CEO at The Field Group I Hudson Valley, NY Regional Angel Investor
Jeffrey Werner | CEO at The Field Group I Hudson Valley, NY Regional Angel Investor

"If it's not sustainable to you and your household -- it's not sustainable."

- Jeffrey Werner

Jeffrey Werner on worst business relationship to best.

Talk Takeaways

“Don’t lose perspective. This is an adventure. This is how you know entrepreneurship. Doing a startup, it’s how we explore life.”

CEO Jeffrey Werner of New York’s Hudson Valley shared his unique journey from a rock and roll bass player to over 30 years of audiovisual technology and eventually to his first investment in a startup. Since then he has dedicated half of his life to helping startups.

Casual mentoring, he explained, is key to helping the entrepreneurs overcome the challenges they are facing and become aligned with their vision when they fail. Additionally, he spoke about sustaining a creative ability as a motivation for founders to always move forward.



I work with early-stage businesses as a senior advisor, mentor and consultant, assisting with capital acquisition, expansion strategies and resource allocation. What fundamentally sets me apart as an advisor is my broad-spectrum, hands-on approach to identifying and creatively solving problems. I strongly believe in the value of building relationships with Founders and other personnel, which allows for a more measured and holistic understanding of someone’s business and vision. I believe this personal touch is imperative to achieving a more satisfying and successful partnership.

The full #OPNAskAnAngel talk

JP:Okay, welcome to the supporters fund, ask an angel. I’m your host Jeffery Potvin. and today we want to welcome one of our favorite investors, we’ll say of 2021 because we’ve been working on a lot of great things. I welcome Jeff Werner to the show and thank you very much for coming today.
JW: Yes, thanks for having me, Jeffery.
JP:awesome. as long as we all get mixed up who’s who. well i’ll go buy JP and you can go buy Jeffrey. how’s that?
JW: alright. That sounds good. I love it.
JP:uh, well Jeffrey, the way we like to kind of start things off is we like to dive right in. We want to learn a little bit more about yourself, your background, all the great things that you’ve done to date. and then if you can share one thing about yourself that nobody would know. Okay, so start with one thing.
JW: I like it. let’s do it. Okay, so here’s the one thing that no one would know. I am an observer of human behavior. So when you think I’m not paying attention, I probably am.
JP:Oh my god. I love that. I always use the same line actually but I find that when you’re the silent type, you like to look, watch and observe everything and you take it all in. you’re like a big database of watching what someone’s wearing, why they’re doing this, why are they doing that. so i love that. That’s a great skill.
JW: But what’s funny about that is that, although I can very comfortably be the silent type, I can also comfortably be up front. So I’ll shape shift as needed. It’s all authentically me. Um, it’s just which is the right tool for the moment. I like that. It’s an adaptation, right? It’s like being a chameleon. you’re adapting to your environment. Flexibility, yep.
JP:ah, that’s awesome. great skill. Alright, so now if you can kind of give us a little bit more of the background side, even to where you’re calling in today from. because i know being in the US, there’s multiple areas that you can be residing and working. There’s a lot of that happening of course around the world. but maybe share a little bit about that and then put into context what you’re doing, have done and what you’re doing on the Hudson Valley side and all of the other great things that you’re working in the startup space.
