"A leader of an organization potentially, depending on the individual, should change and transition along the way . So the technical founder early on may not be the right founder or may not be the right leader for the organization post scaling up and growing. So having the self-awareness around that, I think, is critical."
Asking the right questions to structure thinking – Chirag Gupta
Focused career on investment banking and consulting support to growth stage and middle market companies with extensive experience across mergers and acquisitions, debt, equity and alternate capital financing transactions. Having grown up on a predominantly sheep and wheat farm in central New South Wales in Australia (Waterpoint Lane was the road leading up to the farm), in 2019, I re-established his connection with the land and sustainability of our food supply.
I see a need and an opportunity to drive change in the way we think about our food supply that secures a lasting and sustainable legacy for future generations.
I will focus on investing WPL’s equity and alternative capital through a limited partnership / co-investment structure to enterprises focused on the sustainable food system. Additional support will be provided to portfolio companies through business planning, strategy and growth advisory services.
The full #OPNAskAnAngel talk
Ben: Yeah looking forward to it Matt
Jeffery: Well Ben what I think is awesome about getting the opportunity to chat with you today is that I’m going to say that as far back as I can remember Canada has always been compared to Australia they always say it’s the same Market I’ve never actually got to ask this question and if I have it was never live so it kind of fits into the motion so we’re going to talk about that and the differences or if there is any and then outside that uh the way we like to kind of kick off our show is we want to learn a little bit about yourself if you can give us an overview all the way back from Deutsche Bank when you’re working as an analyst all the way through from uh Grant Thornton all the way up to RSM into where you are today and then one thing about you that nobody will know and then I’ll add that the other part that’s really exciting about our conversation is that from all the different areas that investors come in from you’re really hitting up on the food Tech side and I think that’s pretty exciting so I think there’s a lot of great things we’re going to talk about in the next hour so I turn it over to you Ben but chair away.
Ben: Yeah sounds fun well I’m definitely looking forward to the conversation and uh definitely looking forward to talking about the differences and and uh and otherwise between Australia and Canada show um so I get I guess to that point um yeah the accent is obviously Australian for those that are obviously uh maybe comparing it to South Africa or New Zealand but uh I I grew up in a sheep and wheat farm in Australia um and and that will become a feature of the the circularity to to the story to some degree um I uh I went to Sydney for University I was actually a materials engineer by study uh but very quickly realized that a career in engineering probably was ultimately going to be for me so I am uh managed to um uh end up at Deutsche Bank and and the the reason through that was uh I actually participated in a co-op program at uh at University and and my last work placement was with uh with the Telco in Australia um Telstra um and fortuitously to to this story they closed their materials research facility down just as I was rotating in and ended up in their business strategy team now kind of fast forward uh a little while and the the manager of that group basically sat me down and said what am I doing with my career in life and uh suggested that um I should have two paths one Investment Banking or a second on management consulting and he was a ex Management Consultant himself and you know one thing led to another and and as you pointed out I ended up at Deutsche Bank in in Sydney so you know direct from the fire hoses and Analyst at Deutsche Bank for a while there kind of learning the the financial markets you know having kind of studied it as an engineer um you know spent some time in London with that that group and then uh you know got an opportunity um to get exposed to a mid-market transaction um through Deutsche Bank which obviously not something that would they would typically work on most the transactions were working on a large you know multi-billion dollar kind of M A transactions a capital raises Etc and so that exposes to a mid-market space really gave me uh exposure to entrepreneurs and and I would say people that had a more vested interest in the transaction process then obviously you know like uh boards and management teams with large corporates did so uh that that appealed to me so I ended up um leaving Deutsche Bank and joining Grant Thornton in Australia um so I worked there for you know the better part of uh of 10 years or so uh before I met my now wife who’s a Canadian uh in Sydney uh she was there for us to comment and you know one of those that uh ended up being there for about three and a half years longer than she had originally anticipated uh but she did end up coming back to Canada and I followed her back across and uh that was in 2012 so uh just over 10 years ago now and um since that time I’d I’d worked at Collins Barrow which became RSM uh ultimately kind of leading their deal Consulting practice here again focused on m a corporate finance um but again in that mid-market space Entrepreneur Space working with you know family officers entrepreneurs High net wealth investors um and um and other mid-market clients sort of going through a transaction process um so then I guess the Confluence of events occurred you know on the on the professional side um you know I was I was leading um private Equity practice at RSM I was leading the deal Consulting practice found myself doing a lot of um internal work um less working with clients and then on the on the personal side you know obviously kind of covered rolled around it made a lot of people think about what they were doing with their life um and uh I’ve uh I guess at the time had a you know 12 month old daughter she’s now three and a half and that made me think about like the world that she was growing up into as well and so you know that’s where the Genesis for water Point Lane really started to to um you know kind of cultivate in my mind at least and then the Domino that really fell um to to creating water Point Lane was was ultimately when a family office approached me and you know they were looking at a an opportunity to invest in a in a food tech company a plant-based food opportunity and it’s just given my expertise in in the space to some degree that they’d that they’d seen I helped them through that transaction and I think facetiously at one point through the process said I’d write a check into that deal and they said well okay well if you’re going to write a check we’ll write one with you and we’ll do it together and you know we uh we put a you know a numbered Co together you know became that investor and then that that formed the Genesis for me putting a a plan to them around what I thought waterpoint Lane could be in relation to investing in in the food and AG space and they uh they were supportive of that strategy and that’s ultimately kind of where it went so I I left RSM in July of of um 2021 and launched uh waterpoint play officially in August of 20 21 and so just over a year old now and uh having a lot of fun doing it
Jeffery: Awesome and that uh that’s a a great lineup to your background and kind of where you’ve landed today and before we jump in one thing about you that nobody would know.
