's fascinating journey from Wall Street hedge fund partner to SaaS founder reveals powerful leadership lessons that resonate across industries. With refreshing candor, Bonney explores how his perspective on leadership dramatically shifted when transitioning from the short-term, quarterly-focused world of investment management to the long-horizon strategic thinking required in building software companies.

The conversation delves into Bonney's most valuable leadership insights—particularly his self-awareness around delegation and team management. Rather than highlighting successes, he candidly discusses mistakes that shaped his approach, describing a "pendulum swing" in his leadership style. After recognizing his tendency to be too hands-off and reluctant to make personnel changes, he deliberately adopted the opposite approach in his current venture. This conscious counterbalancing has led to greater efficiency while allowing him to fully trust proven team members in critical areas.

Bonney's explanation of Software as a Service (SaaS) provides clarity for listeners unfamiliar with the technology, highlighting how cloud delivery revolutionized software access for businesses. But the real value comes from his practical wisdom about leadership challenges—the delicate balance between taking risks and exercising caution, knowing when to delegate versus handling responsibilities personally, and recognizing when something isn't working.

Most inspiring is Bonney's perspective on professional growth and resilience. At 47, he feels he's "just ramping up" rather than winding down, with decades of experience now converging to maximize his capabilities. His parting message resonates deeply: face failure, learn from it, and do better next time. We're all imperfect humans with room to grow. Take risks and make mistakes—you'll have plenty of opportunities to put those lessons into practice.

http://fastbreakrfp.com/

http://github.com/pbonney/

Sponsored by Nico Van de Venne CommV

Chapters

• 0:00 Introduction and Guest Background
• 5:04 Transitioning from Wall Street to SaaS
• 7:37 Software as a Service Explained
• 11:02 Leadership Differences Across Industries
• 16:11 Building vs Delegating: Leadership Challenges
• 27:07 The Pendulum Approach to Mistakes
• 32:36 Closing Thoughts and Key Takeaways

Transcript

Peter: 0:00

The whole experience that we've had professionally has been to face failure. Lean into the failure, learn from it and do better next time. That's all we can do. We're all imperfect humans. None of us comes out as fully formed. Learn from your mistakes, Make all the mistakes, Take risks. You've got lots of opportunity later to put your weapons into practice.

Nico: 0:35

Let me invite you to sit back, drop your jaw, tongue and shoulders, take a deep breath and, if you wish, close your eyes for a moment and feel the beat within.

Nico: 0:43

Close your eyes for a moment and feel the beat within In a few seconds. You just jumped from your head to your heart and felt the beat within opening up to receive even more value and fulfillment out of your business and life. And today's episode. I am your host, nico van de Venne, confidant to successful CEOs, founders and entrepreneurs who are striving to achieve everlasting fulfillment. Before we dive into today's episode, I have a small request. If you find value in our podcast, please take a moment to subscribe and leave a five-star review. Your feedback helps us reach more listeners and continue bringing your amazing content and amazing guests. Pair this episode with someone who could benefit from it and join our community of like-minded individuals on this journey with Velocity. Thank you for your support and let's get started Now.

Nico: 1:35

First, my introduction of our next guest, peter Bonney. Peter Bonney is the CEO and founder of Fastbreak, a B2B SaaS company that helps sales and pre-sales teams leverage the company's knowledge and collaborate seamlessly with internal subject matter experts to make complex deals faster and easier. Previously, peter was a CEO and co-founder of Vendorful, a SaaS platform focused on making complex procurement processes more efficient and transparent. Peter, you have a beautiful history, an interesting history and I am looking forward to you telling us who you are and go right ahead. I would say.

Peter: 2:20

Thank you very much, nico. I'm really happy to be here. Yeah, thank you very much, nico. I'mcom boom to about 2015. And I spent most of that time at a hedge fund. There for part of 13 years I was a partner and portfolio manager there. So I had a successful career before I decided to change careers and do something different, and so I think that might be also an interesting thing to get into, kind of going through that journey. But yeah, so I've been.

