The Diary of a CFO · 2026-03-26 · 38 min
Key moments - from our scoring
Substance score
63 / 100
Five dimensions, 20 points each
Julianne Averill brings deep expertise from scaling companies (including CalIndex from 13 employees to the largest healthcare IT company in the US) and now works as a fractional CFO advising biotech and life sciences founders. The episode unpacks how founders should translate ambitious visions into realistic financial plans, particularly in capital-intensive industries with long development cycles. Averill outlines the funding journey from Series A (betting on founder execution) through Series B (proof of concept) to Series C and beyond (de-risking and scaling), and emphasizes that founders commonly make three critical errors: over-focusing on product/science while neglecting operations and business infrastructure, partnering with misaligned investors (e.g., tech investors for biotech), and underestimating the need for strategic financial guidance early. She explains how to structure finance teams appropriately at each stage - from controllers and bookkeepers at seed to fractional CFOs providing strategic oversight - and why treating finance as a cost center rather than a value driver is false economy. The discussion also touches on the realities of going public (not an endpoint but a new chapter requiring external-facing finance and quarterly rigor) versus M&A routes, and how debt and equipment financing can extend runway when equity is raised.
Founders often focus too narrowly on building only their science or product while neglecting operations and business infrastructure, and they sometimes pursue funding from investors misaligned with their mission (e.g., tech investors for biotech). The result is under-de-risked companies that struggle to execute against investor expectations.
Early-stage companies (seed to Series A) benefit most from a fractional CFO who provides strategic guidance on milestones, debt/equity decisions, and capital planning, paired with a full-time controller handling day-to-day bookkeeping and accounting. Once a company uses finance expertise 40+ hours per week, that's the signal to hire full-time.
Funding rounds are sized based on development phase and milestones; early-stage rounds emphasize founder, team, and scientific potential; later rounds require proof of concept, built-out teams, and de-risked assets. Strategic planning around debt (equipment loans), equity timing, and runway extension through each phase is critical.
IPO makes sense if the company has operational infrastructure for public reporting, upcoming milestones each quarter, and an executive team ready for external scrutiny. M&A (merger of equals or strategic fit with a larger portfolio) is better if there's complementary product fit or if a larger acquirer can better realize the company's long-term vision.
A strategic CFO understands the full business (revenue drivers, product development, key milestones) and partners with the CEO and board on capital strategy, investor alignment, and long-term planning, whereas a controller manages day-to-day accounting and compliance; together they transition finance from a cost center to a business value driver.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains solid operational frameworks (funding round structures, M&A considerations, finance team scaling) and some useful specifics (5-slide pitch decks, lockup agreements, data room importance), but relies heavily on broad principles and repeats common CFO talking points without sufficiently dense novel insights. The conversation covers familiar territory - vision alignment, de-risking for investors, internal controls - without enough concrete, non-obvious guidance per minute.
it's either you pay now or you pay later. So the way to think about it is it's like deferred maintenance on your car.
make sure our pitch is on point and then also always make sure your data room is clean and truly tells your story of the company
The episode draws heavily on standard CFO playbooks and well-established venture capital conventions (Series A/B/C definitions, IPO readiness checklists, M&A integration issues). While the guest offers personal war stories and some valuable framing (e.g., the AI venture fund anecdote, the 'fingers in, fingers out' board principle), these feel more like illustrative examples than contrarian or first-principles thinking. The frameworks presented are conventional wisdom for the finance community.
Series A is really idea. So it's your, you're betting on the founder and can they execute?
It's not the end state. It's the start of a new wave.
Julianne Averill is a credible operator with 20+ years in finance, fractional CFO experience across multiple life sciences companies, and genuine M&A/IPO exposure (50+ deals claimed, though not all verified in transcript). She has board-level experience and has navigated the full lifecycle from startup to IPO. However, she is not a household-name founder or CEO, and much of her credibility rests on life sciences specialization rather than broad B2B applicability. Her experience is legitimate but somewhat narrow in scope.