Ben: Uh not a lot that my wife doesn’t know but uh um in in terms of most other people I would say though when I moved across to Canada for some reason I just decided I wanted to run a marathon um and uh um certainly wasn’t a marathon runner at the time and ultimately ended up running three marathons consecutively um before I decided that was um not the right um thing to continue to do on a go forward basis as I was getting older but I do have that bug still and so um I plan to run a uh an ultra marathon uh this coming year in 23 so uh we’ll see how that pans out.
Jeffery: Oh that’s awesome well it sounds like uh it was with something that you needed to do since you did three of them and uh even though you said you retired to jump back into the one that’s even tougher than the marathon so I guess uh it was all worth it it’s pretty exciting we’ll.
Ben: See how we go
Jeffery: I love it so we’re gonna kind of like Propel backwards here into where you became an analyst but one thing that really kind of stood out to what you shared was that you had somebody that you met early on that kind of helped you decide two verticals in areas that you should go into maybe share a little bit about that because I think that’s pretty important you don’t normally hear that especially at an early stage that someone’s saying hey you know maybe you should look at this I’ve analyzed your skills and you should be kind of going in this direction I I think that’s pretty amazing.
Ben: Yeah I would say I’ve had the benefit throughout my career of having some mental slash inferential people that have helped guide me in in directions you know based on what they see and I think that’s important for for people obviously as they kind of navigate their careers um and so you know it was it was an interesting discussion because I guess I was you know working at uh at the company Telstra at the time and and he’d he he kind of called me into the office one day and sat me down and it was it was a pretty uh blank and transparent conversation around um you know where my career was headed and and you know I may remember it slightly differently than than reality but you know I what I do remember is that he he said to me you know here’s your options and if you don’t choose one within the next six months or so I’ll I’ll fire you and you’ll have to make a choice otherwise then I’m not sure how how um uh how real that that threat ultimately was but um it did maybe maybe think about the options and and you know as an ex-consultant he’d introduced me to people that he’d worked with in the past he he got the corporate development team at uh at Telstra introduced me to the to the banking options that are available to me and I think you know help me think about you know what does that path look like and and you know what is my skill set and where do I want to ultimately kind of go with my career so I think those those periods as you’re going through your career to kind of stop and and just kind of look at the bigger picture I think are important and having people that help you navigate that um Can can be hugely beneficial of course.
Jeffery: Well I think that’s huge and and very helpful for sure and and I can think back um when I was working at Loblaws uh at the time I was in the uh running all the e-commerce platforms at the time after I switched over from the engineer side and uh software aside and and it’s interesting because my boss sat me down I think it was for an annual review and he sat me down and he said um you don’t belong here and I was like what what do you mean I don’t belong here and he’s like uh the way you work and the things that you come up with and do you don’t fit here you should be in a startup and I was like what what do you mean but I didn’t know what to say I’ve I was kind of like shot and I I probably left feeling oh why am I feel so beat up but it was the first time I actually had heard that and I had been a startup way back before so it was fascinating that um it wasn’t like directional like you said where it was if you’re not out of here in six months I’m gonna fire you but it was it was interesting because it was the starting point to when it did actually um probably within a year I was gone and on my own startup so it was uh fascinating on how these little things that you hear kind of around you or somebody faces you um with that question uh that you start to kind of maybe think they’re right or I gotta dive into this deeper so um it’s kind of cool that you had that even though mine was more direct and I had to figure it out that you had the coaching and the mentoring side which probably made it a lot easier of a transition than just figuring it out but.
Ben: I think that that’s very valuable absolutely definitely helped for sure
Jeffery: So now you kind of jump into the analyst side and what I love about the fact that there’s two areas that really get the most emphasis in startup world and that is lawyers and accountants they tend to get to our Bankers because they understand financials and they tend to be the ones that really drive the most understanding of how a startup works when it comes from a corporate side everybody else doesn’t really maybe they get a little bit of it but those two areas really have this hypervision of where a startup can go and how they can help and help them structure it and move a business forward so now taking this understanding that you have being an analyst I think it makes a real big impact on how you can start shaping a startup especially in the future maybe at the time you weren’t looking at that and until you said you were working on that one project maybe there’s a couple of things that you can share that really do provide that value to someone that’s new they’re going into the work environment I find that getting a job at one of these at a bank or at a McKinsey like a consulting firm wherever it might be it’s super valuable especially if you think one day I’m going to get into a startup how valuable was that to your career being able to get in there spend those years really diving in to understand modeling Frameworks governance and maybe share a few things that you took from that experience.