JW: sure. well as you just touched on the Hudson Valley section of New York, for those of you who are New York geographically challenged, it’s an area north of New York City. We considered about eight counties, four counties north each side of the Hudson River. I love this area. i like to say my playground is battery park, which is the tip of New York City right up to Hudson, New York. and I’ll let you google that. so where i am is somewhat halfway, maybe a little less in Beacon, New York. Uh, this is my office space. I found Beacon as another thing that some don’t. I’m a part-time rock and roller. I play bass guitar, something that, when I had my own business, I had to put down for a little over 20 years. and found my way to Beacon from the rock and roll scene. So I started playing again a few years ago. and I have rehearsal tonight, so that brings me up here. So when I first discovered Beacon, I fell in love with the place. and then decided I wanted to work here. So I got some office space and here i am. and How did I get here? well that even is intertwined with my rock and roll history. so i come from the event industry originally. I did 30 years doing audio visual technology, started with stage lighting then it went to sound and video. I did a lot of live events and then in later years, I installed these systems in commercial spaces. It sounds strange to go from there to angel investing but along the way, I fell away from the tech. I started running my business as it was growing. I had my hands in everything from bookkeeping, selling to running teams and turns out, it was a great experience in versatility. one saying is master of all trades. I mean what are you called, not master of all trades? yeah i’m blanking on that same jack of all trades, master of none or what i say in angel world, proudly generalist. and i find for early stage startups, we need to wear all the various hats and pull out all the various tools and juggle what you need to juggle. So I did that for 30 years. Twenty two of those years, I had my own company in one form or another. After seven years, I was approached for a merger and became a part owner of a larger company. That company was out of business a year and a half later and it was an incredible lesson in growing too fast. We were actually quite successful right after the merger . We had incredible synergies and we just grew too fast and uh we had employees. we added debt and we just couldn’t keep up with it, so that ended. about a year and a half later from the ashes of that, i started my third company that i grew into profitability and sold in 2015. I stayed on with that for a year as a consultant, part-time hopping in and out and then went on my way but intertwined into that last year or two. It was a story on how I got into angel investing. so um jumping back to my rock and roll days, i used to play in among the bands. I used to play with a guy in high school and we’d go down to the village in New York City and play these dives at one o’clock in the morning on a Tuesday. incredible experience but not very fruitful in terms of rock and roll success. so we parted ways eventually as we all got older. We settled down and got jobs and so forth. We lost touch but got back in touch. We first found each other on Facebook and then one day i’m in a shopping center and there he was with his young child going for a haircut. Now you got to keep in mind, this guy definitely fits in the village of New York City. His name is very legit now. so he reconnected, got together. My wife and I had the family over for lunch one day and he showed me a deck on his tablet. and i recognized some incredible genius that i saw in his songwriting some decades back. I didn’t understand it but I recognized it correctly when I said human behavior. I recognize a creative genius there. So we kept the dialogue going for a number of months and after I’d say about eight or nine months, he and a partner decided to leave their day jobs to build this company. and I said great. What can I do to help? so i set him up with an office and wrote my first check. and in that time, you know just started getting this thing rolling, and in that time, they wound up pitching the Hudson Valley Startup Fund. So I’ll jump to an end quickly. I’m now one of the managing members. but at the time, i had no idea of any of this stuff. but they came back and said Jeff, you want to check this out? I think you’ll like it. I showed up to my first meeting as a guest and I loved it. I was smitten. Maybe what I forgot to say is, I majored in business in college with a focus on entrepreneurship and this just spoke to me suddenly. My spirit was alive and also recognized the intelligence in the room with knowledge that I didn’t have, and that business changed. from my formal education years, it evolved. and so the whole startup seems like a different animal. so i joined in a bunch of due diligence. I listened a bunch and just continued on from there and stumbled on my career in the second half of my life.
JP:amazing! That’s a great story. and I like how you were able to take work through your businesses and sell them and then reconnecting but working through this, and looking at all the opportunities and when this one came in front of you, it wasn’t, uh oh, i don’t need to do this. you jumped right into it and started to explore and got excited for this whole new world that you’re now part of. and it’s very exciting because one, it’s innovative. it’s always changing. nothing’s the same. so it just works out pretty cool. So in taking all that experience and the learning that you do have or that you’ve gained from the last six seven years of working in the startup space, how much of this goes back to that first, second and third business that you worked in? How much are you relatable to those times that you were working through? do you find that you really had a lot of what it takes to help a startup because you were like, hey man, i’ve sold the company, i figured out operations, i know how to work tech, i was an innovation guy. did you just feel it was just a natural progression to go into working with startups?