I've been through over 50 in my career
I was employee number 13. So I was doing, it was awesome...we scaled from this little tiny startup of 13 people to we became the largest healthcare information technology company in the entire US
The episode includes some concrete examples - the AI venture fund with algorithm-driven investment decisions, a specific M&A war story about a 40-person company, mention of equipment loans as debt leverage, the 5-slide pitch framework - but lacks hard numbers, named companies (except 'CalIndex' and vague references), timelines, and dollar figures that would make advice actionable. Most claims remain at the principle level ('bring on expertise when you need it', 'align with investors') without sufficient granular data to test or replicate.
a Series A, but has raised $300 million and plans to go IPO a year from now
their entire process was done by AI...they gave you a score and then they say yes or no
The host asks reasonably structured questions and attempts follow-ups, but rarely pushes back on claims or probes for deeper contradiction. Questions are often open-ended invitation for storytelling rather than sharp probes. When the guest mentions 50+ M&A deals, the host doesn't ask for calibration or specifics. The host is courteous and enables flow but lacks the aggressive follow-up or productive skepticism needed to deepen substance. Several softball moments ('That is so cute') signal lighter interviewing.
I'm curious to hear your stories, especially around the buy side versus the sell side. Like what are the things you probably learned the hard way
I'm always looking for stories, right? Is there any set out story from your time as a CFO
Computed from the transcript - who did the talking, and the words that came up most.
Most founders make the same fundraising mistakes and do not realize it until the cash is gone. In this episode, I sit down with Julianne Averill, a healthcare AI CFO, board director, and fractional CFO with over 20 years of experience helping life science and digital health companies scale through fundraising, M&A, and IPOs. She has been through over 50 transactions on both the buy and sell side and currently serves as a fractional CFO working with multiple founders. We break down how startup funding actually works from Seed all the way to IPO. What investors are really looking for at each stage. The difference between debt and equity and why getting that wrong can be one of the most expensive decisions a founder makes. The 9 mistakes she sees founders make during fundraising that kill deals before they start. What actually happens when a company goes public and why it is not the finish line most people think it is. How AI is changing the way investors discover and evaluate companies. And the ideal finance team structure as a company scales. Whether you are raising capital, sitting on a board, or leading finance at a growing company, this episode covers the full picture.
Transcribed and scored by The B2B Podcast Index.
Welcome back to the Diary of a CFO podcast. I'm your host with Wassia Kamon. Each week we explore how top finance leaders help build high performing teams, partner with CEOs and boards and lead through growth and transformation without burning out in the process. Today's guest is Julianne Averill a healthcare AI CFO and board director with more than 20 years of experience.
She serves on public and not -for -profit boards, chairs audit committees, and works with founders and executives on how to use AI thoughtfully in their businesses. So glad to have you on the show. Welcome, Jillian. I'm so glad to be here.
Thank you for having me. Of course. Of course. I was always curious, you know, when I got to learn more about you, to understand how did you end up in the world of live science and biotech, especially as a CFO?
Yeah, well that's a great question. It was one of those things where it was, I'd say slowly and then suddenly. So I started out in finance with an interest in numbers and then grew up, my parents were in the medical field. And so I'd always been that person who'd been exposed to the numbers, exposed to the health side of everything.
And then about actually 10 years ago now, I had the opportunity to work for a healthcare information technology startup, CalIndex. And it was able to be, I was employee number 13. So I was doing, it was awesome. I was doing everything from HR to finance to basically all the operations.
And we scaled from this little tiny startup of 13 people to we became the largest healthcare information technology company in the entire US. So that was my really first biotech health tech company. And then kind of went from there and have been in life sciences ever since. Wow.
And so at which point did you actually became a CFO? Cause I know now you're a fractional CFO. So I'm curious to hear your journey to first become CFO and then the one to become fractional CFO. Yeah, I know that's a great question.
So how I became CFO was I started out initially in public accounting. So prior to the health IT company, I had to start in forensic accounting, interestingly enough. So really I was helping companies figure out like when things went wrong, why did it go wrong? And then I did the public accounting journey.
So really helping companies figure out like their internal controls and all of that. And then went in -house. So I was at the health IT company. And then over time, my journey just took off as the companies I was at, we would go through mergers and growth and all of that.
And so as I got more responsibilities, I moved up successfully. So I started at that company as a controller and moved into the VP finance role as I took on the finance side. And then eventually I moved into a biotech company that was actually using AI to develop drugs to treat depression. And then that was kind of my first CFO role because I was the one running the finance side of the house.
And then from there, then I moved into a CFO role during COVID. So for a company that was developing a at -home infectious disease test. And then at that point, Since I've done so many of these companies where you're running the show, the company I'm at currently approached me and said, wow, since you've done all this work with companies that have done acquisitions have really gotten like, for example, that biotech company I was at, we prep for IPO. They're like, how about you come and be a full -time CFO for a bunch of fractional companies.