Ben: Yeah I think um the the big thing that I took you know obviously as an analyst I spent probably not 95 of my time in front of an Excel spreadsheet at Deutsche Bank and um when I say 95 of my time like 95 of all my time not just you know my work time because you know work time was was all time at that point but um I would say you know just just the the the rigor around understanding the numbers um because I think you know too often that you know you can kind of get a little bit um misguided by by Mission and and um the uh you know the market opportunity as opposed to you know what are the real fundamentals that are you know kind of driving the business and you know it um especially you know we’re obviously kind of going through a macro um environment at the moment that uh you know is going to be challenging and is getting increasingly challenging uh especially for startups and and you know just simple things like understanding cash flow or cash burn and and you know where that where the um you know the you know the the revenue and margin profiles are um and compared to you know other players in the in the industry or other players in in similar sectors I think that rigor around that type of analysis um and then be able to project that forward and understanding you know what are the drivers that can be pulled from a business perspective to um hit certain scenarios and I think scenario planning and scenario analysis is something that people say a lot but don’t do incredibly well a lot of the time and so you know I’ve spoken to a ton of startups obviously over the last year or so in relation to um you know a raise that there are obviously you know looking at doing and you know it’s challenging them on on on their projections and where they think the business is going around you know certain assumptions you know you can see that the the startups that have spent a lot of time and thought uh in in that scenario planning world and those that have it because I end up with a pretty one-dimensional view of of how their business is ultimately going to unfold and I think it’s pretty naive obviously to to assume that you know the projections that you set in 21 or 20 or you know you know even now are going to play out to the to a singular uh degree and so just understanding how the business can be can be flexed to to respond to market conditions and I think are super important and I think that’s definitely the the key thing that I learned as I was kind of learned you know kind of learning the ropes at Deutsche Bank and and then you know I’d say the the second thing because you know but you know investment Banks typically operate pretty flat trucks as obviously you know you have your your levels but you know it’s it’s not super heavy so you know you end up with a lot of exposure to MDS that have you know 20 30 years of of investment banking experience they cut to the chase pretty quickly on on on opportunities like you know we’ll spend you know two weeks working through a you know a deck um to to pitcher um you know a client on a strategy they all already know what they they expect to pitch because they’re so in tune with the market and just being able to cut to the chase on on on strategy and and um using that data to support that strategy I think is is super um super interesting to to see and yeah something I’ve obviously continue to learn um to this day obviously as well.
Jeffery: Now that’s brilliant and numbers tell a great story and if you can understand the numbers you can really start to strategize around them and start to pick that apart and figure out if there’s uh there’s a gap that you can take now to to kind of jump onto that strategy side um is there a certain process that you like to use when helping a founder or business work through a strategy like do you have certain terms because I’m going to say that 95 percent of all founders probably don’t really understand strategy and especially when it comes to financials there’s probably even a bigger gap on really understanding really the metrics and you spend a lot of time in a spreadsheet and then you
switch over and now you’re on PowerPoint uh um winning the world through PowerPoint and you know you kind of have to bounce between the two so how do you coach that and what does that look like for a founder.
Ben: Yeah you know I think just you know coming it does you know in in my mind um and you know I I look at the lens through my um the lens of opportunity through through my experience it does it does come back to you know what what do the numbers actually tell you and and I I would say you know you’ve probably seen the same um you know we see an investor deck that you know talks to a total addressable Market of you know x billion dollars it’s always some some billion dollars market like it’s three to see one that’s less than that um and and yeah therefore you know we’ll take one percent of the market and therefore you know we’re you know a hundred million dollar plus organization now it’s all great like you know percentages on a spreadsheet are taking one percent of the market uh is is interesting but it’s certainly not um you know how how business works and so what what I like to do when I see these types of opportunities and and certainly when I’m talking to that to Founders is kind of say okay that that’s great to have goal posts but like I want to understand what the three or five year execution plan ultimately looks like to get there so let’s break it down from today as to where you’re at is what is what is the execution strategies like what is the channel strategy yeah what is the sales strategy what is the marketing strategy what is the operational kind of strategy to help execute and build up on that because if you can’t demonstrate that in a in a progressive fashion then I can’t believe in your addressable Market opportunity um and I think that’s the area where and again you’re kind of bouncing that around with scenario analysis and and you know what is the what is the the flex in the business if if this goes wrong or if this this goes right and if this actually goes better then then that you know does does um how does the business adjust to those types of principles and I think that’s the area where I spend a lot more time on my analysis on on opportunities and certainly as I’m talking to um you know the companies I’m working with.
Jeffery: So does that now put when you’re diving in and educating the founders in these processes and building them up or maybe they’re already advanced enough does that put you kind of trying to look at more of a seed plus series a type company because the knowledge is not going to really be there or the understanding maybe so you are looking for more advanced based companies maybe today or even back then.
Ben: Yeah like the the Investments that we’re making today in water point line where you know typically in that series IE through C type um round and I say typically like my investors my LP investors um we’re not taking Science and Technology risk we’re taking scale up and growth risk um and we like to see businesses have proven out that there is a there is a market opportunity and a market for their product or service um and it’s it’s proven that there is a market opportunity and they just need fuel to the fire to help execute on that growth and so you know I I obviously you know bring a bring a financial lens to help support the companies as they’re going through that process and I’ve got a group of operating partners that have other expertise you know Ops production agri-food sustainability cpg World data science science and AI to help you know support the companies in areas that I don’t have the right skill set and that’s certainly a feature of obviously how we like to invest is is to be supportive of our of our companies in in their growth plan.
Jeffery: I love it and when you’re going back to um your Grant Thornton and and more the corporate finance side are there things that you learned along the way that you never thought were to be applicable to early stage and today they’re more applicable than ever is there something that kind of stands out that you were like I can’t believe that this was never implemented everywhere.