JW: absolutely! mostly in what not to do or i like to say, i don’t know what’s going to work but i could tell you a few things that won’t work. I made those mistakes and learned how to deal with people and manage people and it took me a long time. but they did translate and that’s how I got into it. I also haven’t mentioned yet, but I work deeply with the startups that I do engage with. I also do a lot of mentoring. it’s a little more casual but a lot of times i also dig deep probably a little annoyingly to some of the founders. But I find that those lessons or really what got me into it is when I’m seeing the pitches and hearing the problems or certainly hearing the problems from once I invested and I hear you know, I get the investor reports and such um. I realized, wait, I can help with that. and one thing that just doesn’t sit well with me in startup community or with those of us who mentor i imagine i have an uncle that said what you ought to do and when i hear that it’s very easy for us to, on this side of the game, to sit in our chairs and tell founders what you ought to do. and then you know, we go on our way and we leave them with a pile of problems. I can’t do that. If I see something and I recognize that the skill sets and resources aren’t there, something just to leave particularly an early founder early in the game, there’s something that gnaws at me. it doesn’t feel right. so i need to come in alongside. In particular, if I have the tools to say, okay, let me help you with that. it’s the difference if someone’s moving house or something and say yeah, you know you want to lift with your knees and then just walk away rather than helping him actually lift something up. so it’s just how i’m wired. People are wired differently. so not to poop on any of that, but it’s just something that i can’t sit with and that’s where i felt like, alright, money where your mouth is or at least my efforts where my mouth is and get to work. Well, it brings a lot of team elements into it so you’re at least able to see the problem, see the solution and you don’t want to be participating.
JP:just as you mentioned, from a financial standpoint, you want to get in there and actually help them move and propel forward and you can’t do that if you’re just on the sidelines dictating all the things that they’re doing wrong or what they shouldn’t be doing. so it’s good that you can see that. but you’re also, it sounds like you’re envisioning where that business is going to go. so you’re already playing it out in your mind. and if you’re playing that out, that’s where it’s going to go. you’re just throwing yourself in as one of the team members to help them get it there and working alongside that vision. mostly the only thing i’m very cautious about because i want to give people the space that they had that i had to grow my companies in, i listen to their vision. right now if they ask me an opinion, i’ll share it or i might offer an alternative. But really, I want to enable their vision. and that’s really important to me because if i start putting extra weight or my finger on the scale and particularly if i’ve written enough of an investment where they might feel obligated to listen to me, i try to really hold back because i want them to do the company that they’re passionate about, not the one that i’m passionate about.
JP:Oh that’s a great line. enabling their vision. i think that makes a big difference in investing is that we all can have our own strong opinions and strong ideas on what we think is going to be more successful. but at the end of the day, they’re the ones executing on it. and they just need some guidance and a little bit of hand-holding to maneuver through some of those obstacles. and you mentioned it earlier that even when you were aggressively moving, you still had the opportunity to grow and be successful. and you end up having to shut your business down because you grew too fast and couldn’t balance out that problem which is probably a problem that very few people will have to worry about in building a company. but you’ve gone through that so you can also see those types of things where those growth pieces you can throw and say, hey, you know what you’re working at lightning speed here. you just hired 30 people in 30 days. you know what, maybe there’s some slow down here. you’re going to have a capital call. some issues your burn rate’s high. maybe you should take a look at this or this but you’re still engaging with them. you’re still supporting them but now you’re kind of taking in all of these other pieces that maybe not every investor would have faced in time.
JW: That’s correct. you know when you listen to people you know, even just commonly like how’s business? oh it’s so busy. That’s good. not necessarily right. so it’s very common. When you know more just get more. but it doesn’t necessarily keep you on target. In fact, it can often put you off target. so you’re doing a bunch of sales but it may not actually lead you to where you said you were going to go.
JP:what i like about that is, and we’ve been chatting with um a couple of startups in one particular, what i have learned from the engagement that you’re having with them is that, you’re helping them unearth a lot of things that they may not have actually seen coming and you’re getting them to talk about it. So how do you actually get that? you just made the perfect line which is, ‘how’s business, oh business is great. it’s super busy.’ and then in your head you’re like wait a second, that’s so high level. That is not the detail I’m looking for. How do you get these founders to open up and start to share more of what is that fast problem that they’re having? How can we fix this problem? even though they may not want to share it because they have this fear of letting their investor know that they’ve got these other real problems and because you’re an investor, they’re like, if i tell him, he is going to doubt my abilities. So how do you coach them through that? And I think that’s a pretty needed thing because I find that this happens quite often that founders just don’t want to dive into it and they lack a lot of that good insight that you probably could use to help you and them grow. So are there tactics or ways you open that up?