That was five years ago. And I've done that ever since. Oh, wow. So when you went fractional, when you first got, you went to that fractional role, what surprised you the most?
You know what surprised me the most? was two things. It's one, it was learning how to let go from you're basically an advisor. So you have that differentiation between being an owner, like when you're in health, you really want to say to the CEO, like, hey, this is what we need to do and then go fully execute.
Whereas with an advisor, you are executing, but at some point you have to say, okay, if that... CEO wants to do something and it may be something that you disagree with, you can tell them, hey, here's what you should do. But if they still go do it, you let them go do it. And then the second thing I found was when I joined the current company I'm at, it was 2021.
So we were still in the middle of the pandemic and we were starting to see a shift in life sciences. So we're starting to see a lot of that downturn. And what I found was as companies would struggle with funding, oftentimes you'd advise them like, Hey, if you don't think about these three or four things to fund your business, you're probably going to run out of cash before you get to accomplish what you want to do. Whether it's to bring your great drug to market, whether it's to achieve your next fundraising milestone or something like that.
And I was amazed that oftentimes they wouldn't think about how they take that fuel, which is that cash or that funding, and be able to really see it through and ultimately would run out of cash. Wow. And so as a fractional CFO, you work with a lot of founders now. I'm curious to hear when founders come to you with a big vision, always have big vision, say our CEOs, how do you help them translate that into a financial plan that can actually support it?
Cause like you said, you can have a big plan, but be short on their balance sheet, especially when it comes to cash. So how do you walk them through that journey? It's a great question. So how I walk them through that journey and it can be oftentimes they're coming to us and myself and maybe a team, it's really understanding where they want to end up.
So they may give me a call and they may say they want to go IPO tomorrow, which is like, okay, well that may or may not happen, but we can try. Or they may be ultimately looking to be. acquired and be part of a larger pharma someday. But it's really working with that partner or CEO founder to understand what their ultimate vision is.
So where do they want their company to go? And how do they want their technology or their therapeutic to live on? So are they taking it all the way like with us in development, we have different phases. So we have like that ideation phase, we have that development phase, like does it go through clinical trials oftentimes?
And then we have that commercial And so I partner with them to see, okay, how far do they want to take this business? And then we kind of work backwards from there to develop that basically that long -term strategy and those financial models that can support them through that fundraising process. Okay. And so when you come in and you, like you said, I think in life sciences, the life cycle is quite long, right?
Cause I used to work for a pharma company as well. Um, so how are you able to say to these businesses that have this kind of long life cycle, how do you keep cashing? your bank account? How do you get funded?
Yeah, so it's interesting because oftentimes these companies may have no revenue or maybe early stage revenue. So a lot of it is founded almost on it's really understanding that valuation and that potential. And so what we're thinking through in terms of funding rounds is it depends on where they are in that development cycle. And so, for example, if they're very early stage, so they're really at that, okay, we're thinking about this idea where we have the science, but we don't have, okay, it hasn't gone through clinical development.
We may not have gone through human proof of concept data. It's really showing the investors what they have available. So at that point it's the people, it's the early stage potential from any scientific studies they have, but it's really that long -term potential to see could this eventually become a drug that could help people. Then if they're later stage, and like let's say they're looking to go to the public markets, it's have they taken...
whatever they developed and significantly do you risk it. Plus they've also have a built out the business to really be a standalone public company that can basically turn out different milestones quarterly, annually, and have a team that can really partner externally and build out that public company infrastructure. Okay. So now let's bring it back to just any company trying to go from where they are now.
So that IDH and process all the way to IPO. Can you walk us through how that's. out of funding works from series A, B, all the way, all the way. I'd love to be a private company at Z.
That'd be amazing. So really when you think about it, it's, and cause I know that the A, B, C and all that kind of starts to get muddy nowadays. A is really idea. So it's your, you're betting on the founder.
You're betting on the founder and can they execute? So what do they have? Do they have a great product? Do they have a great team?
Towards B, you're thinking about proof of concept. So have they started to build out the team? Have they started to get traction? So like if they have a product or service, do they have a minimum viable product or do they have early sales if they're a revenue generating company?