Ben: I think that the the key thing I learned through that entire process um and I would say you know it’s a it’s not something that uh I don’t continue to learn on is is just the almost the psychology of of of entrepreneurs and and uh business owners and I think you know when you when you’re at an organization like a Deutsche Bank you know you’re dealing with yeah to some degree a bit of a removed set of individuals from the ultimate outcome. Yeah sure they might have a little bit of equity obviously um in the business but but more often than not you know that you know that’s large public companies um you know the the Shepherds is obviously much more diverse the companies that we’re typically dealing with Founders are you know 50 60 of the the share rate just uh um you know previously when I was with Collins Barrow and Grant Thornton uh RSM days you know dealing with owner operators that you know and 100 of the business and and you know this is likely to be there in the transaction you know they’re not serious real transaction people and so a meaningful outcome to them is Meaningful not just from their perspective with the business it’s a very kind of personal and life-changing Experience One Way or Another and and potentially intergenerationally and so helping them navigate that process you know the highs and lows of a transaction process because you know it’s not always Rosy you know there’s uh there’s issues that come up you have to navigate those issues whether it’s valuation whether it’s steel structure and process and so just working through those issues with with um entrepreneurs and so it helps me kind of think about the the mindset of entrepreneurs as as I’m working with with um with startups now and and I I probably ask questions through the process that I would say some entrepreneurs are a little confused about because I’m trying to understand yes to some degree some of their psychology not just not just their their ability to execute on a business plan how they may ultimately respond to uh you know issues that come up you know whether it’s transactionally or whether it’s operation in their business and and get a better feel for them as an individual as opposed as much as I feel as a leader of their organization.
Jeffery: And you find that there’s a there’s a difference between um a technical founder or a numbers founder than it is between someone that’s more operationally mindset or someone that’s more on the marketing side are you finding like there’s a significant level of understanding or how they work with you at the same time.
Ben: Yeah like I would say there’s there’s multiple types of Founders and leaders obviously in and understanding which type obviously you were working with and dealing with at the outset is is critical to how I would obviously deal with them but it’s also critical understanding their team as a result of that and so you know no one’s perfect no one can have all the skill set obviously you know I don’t purport to have all the skill set required and that’s the reason I kind of have a group of operating partners that I work with and so that’s kind of how I expect a a management team to kind of build themselves up you know technical competence operations and growth uh Marketing sales Etc and so depending on the the leader um and how they’ve kind of put their team together I think the the other point is is a leader of an organization potentially um you know depending on the individual should should you know kind of change and transition along the way so you know the technical founder early may not be the right founder or may not be the Right leader for the organization kind of post scaling up and growing and so having the self-awareness around that I think is critical as well and so I certainly talked to Founders I’m dealing with around how they see their
transition in the organization over time and if they’re self-aware enough to understand that they’re not necessarily going to be CEO forever and understand how they may respond to that either positive or negatively accordingly.
Jeffery: And we’ve been talking about this a lot lately over the last couple months and getting different perspectives because it is going to change especially as a company grows and only because we uh earlier chatted with the Elon Musk effect or things like that but you know even when he came in he was the marketing side and and maybe he’s the vocal brain side who knows it could be a mix of everything um but you know the company like Tesla was originally started with engineers and they built the company and Elon came in and layered on top to take over that so is that um you know they had to accept that they had to say you know what we want to be big and huge or do we want to just keep operating the the way we are you know how do you like even from your past experience did you find it as you’re deep diving into these companies and doing this analysis that you’re actually seeing that maybe through the numbers or through the interactions that you know maybe this founder isn’t there and you’re like I want to say something but I’ll hold my tongue on this one and let the senior level people throw this out there at them eventually if they even see it is it something that you can pinpoint and if it is something you can pinpoint what is the lesson like what do you look for and and so that Founders can say yeah you know what maybe I’m thinking that even though we’re at a series a I’m already feeling that I’m not the right fit and I got to get someone that comes in here that can be I
don’t know more of a cheerleader or more of a marketing person you know what does that what defines that.
Ben: Yeah and and I would say like I very much like to have very transparent conversations with um companies that I’m working with and companies that I potentially would work with very early on um I you know obviously Australian I mean coming out to some degree but I would say you know I don’t like to be um you know kind of finagling around the issue I would just like to get it get it up front and on the table and and discuss it and and see how um your perspective aligns and I’m not saying I’m right all the time obviously for sure but you know I I certainly like to understand how a Founder may think about their transition um I’ve certainly passed on deals where I thought you know the founder just isn’t the right guy you know I do know that I’ve um that they’re not going to transition accordingly um and I just see that as too big a risk to get over um but I I do um like to to talk about it in the context of the scenario planning and scenario analysis that we’re doing through our diligence as we’re looking at um you know the options that the business takes on a growth path and so you know when when you know I’m looking to business and you know they you know they put a nice projection in front of me which is scaling it you know plus 50 year on year and at some point you can see like the business based on their projections just looks fundamentally different than what it looks like today you know the the op structure is you know five times the size you know it’s it’s maybe it’s more of a sales and marketing organization that is a technology and r d organization so that’s where I like to start challenging that that perspective on on how the the founder sees their role and so you know when when you see the you know the the P L especially on the on the um uh Opex side you know kind of transition from that uh that Heavy R D and product development side to you know sales growth that’s where I like to say all right well now this this organization is no longer a development organization this is a growth in sales based organization have you see your role in you know where do you see yourself fitting in and just again being transparent around what that would look like and could look like at any rate.