Peter: 3:11

You know, I got really interested late in my Wall Street career in the problem of how businesses actually engage in kind of like these complex commercial transactions and specifically how companies buy and sell things. Right, um, and this was partly for personal experience and watching portfolio companies struggle with having to make these multi-hundred million dollar investments in partners. Right, I'm not talking about acquiring a company, I'm talking about buying a service or a product. Engaging with a construction company for a massive mine project say, right, we're going to spend hundreds of millions of dollars. You know, if you're a small company and you've raised hundreds of millions of dollars to build a speculative mine, you're kind of betting your entire company on this one business relationship.

Peter: 4:01

It's a challenge to get it right. I saw a lot of companies get it wrong. Relationship. It's a challenge to get it right. I saw a lot of companies get it wrong and so I got very, very interested in those sorts of interactions and that's really what I've been focused on for the last nine years Now, with two different companies, sort of tackling the problem from two different sides.

Nico: 4:17

So let's jump back to your history there, where you were saying you're jumping from one career path to another one, because that's, you know, interesting to me. Um, I must say, um, if I'm listening what you're saying, you're a pretty high achieving, uh, individual. Um, you'll probably met some challenges along the way when transitioning from one thing to another. Could you, you know, deep dive a little bit on that?

Peter: 4:43

Yeah, well, you know what's interesting? I would say probably my entire career was a series of having to transition from one thing to another, even though I was in the same company. I was at this one fund for 13 years. I started, I knew nothing, I was the junior analyst on the desk and eventually became a partner and then ran a pretty large portfolio and then contracted to take over an even harder portfolio sort of post-financial crisis world. That whole time and really I think anyone who's working on Wall Street, particularly in investment management nothing is static. You've got to constantly be reinventing yourself. The strategy that was working really well, paying money you know last year, this year, might not work anymore, right? And so you know, over the course of my career, uh, in addition to sort of growing, progressing in my own knowledge and going from, you know, working for somebody else, then working for myself inside the company, I had to constantly be looking for new and different things to do that would actually be profitable going forward, because the past never repeats.

Peter: 5:58

Yeah, constant, constant process.

Nico: 6:03

Now, if you talk about Wall Street, I always this you know, the big bulls is the first thing things that comes to mind. Yeah, right, yeah, I spent some time in new york, uh, in a in a previous life. I would say, um, it's a very big hustle and bustle wall street.

Peter: 6:20

Oh, it's a subject.

Nico: 6:21

That goes on, on and on and on and I can imagine what you're saying. It switches constantly, but I see the same relation without the bull uh in it. So, especially when you're talking about sass, um, yes, you know, I've been 15 years in it myself. I was more a hardware kind of guy, engineer and and sport um, here, but um kind of quickly went into management, uh, in, in, in that perspective.

Nico: 6:50

but, um, now you're, you've gone from one hustle and bustle into another hustle and bustle, because, if you're talking about the dark dot com era, yeah, that was a time where the computers were, you know, becoming mainstream and it guys were, were exceptional, uh, people walking around in the office and everybody liked them because they fixed stuff. Now, going over to the cloud story, where SaaS becomes reality, let's first tell some of our listeners what SaaS stands for, because I think that might be interesting. We're talking abbreviations are something that I've lived with for my whole life, but a lot of people ask me so what do you mean?

Nico: 7:32

What's your take on SAS? Let's say that.

Peter: 7:34

Yeah. So SAS, for those who don't know, stands for software as a service, and the idea is that you have software that you know can run on your computer locally. Right, like you, back in the day, you would have, you know, microsoft Word or Microsoft Excel installed locally and maybe you still do, although even those are now very frequently cloud-based. But you know, you have your programs that you run on your computer locally, programs that you run on your computer locally. And then companies have programs, you know, business productivity software, which historically has been installed in servers on their premises, called on-premise software, and you know so. Something like SAP is a famous example. Or an Oracle database right, like a giant database that literally runs on internal servers that people inside the organization will access for programs and tasks. Now the Stas revolution sort of introduced this idea that you don't necessarily need to physically deliver software to a location, it doesn't need to operate in a specific data center inside your office or on your computer locally. You can access tools that you want to use for productivity over the internet, and so this kind of has a number of different effects. It overhead is much lower, there's nothing to install, you're just using a browser, and it means that the cross-platform compatibility is a lot easier. It doesn't matter if you're using a Mac or a PC. You can access Google Documents through the cloud, you can access Microsoft Excel through the cloud, and then everybody is able to operate on the same tools, whether or not they have the same IT setup. And then everybody sort of is able to kind of operate on the same tools, whether or not they have the same IT setup. And then on top of that, for companies, by accessing software like enterprise-level software through the cloud, they don't have to maintain the servers. Now they're obviously paying for that infrastructure to be provided by the SaaS company.