By the time you get towards C, and this is kind of where it gets muddled because you could be B1, B2, C2, blah, blah, blah. But that is really about have you started to D. risk your asset, build out your team, and also have you start to build out the business to take you to that next stage. And the next stage can be again, the E to Fs or even the public market.
So really are you able to scale and have consistent robust milestones or maybe you have more assets, more service lines, more segments and things like that. So it's kind of the way to think about it, basically that growth trajectory. And oftentimes investors are really looking for that billion dollar company. So what is it that's unique about the team, about the founder that's really going to take you from point A all the way up to that trajectory and that scale.
And so as the companies are moving through these rounds, how do you help founders figure out whether debt or equity is a better choice? That is a great question on that perspective because it's really all about how do you found that company and how do you add that fuel to really get your company through to realize your vision? And so it's pulling those levers to say what is it that can extend your runway? And then also how do you think through what makes sense for the company long term?
So when we think about debt, debt is always a good lever when a company company has additional capital. So like if it has equity with debt, then that means what debt can do is it can really enhance the company. Or oftentimes a lot of the companies I partner with, if they're very capital intensive, debt may be a good lever. So for example, equipment loans to really help find a way to leverage and extend the runway because you take out an equipment loan and then you can really think through, okay, I can use like my equity funding to then extend my runway and focus on the development side, whereas the debt is focused on the equipment.
And so at which point would you say, especially for the founders that come to you when they're like, okay, I'm just calling you, I'm stressed out. What would you say are the biggest mistakes you see founders make during these fundraising rounds? Yeah. So it's when they call us and they're stressed out, it's, it's when they start to think too narrow and then they start to say, okay, I don't need X, Y, and Z.
And by, I mean, X, Y, and Z. I mean, like, for example, if we're at mid stage, they forgo building the operation. and they focus exclusively on building just their science or their asset or their technology. Because the thing they always want to keep in mind is if they want to be a standalone company, how do you de -risk the full picture for investors?
But also more importantly, where do they want to be as a company overall for themselves? And also talking to those investors that make sense to partner with them as well. because sometimes I see a mistake is they'll go for example a biotech may be talking to a tech investor that may not be fully aligned with their mission and vision. And then if they get funding from that tech investor, that may not work or vice versa, you know?
So it's always making sure that you have the right funding from somebody who really aligns with your vision and vice versa. Okay. I'm always curious to hear, especially when it comes to cash management and building a sustainable business. Most founders don't have a background in finance.
So what has been some advice or go -to moves you've done? to bring them along with you all the way. Because like you said, they may choose to say, I don't want XYZ, but you as a finance person, you know that XYZ is needed, whether it's for your investor relationship or just having enough runway to make it till the end. So what have been your go -to moves?
Yeah. So my go -to moves are really to bring them along in the process. It's meaning that founder where they're at and then helping educate them in a way that makes sense for that person and that person's personality. And what I mean by that is sometimes if you have a founder that's early stage at a seed stage, they may not necessarily need a high power CFO.
They may want a controller or head of finance who can be that day -to -day partner and can really get the tactical work done and really partner with them from that perspective. But then my role as a fractional CFO is to really be that strategic thought partner to them to check in with them periodically and see, okay, are you thinking about your next milestone or your next development process? And then really be there to answer any questions. It can be anything as simple as, okay, what should your monthly burn be for a company at this stage?
So it's really being there to be their sounding board about these questions that will come up that they may be getting from investors on the finance side and help them think through those strategic items. Okay. I would like to pause a little bit here on the ideal finance structure as a company scales, right? We thinking, like you said, you start up maybe need a bookkeeper or controller, but you probably see also new fractional CFOs.
So can you walk us a bit through how do funders can realize or other finance people realize when to grow the finance and accounting function and how, like which roles do you bring in at which point? That's a fantastic question because one of the things you want to do is you never want to, and this is for any role, is scale too early. And so the way to think about it, and this is probably due reason we have such a growth in fractional roles or even the reason my now exist is bring on the expertise when you need it and leverage consultants i .
e. the fractional roles until you get to that point of okay you're using somebody 40 hours or more per week and specifically to your question about what do the teams look like at each stage it can be slightly different depending on the company so if you have a small company where they just have us operations and they're very simple maybe they're pre -revenue and their burn is a million dollars a month They may not need a very large team at the beginning, but then when they go public, they may need to supplement with additional technical resources, bring on the CFO, all of that, versus a early stage company that's technically a Series A, but has raised $300 million and plans to go IPO a year from now.