Jeffery: It does come back again no matter what it comes back to the numbers when you start to look at and you know I learned this through my my days at Loblaws when back in the day too is that when you started to look at who is coming in as the CEO and now that’s obviously been revamped a few times but when you looked at when we were in a recession or downsiding it became the um the CFO that was rolling into that position because they were in to be cost cutting measures make changes stabilize the business and then when things are ramping up and going like crazy then you brought in a product person and that product person went up and taking running the company and it seemed to bounce between product and um Finance versus marketing and other vehicles because really at the end of the day I think there’s there’s really a strategic side to understanding your product but there’s also a strategic side to understanding how to expand and or Shrink based off of the financial numbers and you know you can even take it even bigger to companies that we see from like uh Howard Schultz at Starbucks bucks were you know built a great company stepped down probably I think I’m going to make the guess three times in 2000 maybe 2012 went back in stepped down again and then went back again in 2022 so you know as much as you think you can always stay away but there’s also the learning you take from that to where that founder comes back in um and uh as a one to two percent um owner of of shares and uh um Starbucks he still has the control to be able to do that I’m going to assume but I think people believe in what they’ve built and what he’s built so I don’t think it’s something that a Founder has to be worried about I know there’s always the fear that um the board’s gonna kick me out or I’ll never be able to come back in or they don’t like me or what’s going on but I think to your point there’s that uh suggested um play that says you know are you the right person at this time it doesn’t mean you have to exit the organization it’s what is the best for the organization in order to continue scaling or growing.
Ben: Exactly exactly and and you know it can be hard for a Founder to disassociate themselves from their their baby to some degree um you know as they’ve you know kind of built and led the organization to a point but you know you also kind of talk about in black and white terms you know they are as as vested as anybody in getting the right economic result for the business going forward so you know we’re a minority Equity investor we’re typically um you know holding less Equity than a a Founder um often you know when we’re actually writing a check and so you know there is they’re more invested than we are ultimately in their in their outcome and so you know if we can’t sit down and agree that the right outcome for a business may be a transition of their their their role within the organization again as you say not not to step away from the organization but to take a different role in the organization based on you know where the company’s at at this particular time and where the market is at then uh and that’s an important decision point.
Jeffery: And you mentioned the psychology of it and again because you’re coming in at a series a versus uh early on at this pre-seed and Seed there’s that build up phase the run-up phase the crazy stuff happening the ups and downs um until you get to more of a scale and stable side how does the psychology work within these Founders especially when they get to that series a side um we see it we’ve had companies go public we’ve gone through that stream but um a lot of the times the founders will step down and we had that happen when the company one company was going public the founders stepped down to bring in somebody more senior more public facing and then had to jump back into the business because they didn’t understand the hustle of what it takes to be in that type of business because yeah you can streamline it and turn it into a process and commercialize but if you’re not getting the the drive and the hustle from that real growth phase type of founder then you accomplish one thing which was get it public and have the public face to it but you don’t have that same hustle behind it so what does that psychology look like when you’re talking to Founders and I love this I think this is very influential and understanding because a lot of Founders out there are scared they’re like I’m and I talk to this all the time I don’t want to have a board because you’re going to try and dominate my company well I don’t want to have this because they’re going to do these things and you know there’s these negative things that are put out there but I think they just don’t realize that it’s not meant to um take over or beat the company up it’s literally there to help them get to a very scalable opportunity to grow and utilize all the brain power in that room and not just emphasis it on one right.
Ben: And and you know boards are the same as mashed potatoes right they should evolve as a company of all at the same time so you know I think you know I challenge Founders on on the governance structure um you know based on on where they’re at as well like you know you see you see boards filled with you know the the lawyer accountant um you know maybe their wealth advisor or someone kind of random like that that and then you know maybe an industry person and yeah that there’s as as they’re kind of looking to do a raise maybe there’s a spot or two for for an investor that’s coming on the race you know I like to understand like how they view the board as a as a as a tool for their their growth um and I think you know you see various boards set up you know some uh you know almost feel like they’re just there for for checking the Box um which kind of reflects that type of structure that I mentioned before others others you see are very thoughtfully set up you know that they’ve got people on their board that they they are leveraging and can you know you can see
you can add significant uh growth to the business and and so you know we spend a lot of time talking to to management around their board obviously and we talked to the board members obviously around around the opportunities and and certainly we like to play an active role from a Governor’s perspective you know where where it makes sense obviously given you know where where we’re coming in on the cap structure um but but kind of thinking thinking through that as as to how the the entrepreneurs again see see their ability to leverage the tools that they have around them is is the the psychology that we kind of look to to understand and and certainly you know to your point on on potentially exit strategies understanding where they think the business is going to go and how they expect to either monetize or uh um kind of achieve a liquidity event obviously for them and their shareholders you know do they do they want to be in this for the next 30 or 40 years are they are they that type of Builder or are they you know do they want to build and run um and then you know find something new to do Etc and understanding that that type of mindset I think is is critical um it’s it’s actually I find it more rare these days to find a Founder that actually wants to be a public company CEO um I actually find it quite rare in in most of the business that we talk to that as soon as you kind of bring up that exit strategy they’re like hell no like not something I’d like to be a part of and you know if a public company exit strategy is right or bringing someone else to be the public kind of CEO you know and maybe that they’ll want to continue a role in the organization but certainly would not want to be the public facing of it um so I think it has become a little bit more of a specialized skill set um and uh and I think it’s to some degree um it does feel a little um more challenging for for a Founder to to to get to that level because of the additional requirements around obviously kind of being a public-facing kind of management team obviously there’s a lot more disclosure and and regulatory requirements that come with obviously a public company that they they would need to get their head around but also um I I also do like to coach some of our companies that as they continue to raise capital and get more and more sophisticated investors they are going to have to start to act a little bit more like a public company in their processes and their reporting requirements and their their uh their governance structures that the transition is not as significant as they may feel um too and so I think there’s just those um you know types of dynamics that that Founders need to understand and so it kind of comes back to understanding their role in the organization as the company continues to scale because it’s not always just the public the private to public transition it’s it’s where you get certain significant shareholders that start to hit the hit the shares you know their role may need to change alongside that accordingly as well.