Peter: 9:46

One of the interesting things with cloud software people are discovering it's not necessarily cheaper. It is a different type of cost, right, depending on the type of organization. You may or may not want to service servers on-premise. We're a small company, we're entirely remote, we're classic startup. I don't want to be running physical servers, I want all of my software to come through the cloud. We get to, you know, 500, 1,000 people It'll probably be the same calculus. We've got to. Being like, 10,000 people with multiple physical large offices might be a different equation. But you know the answer is there for every company, but it provides a different delivery mechanism and distribution mechanism, which has opened up a lot of opportunities.

Nico: 10:30

Indeed, indeed. Yeah, SaaS is something that people don't even know that exists.

Peter: 10:33

They use daily we're actually using streaming now and it's a SaaS product.

Nico: 10:38

I don't have it running on my computer, so it's just wonderful that we can connect from across the ocean in our conversation with this system. That's the amazing part about it. Now you went from Wall Street to the IT world. Now you're transitioning there. What are the differences in leadership skills that you've encountered?

Peter: 11:01

Yeah, you know it's Wow, that's. I haven't really thought about that. There's so many that come to mind I would say. Interestingly, when I was at the hedge fund, I was involved in some of the business management of the company. That was sort of how we were structured Partners all got involved in the business of the whole organization, and not all firms operate that way. Sometimes they'll have kind of a, you know, a business management team and certain the partners are kind of focused on just investing, not getting involved in things. Hr and it and sort of infrastructure had some exposure through that. But it really is secondary.

Peter: 11:47

Like when you're an investment firm, your job is to make money for investors, right, and that is how you were judged. Um, you know, and you get up to, like this, the c-suite level, then you know a lot of your job isn't talking to investors and things like that, and I wasn't at that level. It was, you know that. So I rarely spoke to our investors directly. I was very, very focused on my little team running a portfolio and the day-to-day execution of doing that. So leadership was kind of very short term. I would say You're not sort of thinking within my seat. How are we planning for the next five years. It's like how are we planning for the next quarter? Yeah, like, like what you know, what investments are we making you know for you know a time horizon that we care. How am I explaining this guilt? Do I have the resources that I need? Fine, maybe thinking a year ahead, like, am I gonna need another intern? Do I need an analyst? Do I need to remake some personal changes? Um, but much shorter time scale. Running a software company, even an early stage one, is definitely much longer term. Like you have to think further ahead, you know, yes, you're still kind of putting out the daily fires like what do our customers need today? How are we going to deliver this feature in the next month? That sort of thing, but always with a mind to like okay, what choices are we making today? That could be problematic for us a year, two years down the road in terms of, you know, technical debt.

Peter: 13:26

The software building design decisions made the strategic direction of the company right. Like when you position a software product, uh, meaning you decide, like you know, fine, I've got a product, I could try to sell it to, you know, different sets of people and that's going to involve maybe packaging it up in different ways, like how do we talk about it? What features do we focus on? Who do we try to you know reach to talk about it with. Those decisions have impacts a year, two years down the road, right, like you position your company and like we are focused on the health insurance space and we are trying to sell to those people, well, that's going to mean that your website is not probably filled with content to target IT people or other SaaS companies, and so all of that has an impact on how people find you, how you rank in Google, and it's all very, very long-term, long-tail stuff.

Nico: 14:26

So, yeah, there's a clear difference in what position you're rolling the dice. I would say Because what I've noticed I used to work for big corporations like Verizon and IBM and the things they were saying about the quarterly view was very prevalent there as well.

Nico: 14:44

So the levels that we were working, even in our projects, was that the project has an end date, supposedly.

Nico: 14:51

You know that the deadlines are made to be broken, as they say right, there was no, there was no problem right there to do that.