JW: yes. It’s very old school building relationships. And look, we don’t do it by text. you’re not going to build a relationship. my zoom is awfully hard. So wherever possible, I sit in a room and I spend time and I go first. you know many ways i have years on the founders. you know oftentimes i have years on the founders. the underlying weight of any investment money, although i try not to use that as leverage, that’s like my last resort. and it really is making him feel safe. but the thing is, it’s not an act I put upfront. Alright, I’ll give the founders my failure fee. i want them to know that i’m not, as long as they work in good faith, you know are not lazy, they do everything they can. I said I have a failure fee. It’s a beer. It’s a hug. and it’s Remember me on your next endeavor and that’s the fee. So if you totally screw up but you’ve done everything you can do, I’ll send you an invoice for a beer. actually you’ll take me out for you and that’ll be it. and i wanted to know that you know i’m not the enemy. I came alongside. Your success is my success. we’re working on the same team here.
JP:I had a red button right now. I was using this another show. I’d be hitting it. it’d be like a boo boo bling bling thing. That’s awesome. I love that. that’s phenomenal and i love the fact that you’re risking it all in order to get them to align to one initiative which is enjoy what you’re doing. work your ass off. drive your business forward. I’m gonna be there. don’t worry about me. we’re still gonna do this together and if the outcome isn’t favorable, you know what we’re going to have a beer, we’re going to hug it out and we’re going to work on that next business because i’m going to be your next investor because what i saw in you today is the same thing i’m going to see in your next business.
JW: Yep, I had one other thing somehow buried in there. You know we all talk about sustainability these days and I drive home. if it’s not sustainable to you and your household, it’s not sustainable. so i’ve also watched those balances and then again, it’s authentic. You know I’m sitting here talking about it tactically but, it’s like if you’re working seven days a week, day and night, which is in a crisis, okay I’d expect. I did it. but one of the things i did too is let my health go. I was in good shape and over time, I was very inefficient and not making good decisions. I want it to be sustainable for the people on the front lines. it’s just not going to work if you’re not martyring yourself to your business, not in the long run. you could do little sprints but not in the long run. I hardly agree with that. I think that your creative flow all comes from being able to get yourself outside of your work and outside of the space that you’re constantly in.
JP:you’re right. some good runs where you might do four to six months of a hard run of dedicating focus to move the business an extra notch or two. but really, that next iteration is going to come from the separation of your mind and time. and what you’re actually working on. so it doesn’t mean you have to take a month off. It just means that you need to separate your space and think differently. and you might notice, or i find when i go to a conference and i’m super focused on not the conference, on the business, and it’s because the business has been turned off for that whole day. and now all of a sudden, i’m sitting here listening to all these ideas and talks and all the, ‘oh my god, i’m texting like crazy. we got to do this. what about that?’ and that’s because you’re getting so much influx of creativity and you’re in these big massive rooms and ideas are floating in everybody’s mind. that energy’s high and now all of a sudden you’re actioning things like crazy. so i love that it’s a great way to push your founders to work hard. but also know that they’ve got to play hard too. and they’ve got to get out there and expand.
JW: yep, and you touch on that creative ability, create creative ability in that. It’s a different kind of energy too. it’s an energy that you keep going and going. It’s different from the energy you have to just get up and do the work. that energy drains you. but if you’re coming from that creative space, it sustains you.
JP:agreed. It keeps driving you forward because every morning you wake up thinking, what can I change, modify, clean up, make better, which is part of that creativity side versus today, I gotta sign a hundred documents or I gotta do this mundane job of what I’ve created. So yeah, it does bring a whole different essence to your business. and you’re modeling. Yes, absolutely go back a little bit when you were going through the original businesses and you were in a creative space. you’re in the event space. you’re showcasing people all the time. I’m assuming it will go into bands all the way across and do a lot of big things when you are kind of learning through this. i’m guessing that you probably didn’t think too much or see too much about taking in venture capital and working on that side of it. Do you think that now, today as a venture capitalist, do you think, man, if I would have had this option back in the day, that would have helped me do x? Or do you think you know what I probably didn’t need back then. I’m glad I didn’t use it. But man, do I see the benefits of it today.