Jeffery: I love it and I think with all of this kind of shares is that as a Founder is growing their company they always have to be planning ahead being strategic knowing that they’re going to have to go to this commercialization standpoint and that people that understand numbers people understand scaling and growth doesn’t matter if they come in as an investor they come in and as a board or they come in as a supporting coach or feature that everything is going to be directed to help that company get to that next level that next stage and there’s different people at different levels and each one of them is a level up and you have to keep leveling up and if you’re not going to level up and I’m sure we’ve all played video games some of us more than others I love video games you’re always leveling up you’re trying to get better well you can’t get better if you don’t uh um have some wins and you don’t start taking down things so that you can get a better hammer and a better all of these pieces that make your business better stronger and that comes with the people and I think one of the things that would jump on to in that really makes a lot of sense too is that you’re able to be direct and share this background and share this information I think those are key things for anybody that’s in a business but the big one that released stood out is that you mentioned that when you go into something the board is going to change the team is going to change all of these things keep getting upgraded so the people that were on your board in that precede or your seed they shouldn’t be there by the time you get to a series A or B because that’s a whole different layer of money different layer of governance and you need to have those people that come in at those stages and have that in mind so you’re always upgrading and making those changes.
Ben: Yeah exactly
Jeffery: Brilliant well I think uh I think that was brilliant just well shared I think there’s a lot of stuff there that people just fight with they really have this bad notion I don’t know who’s spreading these rumors but um you know I I think just even from the example of um of Schultz on how he had to step down and up in order to build a company and I think that that’s highly important for a Founder to not feel afraid that from a psychological point of view that they’re going to take a beating that it’s actually really good for them in their business to be able to step in step out and be able to have that different view but knowing that they’ve got a lot of good people around trying to increase the value and drive that business in the right direction.
Ben: Exactly yeah and I think that you know we live we live in a world today of um you just generally um yeah there’s a lot of coaches in the world um Sports coaches life coaches whatever um yeah there are a lot of executive coaches too and I think um I see a lot of value in in Founders is that as they’re evolving through their business working with uh coaches as well to support their growth um because as much as they they might not have the skill set today to be the the right individual leading the company at a certain stage doesn’t doesn’t mean they can’t build and learn that that skill set over time and so you know working with coaches and having you know management teams work with with coaches to help support their their their personal development as that as they’re continuing to scale their organization can be hugely beneficial you know fit for them but as importantly for us as investors and you know other stakeholders to the business as well.
Jeffery: Brilliant I love it noted everybody when you get your things together start finding the right people that you can start coaching you and uh helping you execute and build bigger faster better companies and that that starts with the right people so well share yeah so we’re going to transition now into one of those heartfelt moments case studies um a founder or Founders that you talk with work with or even just came across um Sherry could you share an example of what it takes to be a Founder um the the Dynamics the excitement of it I think it’s an audience we love a great story uh of course we we love the story of someone just making it happen and he or she just crushes it but is there something you can share on what it does take to be a founder and what they might go through in any type of business they’re in.
Ben: Yeah look I I yeah I think founders of the hearts are Builders right like at the end of the day like you know they they want to build something and and have it grow and flourish um and so if you’re not a builder um you know I I struggle to to see at the end of the day how you can be a great founder um uh and and so you know we we look at Builders and we we talk to people that are obviously kind of building great companies um you know obviously um with a view to building a great company um early on and and you know assess you know how how they have kind of got to their point um and and yeah I would say that the one you know constant in all of the stories is there is no constant it it you know there’s no linear path to kind of building a company and scaling a company um you know we we we’re talking to Great companies now and and looking at great opportunities for companies that have taken 15 years to get to the point where they are at today um versus other companies that have taken like six months to get to where they’re at and and that there’s various reasons for all of that and and they’re all very situation specific and situation dependent you know some some Founders Builders are just a little bit too early in in the the market opportunity and sometimes the market has to catch up with them um before they’re you know they get product fit um and Market fit kind of right um sometimes you know people are just responding to what the market is doing and can scale very quickly based on on you know opportunity and demand um so I’d say the the requirement of a Founder to to be able to flex um and and flex their their path um and and not be so stubborn that they can’t adjust their path I think is is the you know almost the most critical point um as as as the markets change and you know the market today is very different from what was you know 12 months ago uh and and the ability of a Founder to to navigate that and respond to to those market conditions um you know you you’ve seen the stories of the large VC funds obviously telling their their Founders to you know kind of batten down the hatches and stop spending and and you know preserve cash compared to you know the messages that they’re getting 12 months ago which is kind of growth scale and and do everything you can to to um you know grow the top line and so you know that takes you know potentially different skill set it takes a different mindset for sure and so just being able to adjust to that on a on a on what can be a very quick basis I think is is the key.
Jeffery: It almost sounds like um what my favorite is is there’s a point in time where you just have to blow up and just keep doing it because you know sometimes your your coasting or you’re doing things in the right fashion you’re making money things are turning out nicely but things don’t feel right or things aren’t aggressed progressively moving in a the same fast upward trajectory that you’re looking for and sometimes you have to shake the tree to kind of get things moving again and bring a pulse back to the business and it kind of sounds like that’s kind of what you’re looking at and you’re saying you know maybe the market conditions are what’s uh creating the the change but you need to jump into it full Hands-On and make the the change with it so it kind of is part and parcel to the environment learn watch and and make sure that you’re adjusting quickly quick and fast but you’re also utilizing the knowledge that’s coming in on you so that you can catch it before it hits you like a ton of bricks.