Nico: 14:57

But uh, I think a lot of companies have that issue. But but, leadership wise, if what I'm what I'm hearing is, if you look like at the following quarter, it does limit your opportunity as a leader to create a certain vision and strategy for the team that you're managing, because it's just a day-to-day putting out fires, getting stuff done, making the quotas that are out there, stuff done, making the quotas that are out there. What you're saying is, at your current position, you're actually thinking a lot further than that quarter and it also means that your team needs to know where you're going. Now, what I've noticed in the past is there's a lot of C-level people that have that strategic view and then they're like, okay, we need XYZ person to fulfill that view or that strategy or vision and they kind of stumble at that point to become so involved with the people that they hire that they get the experts in, but they don't let the experts be experts. Is that something that you've experienced in the past?

Peter: 16:20

Yeah, I would say that's interesting. I try not. I'm not trying to, uh, you know, over over over compliment myself here.

Peter: 16:32

I don't know if that's something yeah so my, because my approach to many people. I think this introduces different blind spots, uh, but not that particular one. I really I don't like to micromanage people. I really don't. If anything, I definitely err on the side of under managing. I think that is a weakness of mine.

Peter: 16:58

I've tended to focus a lot on hiring somebody that I trust for a role, giving them as much context as I can and then letting them own their domain and letting them run with what they need to and giving them the resources that they need to do it.

Peter: 17:15

Now, like I said, it's not to say that that makes me, you know, better than anybody else, because I think, if anything, I've run into situations where I've been sort of too much too reliant on their ability to execute, too trusting, too hands-off, where if I had intervened a little sooner, if I'd been a little bit more in the details of what they were doing, how they were running their domain, I might have corrected problems earlier and identified situations where we needed to change course earlier. Um, I think you know I've, I have, uh, one of the things people talk about is, um, that you don't want to decide, that you've, like, you've waited too long to change. You know change. You know change person in a seat you don't want to. Better to fire somebody early than late, and I have tended to here on the side, fire people too late, so that's been a challenge of mine to deal with.

Nico: 18:25

You're talking about this as if you actually noticed the issue very clearly. What? What triggers that for you? Because you'll probably have a trigger somewhere, somewhere that that says should have done this earlier. What triggered it?

Peter: 18:39

yeah, so you know it's. It's always obvious. In hindsight I would say, oh yeah, where you know somebody leaves the organization and you're like oh man yeah, you know what, like I didn't need them.

Peter: 18:57

Or you know, things are now operating a little bit more smoothly, um, or you know, okay, well, let me give a concrete example. Um, very, very first head of sales in my last company, vendorful, I would say that my co-founder and I made the classic startup mistake of trying to get out of founder-led sales too soon. You know, we sort of thought, like, okay, we've got enough of a process, we can hand this off to a professional and they're going to do a better job of it than we are. And that wasn't really the case. We didn't have enough process yet. Um, we, we didn't, we weren't in a position where somebody really could come in, sort of without having been around the company, you know, for a long time, and just sort of succeed because everything was in place for them. So, you know, we lost, frankly, several deals, um, because we ignored, uh, our own instinct for how to pursue things and sort of said you know what, hey, what, this is his, his domain, he is a professional salesperson. We are not, we're gonna trust him and not only are're gonna trust him, like we're gonna let him take that risk right. That like that's what we need to do as leaders. We gotta let him spread his wings and either fly or fall. Um, which is fine in a sense.

Peter: 20:22

But when you're at an early stage, startup, and you're a leader of that company, those kinds of decisions, those kinds of failures, have a lot of knock-on consequences. Right like, look, if you've got, you're sitting at a hundred million dollars of revenue and you lose two thousand dollar deal, it's not the end of the world. You're sitting at half a million dollars of revenue and you lose a $200,000 deal. That is a real impact on your future. And so it was obvious in hindsight from how a certain deal progressed and how at the time it was not just hindsight. We were co-founder and I were discussing amongst ourselves I think we should do this differently. But we're gonna, we're gonna follow, we're just, you know, we're gonna follow his lead. And then, you know, once we made the change and we were back to meeting sales ourselves again, we're like wait, you know, this, we're, this is more comfortable, we're more comfortable with how this is going, it's going better. And so that's on us for not recognizing earlier that it wasn't working.

Nico: 21:37

So did you take that experience with you into? Your new environment and apply it a lot quicker? Or was there less of a trigger to use it again? Because if you're saying that sometimes you still don't take that decision quickly, what, for you, is now the limit of actually firing somebody?