JW: um well kind of in between. so my business wasn’t scalable in the way that we talk about scalability. But had I known what I know now, I might have found an angel with an affinity for space. and at the time, you know various points in time, i probably could have used mentorship as well. so that would have been helpful that i didn’t know from me. so all i knew was debt financing. So earlier I had a credit card. In later days, I can do bank loans and lines of credit. but it was really self-financed. and that it stunted the growth. it started the possibility because you get in this middle territory. I don’t know. I think it’s a part of the business pattern. if you’re growing, you’re trying to grow linearly, you get stuck because you need another flow of capital. it’s not going to come from the bank. they won’t lend you that much relative to your history unless you have wealth somewhere else. it’s got to come from venture capital if it’s going to a part partnership of some kind. oh and i love that you say that because i get this question quite often which is why should i raise capital or why do i need to raise capital and there’s always a good group of people in businesses that are always looking for it. they’ve learned through channels or however they’ve built up this knowledge forward. but earlier on when i started, that wasn’t as prevalent knowledge and today. it is out there quite a bit. So I do look at it and say you know, if you’re looking to scale, raise funds, if you’re looking to just grow on a regular 10 a year, and everybody’s happy, then maybe the dollars aren’t really what you need to look for. but i think you just mentioned a couple of pieces and that’s really the coaching, the mentorship. A lot of these pieces all do tie to venture capital at some point because the more you go out and interact with people, the more they’re gonna share their stories and you’re gonna pick up on a lot more of this. So how did this deal work or why did you do this? oh this person came in with this. so i think there’s a lot of lack of sharing. but it’s probably more on the founder’s side for lack of asking questions. but the key thing of course is even knowing what questions to ask alright and until you’ve done it for a while, you don’t know that is true. but what you touched on, i think is important, is the rate of the growth. so if you’re kind of a profitable business, maybe a lot more in the lifestyle category, it’s just you only grow so much per year based on really reinvesting profits and blending and you just, the way i describe it, is if you take a plumber, and plumber’s doing a great business and gets a helper, and that’s fine. and you can still make money and then you decide to double it because business is great. so okay, maybe you can do two of the two vans. two people in each van and you’re doing fine. but as soon as you go to the third, you now need overhead, the person in the office coordinating everything. maybe two people. and now if you don’t go do that, if you don’t go to that next level which requires capital and assuming you can’t get it from a bank, the only way to do it is venture capital. so although otherwise you’re stuck now, nothing wrong with it. if you’re content and making good money and that’s the lifestyle, totally fine. but if you’re looking to build an empire, this is the way I found. you do it. and the other version, i’m actually dealing with this with a company i’ve been in for three years now that the revenues are nice. they’re making a bottom line profit. their growth velocity is slow and you know it’s focused on a positive bottom line. and I was just on a call a couple of days ago trying to explain from an investor’s standpoint when we’re looking to ultimately get an exit. i mean this is too slow. and in this case, it’s really about the brand, not the product that they’re doing. it’s like the brand’s not getting out there again if we’re worried about the bottom line. they’ll never have enough velocity. it could just keep going, just the margins are not that. they’re good. they’re not great. and it’s just a vc game. they’re kind of sustaining themselves so that they don’t have to keep going and trying to find loans or dollars from the banks. but they’re not also accelerating themselves at that 10 to 30 percent month-over-month growth or whatever seems to be the best positioning for them because again, their overhead costs are probably too high. so there’s a fine balance that they’re trying to manage to keep cash flow positive. well there’s that. but in this case, it’s not even a bank for lending. they’re definitely investable. it just needs a little tweak in the business, in the vision or in the plan actually. The vision is the same. you know once it will be. you can get it quiet. but it’s just a tweak in the plan. It’s just a little shift in thinking and that comes from again, as you mentioned, the knowledge and understanding of our coaching and being able to have that conversation. and you know some things don’t always register until you hear them a few times. or you don’t really dive into them to understand them until they’ve been brought up a few times and then you start to think, oh man, you know maybe that is something i could do or that’s something that i could get behind. If I had the right coaching or the right mentorship supporting me so that I have more confidence in my ability, that if I took this half a million dollars, I could convert that into three million in business.
JP:this has all been really great in understanding how all of these have shifted and how you put this emphasis on the startups and helping them today. now going back again to let’s say the company that you sold in 2015. what was, as you kind of progressed through that and made that decision to sell and move forward, what was maybe one thing that got you decided to sell that? you weren’t like was it the passion changed? was it, ‘i got introduced to investing and thought you know what, maybe they all kind of coincided at the same time so maybe this is something i want to do.’ What kind of got you to make that move and decide that this was the right choice and next steps?