Ben: That’s right and and you know we’re uh we’re a thematic investor right like we’re investing in in the system like the increasing sustainability of our Foods system and I think you know be hard-pressed to find anyone that doesn’t agree that that is a theme that is going to experience some some you know long-term fundamental change and you know my View kind of change Always creates opportunity but it doesn’t mean everything’s kind of Rosy on a day-to-day basis you know the the market as I said today is very different than it was 12 12 months ago so you know how a company navigates the next you know one two three years of of kind of turbulent market conditions compared to just you know the growth Market that existed for 10 plus years before I think is is fundamental to to you know uh you know help how we assess Founders and how Founders need to assess the the opportunity in front of them so while kind of macro thematic conditions may be favorable it doesn’t mean you know short-term um uh kind of trans uh necessarily always in the in the same direction so being able to to flex and respond and have the business respond to what’s you know near and dear let alone um you know the longer term opportunity I think is is hugely important.
Jeffery: Keeping a hand on the pulse and as you just said Flex being able to flex I like that love it that’s awesome well we’re going to transition now into our rapid fire questions the way it works is I’m going to give you an option one or two one or the other and you’re coming in from the investor side so uh choose which one works best for you and we’ll uh we’ll do the business side first and then we’ll jump in personally.
Ben: Sounds good
Jeffery: I love it all right here we go founder or co-founder
Jeffery: A unicorn or four-year 10x exit
Ben: Fully a 10x exit
Jeffery: Tech cpg
Jeffery: Nft or web 3.0
Ben: Web 3.0
Jeffery: Ai or blockchain
Jeffery: First time founder or second third time founder
Ben: Second third time founder
Jeffery: First money in or series a
Ben: Series A
Jeffery: Angel or VC
Jeffery: Board Seat or Observer
Jeffery: Safe or convertible note
Ben: This convertible noet
Jeffery: Lead or follow
Jeffery: Equity or interest payments
Jeffery: Favorite part of investing
Ben: Favorite part just making entrepreneurs
Jeffery: Love it number of companies invested per year
Ben: Uh four to six
Jeffery: Perfect any preferred terms
Ben: Uh preferred chess
Jeffery: Love it verticals of focus
Ben: Uh sustainability of food
Jeffery: Two qualities of startup needs in order to stand out to you
Ben: Mission oriented uh and and path to profitability
Jeffery: I like that uh personal side book or movie
Jeffery: Superman or Batman
Jeffery: Restaurant or picnic
Ben: Uh restaurant
Jeffery: Five minutes of Bezos or Oprah
Jeffery: Mountain or Beach
Jeffery: Biker run
Jeffery: Big Mac or chicken McNuggets
Ben: Chicken McNuggets
Jeffery: Trophy or money
Jeffery: Beer or wine
Jeffery: Yeah camera or mobile phone
Jeffery: King or Rich
Jeffery: Concert amusement park
Jeffery: Fortune cookie or birthday cake
Ben: Fortune cookie
Jeffery: Ted talk or book reading
Ben: Ted Talk
Jeffery: Tick Tock or Instagram
Ben: Neither the Instagram if I have to have one
Jeffery: Facebook or LinkedIn
Jeffery: The most famous person that pops in your mind
Ben: Oh because you said Bezos so I can’t get him out of my mind now
Jeffery: I had the same thing I’m like I gotta change the sequence so that people won’t think of the ones that are in there but it doesn’t always happen but Apple does come up a lot uh favorite movie and what character would you play in the movie
Ben: Uh Shawshank Redemption and uh I’d pay uh mind blank and his name the the manga
Jeffery: Oh the the one that the oh my God the one the one thing that
Ben: obviously escapes at the end at Tim Robbins plays um
Jeffery: Yes okay okay you know what I’m gonna bring this up again this is crazy this this factual information that it has to come out is that and I’m gonna go through and sort this out but I’m going to say that at least 50 of all investors that I have interviewed have picked Shawshank Redemption as their favorite movie
Ben: That’s crazy
Jeffery: There has to be something behind this because like is it this uh uh coming from behind and getting out and being free I don’t know but it it’s really amazing that everybody chooses that movie like it doesn’t come mine’s like Matrix and crazy stuff like that and everybody always picks Shawshank I’m like I gotta watch this game maybe I haven’t had a heartfelt moment enough and I need that because it blows my mind I just think it’s amazing so it’s.
Ben: Such a good movie it’s got so many good themes running through it
Jeffery: Agreed agreed uh favorite book
Ben: uh Shanta Ram
Jeffery: oh I don’t think I’ve heard of that one Shanta Ram uh
Ben: Amazon is actually just uh I think it’s Amazon or apple apple I think actually just made a a TV series out of it so if you don’t like to read you can get to the to the TV series.
Jeffery: Which what is it about shantaram I I love reading.
Ben: The guy that escapes prison uh and flees to India and then his his life kind of on the run in in India and his experiences through uh through India it’s pretty uh pretty cool story um it’s a it’s a thick one though I’ve been trying to get my wife to read it for about 15 years.
Jeffery: Oh yeah nice that one sounds cool I’m gonna find that see if I can uh read it up uh all right uh first brand that pops into your mind
Jeffery: Nice favorite sports team
Ben: Uh well originally like I I was a Australian sports team and I I do have a long-running affiliation still with my Australian sports teams but from a from a Global Perspective it’s Liverpool FC um and then locally uh obviously a Leafs Raptors Jays and uh Buffalo Bills fan.