Peter: 22:01

Well. So I'm trying to approach it differently, because I'm sort of aware of this issue I have, and I'm sort of aware of this issue I have and I am. I'm sort of taking almost the opposite approach, where I am, against my instinct, maybe holding on to a lot more things myself and instead of thinking can I hand this off, I'm asking do I need to hand this off? Right, like, if I don't hand this off, is it not going to happen? So, and that has led, honestly, to me holding on to a lot more things and doing a lot more stuff myself, a lot longer than we did with my last company, and it has forced me to get more efficient, with the consequence that I'm finding, actually, I haven't needed as much support for certain tasks like marketing and sales as I thought I did the first time around, and I'm sort of like just setting the horizon further in the distance, right that, like you know, I'm I'm. You know, before I was thinking like, okay, whenever we, you know, once we get like a few benchmark nameplate customers, like we should hire a salesperson, now I'm thinking like no, I'm going to hire a salesperson. Now I'm thinking like, no, I'm going to hire a salesperson when I am so busy with sales that I'm losing opportunities because I can't I literally can't follow up. That's going to be my benchmark for when I need to hire a salesperson Now.

Peter: 23:32

I think one benefit has been that I'm less because I'm having to be so focused on those things that before I was like I got to hand this off, hand this off. I'm so focused on those things that I'm not involved in as involved in the jobs where I do have somebody that's working really really well, right, like our lead engineer. I've now worked with two different companies. In the jobs where I do have somebody that's working really really well, right, like our read engineer, um, I've now worked with two different companies going great.

Peter: 24:03

I have a tremendous amount of trust in him and, whereas my last company, I got a little bit involved in coding and managing the ins and outs of the product. I'm, you know, really managing the product at a much like higher level now, um, sort of major decision about what are we going to build, and not getting involved at all in any technical decision, how we build it, uh and uh. So I think it made him operate more efficiently and his team operate more efficiently. So it's been, it's been a benefit all around. But I mean to go back to your question like I've not had to let go of anybody because I've been much, much more cautious about hiring anybody until I know that, like I absolutely must hire someone, Does that make sense?

Nico: 24:53

Yeah, it absolutely does. Is this a point where you might say it kind of reversed the whole story, where before you were, you know, lag the dirty apple and, you know, throw it into the bin? Um, I'm very radical in in those decisions, but my team leads are, you know. You know we'll try this first and then then that while I'm like, listen, there is an issue, it's very clearly there. But these people also, you know it's been a hard time to get them on board anyways. You know, just find somebody to do the job was not easy, sort of like you know. But we have them now we're going to try it anyway and after like two or three tries, I'm like sorry, you get two opportunities and if you fuck up those two pardon my French it is just the end.

Nico: 25:55

Or we shift you to somebody else where you might feel much better, but that also, you know it's pretty extreme how I do it, but what I'm hearing is that you kind of shift to another point where you just become very cautious of even hiring somebody who could do a certain job and that you are actually managing a lot of or putting a lot of energy in a point where somebody else could do it. I perfectly understand, of course, and it's it's amazing what you're saying, that you're actually releasing the other part, where you're sure it's fine, those guys are doing a great job and and you're just really enjoying what happens there. Of course, it's your business, so I'm very happy for you. It's's your engineering part. That's fine.

Nico: 26:36

But it's something that I did notice in the past as well is where, at some point, leadership is becoming a risk-oriented story where you just have to say, hey, you know what, I don't always have time to do these things, so let's try to put somebody there who has potential. You know they have the right mental attitude. They might not have 100% skills, but you know you can guide them. Of course, it takes time for you as well. Yes, it's not a give or take, it's. It's a give. You know it's. It's very different. Is that something that you're you're thinking about, or how does that run in yours?