JW: well if i touch on the metaphysics, the stars align. So two couple things happened. One, my latest and supposedly greatest key employee, the latest hire um which you know have had a number of them over the years, highest salary ever paid, our deepest resume i’ll grant, but a few months in, he got an offer honestly i couldn’t compete with. and i couldn’t blame him for taking it. He got an offer to go on tour with a big name as a lighting director and anyone in that space, in that field would have said yes. so he did it the right way and everything was great. He gave me enough notice, kept me in the loop, all done right. but i just got tired of onboarding people. so from that, i was just like, i can’t just do this again. i’ve done it so many times where the next key higher and the their own last and you know in the earlier days, i kind of said, i might be the world’s worst employer or is something you know in the industry or in the circumstance that you know it’s just draining me and draining the business. In just this turnaround, maybe in the early days, I wasn’t a great employer. but i’d like to think i got better over time. The second thing was my friend leaving his day job and building this company and that just opened up an opportunity. and the third thing is that, i had some real estate in New York City. and my brother and I own it. we got an unsolicited offer to purchase for a price we couldn’t say no to. so i had the liquidity that i didn’t previously have. so you know the way i say is, i can’t eat bricks. I had to keep working because the welt’s on paper. and it was income but a kenny bricks. and you know the side story is that a mortgage wasn’t an option. so those three things happened maybe within about 30 days of each other. and I also recognized that the game I was playing was a younger person’s sport. I was in my 40s, still good but my bounce back wasn’t what it was in the 20s and 30s. And I just knew for health reasons, you know, it just seemed time.
JP:Well, it’s great that you were able to kind of align the stars as you mentioned but maybe there’s one thing there that you were a great employer because everybody was being poached from you, which means that they obviously were learning a lot and the credibility came with that. so that’s a good thing because one, you’re showing that you’re putting out top talent. That’s a pretty big thing to have. but i also like the fact that you noticed that there is a point where if you were being drained of top talent all the time. Maybe this was the right time to kind of sell and move yourself into a different position in your business. but because of the fact that you saw that the market was building up, it is a good time for people to move faster. Having you as the business would have obviously made someone go even quicker and better into that space, so a great venture capital opportunity. so i think it actually worked out quite nicely in the sense that you were able to pick up on all these things. and the reason why i was diving into this is because we don’t ever get to talk about this. and it’s very rare that a founder knows when to sell. a lot of the times they sell when things are bad or when they’re down or they merge, when they’re just tired. but they haven’t really found that space that they should be working in. so it’s good you found the space. you realized it. you moved forward and you had a lot of great things that all happened at one time.
JW: Yes, there was a bit of that but you give me too much credit. Yes, some of the employees I had were that many. it’s a transient sector so it was also circumstantial. but thank you for the flattery.
JP:Hey, no worries. I just caught it as I saw it. But I think at the end of the day, what’s great that comes out of all of this is that it puts in the mind of a founder that opportunities come and you always have to be open-minded to them. I think a lot of what you talked about is of course, there is a real significant opportunity in any space that you’re in to one. sell your business to merge into other companies but that all comes from empowering yourself by reading and learning and paying attention and being hyper focused in a space because that’s what’s going to allow you to catch these types of things and be able to jump in and out when you need to. and i think a lot of that does get lost i think. a lot of times founders don’t find the right opportunity of when to sell and they could end up losing it all because they didn’t take that option. and you can look back at the most popular ones of all time which would have been like yahoo when they were offered to be sold for a massive 50 billion dollars or something and chose not to take it. and then went down to some crazy number of like 700 million of evaluation to work their way back up again. but i think a lot of the times, we get too stuck in our own world. and we forget that listening and opening ourselves up can really help drive home more information which can enable you to do better things for sure. and this is where i think what i’m hearing, not that at all, not that any team’s immune from what i’m about to say, but the importance of a board. and I do mean a board, not a rubber stamp board. and whether it’s a board of directors or board of advisors, you know i don’t care what label you give it, but that you founders have a team of wisdom. That’s a question I’ve asked in a couple of early interviews where I felt like the founders were a little young. But I asked him where the wisdom was. I’ve had responses of where’s the knowledge? I said no. Where’s the wisdom and that’s the key. so also to be able to listen is key. The very key thing is the ability to listen and look. a board can get it wrong. you can ask. You know three advisors, they all tell you to don’t sell and in hindsight, it was the wrong decision. but at least you’re getting some back and forth. and because the founders, even if you’re surrounded by people, it’s a very isolating position. you’re making these decisions and after a while the objectivity disappears. it’s just natural. It’s just how our psychology is. So having some people that are one foot in, one foot out, maybe some people that are all out, it’s helpful to get those perspectives.