That may need a bigger team. So the way to think about it is in terms of scale and in terms of complexity from the business operations too. Okay. When you think about the actual talent, so we agree on you need a controller.
Um, but then who else do you need? Because at some point we have to think about internal controls. And once you go public, you want to build that structure before you go public. But unfortunately, a lot of people see accounting as a cost.
Finance as you guys are too expensive. What are you doing? So what are your thoughts on that? My thoughts on that are it's either you pay now or you pay later.
So the way to think about it is it's like deferred maintenance. on your car. So it's you can do your oil changes or you can wait till the catalytic converter blows up and then go fix it all at once. And so this is where the leverage of like a fractional model becomes really important is if you bring on strategic resources early, so like a strategic CFO, even strategic legal or ops, those are good resources to supplement even at a few hours a month because they can help you think through, okay, what are those roadblocks that you may be missing?
And so that's the thing to think about is that I know I see a lot of founders sometimes forget is they'll say, okay, I want a controller now and I'll keep me running for a few years. And then they may find out the hard way that, okay, I should have been back to the debtor equity question. Maybe I could have been thinking about bringing on debt when I'm closing my round. And that's what a strategic CFO can really help them with because they tend to have the connections to the different lenders and think about the different sources of capital.
Now I like how you keep saying strategic CFO. So I'm curious to hear what's your definition of strategic CFO. And as you think about the life cycle of a company, the maturity stages of the company, what kind of CFO do companies need at each stage? Yeah.
So my definition of a strategic CFO is a CFO who understands the business and is really a partner to the CEO, the executive team, and the board. And that's regardless of industry. So it's somebody who really understands how the business runs. So what are the key drivers of revenue?
If the company has revenue or the product development. So like in biotech, oftentimes we're pre -revenue. So you really need to understand that at the CFO level. And then even down into the lower levels too, for finance.
So every single team member of finance and operations should really be those partners to the rest of the business. how that's how we end up transitioning from what we're reviewed as a cost center to more of a partner. for the rest of the business value driver. Okay.
And then as the company mature, so part of the startup stage, what are the kind of skills that founders or CFO may want to bring in? Because how you run a business when it's just scaling or pre -revenue is definitely different than when you are or you pass the startup stage. Now you have, let's say quality compliance to be done and all that other good stuff. Yeah.
So the, the skillsets to bring in beyond that stage. So really the growth stage in the public stage are in. who are very familiar with internal controls and then additionally Individuals who are familiar with leveraging technology to build segregation of duties and compliance. So really to make it easy for the business to get greater insights faster.
And what I mean by that is like, for example, we're starting to see a lot of growth with artificial intelligence being able to give us financial data sooner, but really you need individuals who can understand how to weigh the pros and cons of what type of technology to implement. So that way you can give your business partners, so like your manufacturing team or your commercial team data that they can use to make decisions. And that's really important. And then of course, when you go public, you really need to make sure you have your technical team either outsourced or in -house so that way you can deal with your SEC compliance requirements as well.
Oh, let's talk about that part because you do that a lot. What are some of the things you will say you wish people knew about going public? Because when we hear a company going public, everybody's thinking mula money coming in. But what are the realities of transitioning from the startup stage to becoming a public company?
The biggest reality is it's not the end state. It's the start of a new wave. And so that's the piece that I think is always an evolution for a lot of individuals to understand. And that is a big transition for a lot of companies, especially when it happens very fast, because all of a sudden finance goes from more of an internal function to the, it becomes a very external facing organization, where you're partnering even more so with your CEO, with your teams and even, I mean, the CFO is directly talking oftentimes to analysts, to bankers and everything to say, okay, here's what's going on with the company.
And then more importantly, everyone in the company starts to learn whatever you say out there can actually impact, you have a stock price and that can impact things. And a lot of individuals who have been in just the private company world may not understand that. So it's a, it's a mind. And it's a good fun mind shift, but it's also just, okay, you go IPO and you're not done.
It's your starting and it literally starts from day one and you hit the ground running. And basically depending on when you go IPO, it can be three months after that your queues out or it can be who knows two weeks after that. So it just depends on what day you pick to go public. Okay.
And what would you say is the right thing to do when a company should stay private versus going through a public. offering. It really depends on what the objectives are of the company long term. We are starting to see a lot of this trend come back, which was around actually when I was at my company, the AI neuro company, which is they're thinking through doing the dual track of IPO and M &A.