Peter: 27:14

it is. Yeah, I, I mean I, I definitely. I know that. Look you, you didn't explain it exactly this way, but the way I'm thinking about it all the time, uh, just broadly speaking, leadership aside, just decisions. I've made that, like you know, like, all I can think about for my last business is the things that went wrong. There were a lot of things that went right as well. Right, uh, you know we exited the business. You know it did okay. Um, uh, it was fine. A lot of things went right. All I can think about, honestly, it's just the mistakes I made, the things that went wrong. And like the pendulum is over here I am now swinging the pendulum consciously totally the other way as much as possible. I'm just trying to be aware of my personal biases and the way that I tend to behave and the mistakes I've made in the past and say I'm gonna for lack of any better way to approach it, I'm gonna do the exact opposite this time, until I find that I am wrong there as well, and then I'll try to modulate and the right spot in the

Peter: 28:16

middle, so that has led to me doing, in startup speak, a lot of things that don't scale. However, I am thinking about, as you said you got, you do have to be thinking about risk all the time, like what risks am I taking if I'm the person in charge of marketing, whereas before I had a marketing person? I'm the person in charge of sales, whereas before I had a marketing person. I'm the person in charge of sales, whereas before I had a dedicated sales person or sales team. That's all well and good in terms of not having to worry about having the wrong personnel, although maybe I'm not the right person, but I am taking risks.

Peter: 28:55

There's things that are not getting done or maybe not getting done as well as they could be or should be. I have to constantly be checking myself on. I'm trying to balance, basically, the risk that we invest too much in the wrong person or the wrong technology, whatever it is. It's not just people, it's any, any kind of investment that you make. Um, the wrong, you know marketing strategy, uh, against you know, the risk that I miss an opportunity.

Peter: 29:29

Right now feels like we are okay on the opportunities, and so I'm just pursuing them as best I can and trying to improve myself as well, like recognizing I'm not a tremendously I'm not. I'm not a top tier salesperson. If I can get myself up to like being, you know, a slightly above average salesperson, then, combined with being the person who knows, you know everything about the company and, frankly, can direct things like we have a. You know, one of the privileges of being a founder who's leading sales is that when an opportunity comes along, somebody needs a new feature in order to execute. I can make the decision like, yeah, we're going to build that. Um, yeah, and a you know, sort of a higher salesperson doesn't really have that privilege. Um, so you know, it can make up for a lack of skill. So, yeah, look, opportunity cost the risk. Every decision you take has a risk.

Nico: 30:24

You have to be thinking about it, thinking about what you're leaving on the table, and just do the best you can story as well that I, you know, message that wants to get out there is realize that you're doing your the best you can with the information and situation that you're in right now, even at the level of higher management, c level or whatever, or founder, you're just, you know, rolling the dice each day and and realizing that there might be a wrong dice in there.

Nico: 30:55

It's as simple as that. But I do hear you say very clearly that self-awareness is very important right there. So it's it's amazing to hear that way that you brought it up where pendulum, you know where you can throw it one side to the other very consciously, it can save your business. You know a lot of problems in the end, even if you take less, of course, absolutely it's amazing what you've been doing, peter, and I think people might get a little bit of a trigger to hear more from you or read more from you. Where can they find you? How can they contact you?

Peter: 31:39

The easiest way to find me is on linkedin. I'm easy to find there. Just search for my name. Uh, I should be one of the the few peter bonnies who comes up. Uh, and yeah, I'm pretty active on linkedin, I I will uh share random thoughts from time to time about leadership, about technology, about AI, about startup life, about I think the most popular post I ever had was actually about conference leaders Random, yeah. So find me on LinkedIn and that's where you should go.

Nico: 32:14

Nice. Is there any message that you want to put out there that might inspire a leader, aspiring, current leader or whoever that you really want to put out there?

Peter: 32:28

The whole experience that I've had professionally has been to face failure, lean into the failure, learn from from it and do better next time. And you know, that's all we can do. Uh, we're all imperfect humans. None of us comes out as fully formed. I'm now 47, going on 48. You know I don't feel like I'm winding down, I feel like I'm just ramping up, that, like the, you know the, the 25 plus years experience I have professionally is starting to like really really sink in and and and maximize my, my capabilities. And so, you know, just keep learning, keep growing, learn from your mistakes, make all the mistakes, take risks. You've got lots of opportunity later to put your lessons into practice.

Nico: 33:22

That's a really great message. Thank you so much, Peter. Thank you for being on the show.

Peter: 33:27

It's been a wonderful conversation, a couple of nice insights.

Nico: 33:29

I must say that's been great.

Peter: 33:32

I really appreciate it, Nico. This was a lot of fun Super.

Nico: 33:36

And to our listeners. Thank you very much again to listen to another episode of the Everlasting Fulfillment Podcast. Have a great one everybody.