Jeffery: All right I can I can go with the uh with the Blue Jays I’m not sure and the Raptors are good the the Maple Leaves I’m I might have to hang up on you but um and then uh the uh Liverpool man they’ve taken a beating this year but uh yeah they still have one of the best players in the world so I I think uh they’ve got room to grow but Arsenal’s crushing it so finally I used to have a question that was um uh what’s your favorite team between Arsenal and Manchester or something or man you and everybody picked man you and I was like okay I can’t find an Arsenal fan anywhere and now I can say oh I bet you there’s some new Arsenal fans now.
Ben: Yeah well and I’ll definitely pick Arsenal level of opinion United for sure
Jeffery: Exactly so I would have gotten there almost at the end what is the meaning of success to you
Ben: Uh being happy
Jeffery: It’s a that’s a really good success story I agree happy does make things just that much better last question what is your superpower.
Ben: Uh I think I’m calmness like I uh I would say I’m just inherently uh pretty calm about life and so you know we’ll figure it all out eventually.
Jeffery: I like it it does sound like you carry a lot of the calmness but I think coming from it from a numbers perspective I think there’s that analytical side too which is uh super helpful for uh for any founder to be able to uh uh to have and I’m sure the Surf Side and uh bringing all that uh uh differentiating stuff
that happens in uh your hometown to where you are today which we did that we should ask one more question which is is there any difference from Australia and Canada um or as everybody says it’s identical and you can say that um we should open up the borders and allow for Canadians to be able to move back and forth between Australia and Canada because they’re so similar.
Ben: Well I think they like if you hang out at beer for we still long enough you kind of feel like you’re in Australia anyway but um oh I I think culturally very similar um economically kind of feels generally pretty simple I think that the only thing I had to just get a little bit more used to is the fact that um Australia is just so remote from anywhere that uh you know it’s always very difficult to get uh get um you know kind of trade effectively done but obviously Canada has a big uh border uh just south of us that uh we have a very big trading partner with that uh yeah you just need to to understand the Dynamics with the US um a lot more than obviously had to previously so um apart from that um it’s a very smooth transition both both directions
Jeffery: I love it well I haven’t been to Australia yet maybe in my travels uh one of these days I’ll make my way over there and I’ll have to reach out for uh some connections there but I’m excited to do to go there one day for sure but um outside that I I want to say that Ben it has been a pleasure getting to chat with you I’ve taken a million notes as I like to do and lots of great things there and I appreciate all your time and diving into everything and anything great about your background and of course what you’re doing today I think it’s brilliant and again super appreciative of everything you shared and the way we kind of like to leave things off is that we like to give the floor to you the last word anything you want to share to investors Founders um I turn it over and of course please share how they can get a hold of you as well and thank you very much again.
Ben: Uh pleasure well uh the the last thing I would probably just want to leave um people with is uh we’re uh we’re doing this discussion with the backdrop of of cop27 currently going on uh in Egypt um you know a very important time for for us from a from a climate change and climate solution perspective um obviously we’re a thematic investor in in focused on sustainability of our food and AG system and we think there’s a ton of opportunity in that space but they certainly encourage Founders and investors to think about sustainability as a key portion of how they’re taking their business and the investment thesis going forward I think it’s super important you know for us as a as a as a human race at this point in time we’re out at a bit of a Tipping Point and you know the technology and solutions that are being developed um are super um interesting but also super impactful and you know the the investment Finance Community um you know the uh the regulatory uh bodies you know the provincial and federal uh funding programs need to get behind the theme at the same time to to make it all work.
Jeffery: I love it well shared Ben thank you very much again for your time.
Ben: Pleasure good to chat Jeffrey
Jeffery: Likewise that was a great conversation with Ben what I really thought was very uh impactful in this conversation was the talk about uh what people tend to think when they’re an investor or they are coming in as a board or they’re jumping into a company when they start to analyze things and say wait a second maybe this founder isn’t the right fit and and how do I bring that up or what does this look like if um this founder made that pivot or changed or stepped out and is there a psychological issue with it and we probably could have dumped jumped in a little bit more to understand is does the company have a psychological issue with this meaning that everybody who’s been reporting into the CEO and now that person’s stepping aside and allowing someone else to come in and run the business but I think overall what really stood out was that you’re not losing the company what you’re doing is you’re prepping the company for scaling and success and not every founder can do every stream along the way so I think that’s something that we all have to be cognizant of is that we have a place maybe where Builders and we’re not the scaling or maybe we’re good at doing the financial analysis or doing the uh the sales and product side I think we do have to figure out where we fit because that makes a big difference when you’re going out and raising larger funds especially at that series a side of things um and some of the other things that really stood out was um you know really pivoting and navigating to the conditions that the business currently is in and I think that’s also something that you really have to be really enthralled in and on a on a dime be able to move and maneuver the way you need and of course talking about strategy scenarios around the the the analysis side of you know your execution plan for different Channel sales Ops marketing all of these things are going to be important especially at that series a when you’re bringing in large sums of money so really well thought out and great share um again Ben appreciate that it was great to have you thank you everyone else for joining us today if you enjoyed this conversation please feel free to share with your friends or subscribe to our YouTube channel follow us us on Spotify podcast and or Stitcher feel free to share an audio or video clip around our show and we may include in one of our future podcasts find us at marketing openpeoplenetwork.com and we thank you for your support and comments they’re truly appreciated you can also check us out at supportersfun.com or for startup events visit openpeoplenetwork.com thank you and have a fantastic day.
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