Number one is, is the company ready for the rigor of being a public organization? So do they have the operational infrastructure to turn out public company financials and public company reporting every quarter? But more importantly too, on the business side, Do they have those upcoming milestones? So where are they at?
Are they like, if it's revenue generating, what does their product line look like? Are they going to have a good cadence of product initiatives? Are they going to have different milestones where they can really say, okay, every single quarter, we're going to have something come out because they really are. It's almost like you now have a flashlight shown on the company that wasn't there when you're private.
And so it's really understanding is the organization ready for that? And is the executive team ready for that as well as the board? Okay. that's what the IPO what about the M &A route?
Yeah so the M &A route makes more sense in a couple situations. One is if there is a synergistic M &A where it's like you meet you may have a partner like a merger of equals situation where you may have somebody who's a complementary product or a product that could align really well where you can fit in nicely with that organization. So that's a good opportunity. Or if you're looking to go public but then as you're looking to go public a larger organization may say, okay, you actually make sense to be in our complimentary portfolio.
Then that may make sense for you to say, okay, this is a better path for us long -term versus being standalone. Because if we think about what is the end state of our business and our product, let's go that route. Okay. M &A is another term, just like IPO, we hear mula when we hear, like, we're getting bigger.
And then finance and accounting is like, oh, we scared. Go ahead. Oh, you can feel it. No, exactly.
Well, it's funny because I've been through, I think, on both sides, the buy side and sell side. I think I've been through over 50 in my career. And I think the thing is the transition with the people, the finance and the operation. So there's like.
three different sides to M &A that people just don't even realize. Yeah. So curious to hear your stories, especially around the buy side versus the sell side. Like what are the things you probably learned the hard way and now recommend people do?
What are they on each side? Yeah. I think, um, on the thing I recommend people don't do is don't ignore the people on the transactions, especially when you're thinking about these ones, like the mergers of equals concept, where when you're combining companies, because there's value between the combined organizations. Because where I've seen that go awry is if, for example, you don't think about, okay, lockup agreements for the individuals, so you don't think about the compensation arrangements beforehand, you may lose key individuals from both teams.
Or the other piece too is if you're scaling an organization and you combine the two organizations, now all of a sudden you have double of everything potentially. So you may have two IT organizations, your finance teams, you may have one organization that's more robust or oftentimes the transactions I've been through, especially on the buy side, we had a very robust finance team and then we acquired a company that. didn't and we hadn't, and sometimes we hadn't thought through, okay, what does that look like?
So it would oftentimes take a lot of cleanup of that organization post transaction. And there wasn't consideration around how long that cleanup truly takes. So it was things like that to think about upfront. And then on the sales side, like you just said, you, you acquire a company, you have to do more cleanup.
What would you say and how should finance be involved when they're in the sales side process or the buy side process? Because I feel like we often not included. conversation and then it's like why don't you guys have your stuff together by now we should be involved as early as as possible because of the lens we have in finance we tend to see businesses at that like 10 000 foot level so we can identify early on in the diligence process if there's gap in the organization so like you can look at a finance um like you look at the balance sheet oftentimes and see, okay, are they missing key obligations?
Or is there something that we see post -close where if we look at the employee agreements, is there some employee that may or may not have a compensation agreement that should have? Or does somebody have some interesting compensation agreement that may become an issue afterwards? And so if we get involved in the diligence process, we can usually see pretty quickly some of the potential things to look out for during a transaction. I'm curious to hear any war story or horror story, I should say, during the M &A deal.
Like you were like, ooh, we're not doing this again. The one was, there was one I was dealing with where, so I was on the side where we all agreed that we were going to keep it as confidential as possible because we all knew the transaction was going to happen about six months beforehand. On the other side, and this was from most of the employees, so there's only a handful of individuals who knew, the senior executives and that was it. The other side, because it was we were combining the companies, the other side did not opt to do that.
So they told the entire organization of 40 people that they were going to get acquired. So because of that, they started changing things in advance of the pending acquisition. And so they would do things like they raise people's salaries, gave them promotions. And then they also decided part of the combination was we were planning to combine a new tech platform.
So they also decided to go change the tech platform. And so we now had a situation where we had to deal with not just combination of two tech platforms, we had a third one. So is a lesson learned? I would make sure that everyone agrees up front who's involved in the diligence process, what we're going to be communicating beforehand, during, and after.
Because those decisions made by the team on the other side led to some interesting dynamics post -close. Wow. Yeah, that sounds like the worst. Yeah.
It created some fun integration concerns. Oh, wow. Thanks for sharing. Now, looking ahead, I know there's a lot about technology changing fundraising, uh, whether it's MNA going IPO.
Do you think AI is changing the way investors discover or evaluate companies? Like how does it affect that CEO CFO relationship? Yeah. So I do think AI is changing it in a good way.
And what I mean by that is AI is allowing number one for the potential discovery of organizations that may or may not have been targets beforehand, because you can do a lot more diligence quicker. with AI. Anyone at this point can build a simple agent within their LLM of choice that says, okay, I want to discover X, Y, and Z and target these industries. So you have that all the way to you have fully robust built out diligence agents that can really help you figure out these processes.
So that is speeding up the M &A process as well as the IPO process. And then what that means for CFOs and CEOs is you can also expect deeper questions during the M &A and IPO process. And then as well as you may get a random outreach or inbound from investors that you may not have even thought of before. But on the flip side, CFOs and CEOs can use AI to think about, okay, if you want to ultimately go through a transaction or IPO process, who are those targets you want to reach out to?
So who are those investors or who are those strategic partners that you may not have originally thought? thought of that could be tangential to your typical targets. Nice. Nice.
I'm always looking for stories, right? Is there any set out story from your time as a CFO that really taught you something you want? CEOs, founders, or finance leaders to here. Because like you said, AI is changing how we do M &A, IPO, how we do finance, how we do work overall.
But one thing I'm sure is there are certain things that will not necessarily change. Like you said, for example, there is an M &A. Let's agree on what we say, what we don't say. What is probably a story that helped you kind of develop your to do and to don't list?
Yeah, one was interesting to me and it was actually about five or six years ago. So it was one of the first venture funds I've come across that was actually using AI in its process was I did diligence. I was sitting CFO in -house and we were doing a series B fundraise and a venture fund approach us and their entire process was done by AI. So they actually let the algorithm determine whether to invest in us or not.
And the way it worked was it was a two -part process. They met with us. So it was the analyst and then the algorithm recorded our pitch and then they went through our data room and that's it. And then they give you a score and then they say yes or no.
Wow. That was the most interesting thing to me but what I took away from it was they did give us compliments on our data room, ultimately decided not to invest because of the stage of the product. What I took away from it was make sure our pitch is on point and then also always make sure your data room is clean and truly tells your story of the company because you never know, okay, when somebody is going to choose to say we're going to rely on this technology that we've built that has our internal knowledge and go with it.
Wow. See, this kind of thing makes me both excited and scared at the same time, right? I'm excited because it means that I can check myself, right? If I have that algorithm, I can double check to see where are the gaps in my data room, for example, the gaps in my pitch.
So it allows me to be ready, but then... can be scary if you have been in this process for a while and now AI comes and you're like, oops, where do I start? Exactly. Yeah.
And so that's always the hard part is like, you have to think about, okay, how do I prepare? But then the AI can also conversely, it's like, okay, that AI was judging us, but then now we have access to AI that can help us prep. and think through what we're missing. So that's always a good, that's a positive of it versus, okay, the AI is telling you yes or no, it's going to invest.
Okay. And in your experience with fundraising and M &A IPO, we can see how the CFO role is becoming more and more involved and be that second person in charge next to the CEO. What are some things you will say should be included? Like people should make sure they include in their fundraising pitch.
Yeah, so in their fundraising pitch, I'd always include who the team is. And importantly, what one of the things in the pitch that typically happens is they put logos of everybody. I would go a step deeper and say, here's who everyone. like where they came from and why they are the perfect people for this team.
So really having that piece of it and then the other piece is of course what you plan to do with the funds. So sometimes that gets left off and then one item that I've also seen because you really only want five slides like usually in a teaser slide then of course you have the detailed conversations everything but really the why you should invest and then why you shouldn't invest. So like here's your overview slide so somebody can see really quickly What is it that makes you special?
But then conversely, the ones that do really well are the ones that have said, here's why you shouldn't. And here's the things that why, like why we think you might not be the right person for us. And we've thought through those. Nice.
Nice. Yeah. Definitely wanted a simple deck for the audience when you get it. Yeah.
Exactly. Cause the deck really leads to a conversation. Yes. And I like that you keep it at five slides and not like a...
Exactly. Everybody is busy and they want to see, okay, yes, I want a conversation or no, this is not right for us. And if it's not right for you, what'll happen is oftentimes investors will say, I may not be right for you, but I may know this person who is. And how, what are some of the things that helped you become a better picture if I can say a better fundraiser as a financial person because you're studying in forensic accounting, which means you were part of the people who said something is wrong, which is quite different from giving me money.
Exactly. Well, it was interesting because back then you had to say what was wrong, but you also had to go on the stand. and explain in basically, well, one of my partners I worked with used to say, we have to explain this in terms that a 10 year old can understand. So like, for example, dividends, that's always fun trying to explain to someone or at the time the mortgage industry was collapsing.
So credit default swaps, trying to explain that very simply was challenging. So what makes you a better pitcher is understanding communication. So I found some of the biggest skills that have helped me in my career are actually non -finance skills. So for example, I took a negotiation class in college that has been a great class for me because it tells me how to learn how to listen more than I speak.
And even today, I really enjoy listening to individuals. So I listen to a great podcast, Diary of a CEO. I love hearing those individuals talk about communication. Because that's really what a pitch is, is it's how do you talk to somebody and deciding on both sides of the table.
Does this make sense for a long -term, basically partnership? Nice. Nice. Yeah.
I also realized that in my career, at some point you're, you cap out of your technical skills, taking you somewhere. It's like everything is more on the human side slash softer side of skills. Now. I have two more questions for you before I leave.
First, you are a board member. You've been advising boards. And I feel like, especially in the CFO community, C -suite community, I've noticed that being on the board feels like the next natural step, right? Helping with governance and things like that.
What would you say people should also be mindful of getting on the board? Exactly. It's a great question. So the other thing to be mindful of is a board tends to be a longer term journey and relationship than your CFO journey.
Because when you're committing to a board, you're committing for whether things go right. or things go wrong because what happens is you're, you're there, but you're not in the day to day. So the phrase is always often knows in fingers out, which means like, okay, our tendency as CFOs is really again to the details, but the board level, we really need to. to help with governance.
So making sure we ask the right questions. And so when you're thinking about whether the board journey is right for you, it's really asking, and this was part of my journey is, okay, do I align with the mission of the company? And is it a place where I can truly make a difference? And so can I really say, okay, what value can I add to that particular company?
And is it a company where I really want to help them grow? And what can I bring to the table? So like we were talking about the M &A and IPO experience, the company, the board's I've chosen to join tend to have that need. And they also have that healthcare alignment because that tends to be where my passion is.
Oh, nice. Nice. Any, any scary story you want to share about being on the board or dealing with the board? Of course, all poor conversations are confidential also.
Um, I'd say one. Yeah, one of the more interesting conversations I've had at the board table is often when you're dealing with board conversations, I've gone in calls out of the blue where someone has done something that they probably shouldn't have, and then we've had to deal with the consequences. And so that's always the challenge is where we've had a management team member do something and we've had to figure out how to do that and also how to have that conversation with them about number one, why did they do what they did?
And then number two, how do we address it? So that's always the part. It's like, how do you, because when you're at the board, everyone on your board is a peer and then your management team is also there to, you're there to help guide them. So that's the conversations that we tend to have.
Oh, good. Sounds good. Then last thing, last thing I promise. What's your favorite thing to do outside of work?
My favorite thing. Oh, outside of work, it's fun doing a lot of different things. But right now my favorite thing is I spend a lot of time on my Peloton app and that means I'm running. Yes, I'm running with my dog.
So we've been doing a lot of training for races. And I recently just did the half marathon, um, down in surf city. So Huntington beach by the beach. So it was awesome.
Oh, so you race with your dog. I do. Well, she doesn't go to the races because if we did, so she's a Siberian Husky. She would totally just want to meet everybody.
But she's my training partner. So every morning she makes sure that we get out the door because if we don't. Huskies love to talk. She talks to me and tells me that I'm procrastinating.
So she's the best personal trainer ever. Oh, wow. That is so cute. Oh, thank you so much for sharing.
This was such a great conversation. I hope we get to see a little sample of your PJs because I always get questions from the audience about practical ways that they can apply some of the things that our guests are sharing. So thank you. Thank you.
Thank you so much. Yeah. Thank you. This has been awesome.
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