JW: Oh, I support that 100%. anywhere you can get information and insights and take them back and i think it’s not so much about just taking the answer and doing it. It’s taking a lot of answers and trying to figure out what the solution is. Where do I want to be? How do I focus? How do I build to the next stage? Uh, we have one startup where, you know, they’ve successfully done their five-year plan and now he’s like, if you gave me 50 million, I wouldn’t even know what to do with it because I can probably figure it out. but we don’t have to plan. So now, we’re going to work on our plan. so we’re working on that right now. so that we can figure out what the next five years looks like. and i love the fact that even though the plan is going to shift, change and go in a different million ways, it’s that they’ve put something together to get them the next five years and then they can iterate, pivot, change but they’re putting that in structure and they’re going out to their investors, they’re going out to the community and they’re asking questions and they’re getting them to give them information that they may not have gotten by just being in that space. and I think a lot of those types of things help generate enough value so that you can kind of go back and see what sticks and what was on the wall and kind of disseminate that down into a real plan, and then say, okay, this is our plan. it’s 90 there. we’ll maneuver in between it but, let’s create our own parameters and go forward. Sure, but there’s one thing you said that I am drilling down and some real nuance. That’s important to me. so getting information from a whole lot of places can also get very confusing and perform analysis paralysis or just confusion and so on. So I think it’s important for a founder or founding team to make decisions as far as possible on the criteria for assessing information. so i know it’s a little multi-dimensional here but you know, there’s a ton of us that will mentor. and i tell people, i don’t know if my mentorship, my information’s any better than anyone else’s. I really don’t. um, but if whoever I’m talking to has an outline or a decision tree or something on how to disseminate, how to process that information, what to discard and what has merit, that’s really important. after that, the information, youtube all you want right, you can find it out there. or I touched on wisdom. it’s not the information that you or i may have. It’s our particular experiences in application of the information that might be relevant to that circumstance.
JP:I like that it’s a lot deeper and you’re right. The paralysis can occur from too much but if you can figure out how you rank or score that data or that information to get you into the right position, then taking that in won’t be a bad thing. you have to limit yourself on how much you can also take in but there is going to be a good positive outcome that once you’ve isolated that and understood the market where you can potentially go with, it actually just keeps score. so it’s both quantitative and qualitative and that’s the art and science of business. I love it. Um, alright. well now we’re going to kind of shift a little bit and we’re going to shift into, being that you’ve worked with a lot of startups and a lot of founders over the years, there’s probably one story that just probably resonates with you on what it takes to be a founder or what it takes to be an entrepreneur and we’re kind of looking for that heartfelt story where you’re like, i can’t believe they made it this far or what an incredible journey these people have been on. Is there something that just pops in your head? We kind of like to just share one of those real heartfelt stories that just blows your mind on what it takes to be an entrepreneur?
JW: Well, heartfelt. I don’t know. Let’s see if we could tie it together to the question. but there is one story in particular to me. there’s an example of just great human capability in it. so one of my early investments i went into. There were two founders and they came in fairly early in the game. but it was rough. they were much more on the technical side of what they were doing than the business side. That was a situation, an early situation. I said I can help with that. so i tried but the founding team i think wasn’t quite ready to hear it. they knew better. So a few events occurred and I realized I had to distance myself a bit without getting to the ugly side of things. but let’s just say some money and lawyers got involved, not my first choice. it’s actually my last choice and they pushed me to my last choice. It was ugly. It pushed myself to levels I never wanted to go. but it’s good to know I’m capable of doing it if I have to defend something. That said, it all resolved very well actually. Just before it was resolved, wait, I missed the key part, so I have a spreadsheet where I track my investments and I wrote in the notes column expected to be out of business in 2017. Then 2018 came and I just deleted the seven and made it an eight. Then, at that point there was resolution to our conflict and I got the backstory and one of the founders needed to partly depart and make peace with the other founder in the subsequent years. Not only has the company developed beautifully and the team beautifully, I mean this is now what I consider my flagship investment. I am so thrilled to be part of this company, to be part of the story. it’s just amazing and actually i just made my fourth investment in the company. so it’s not just that it’s like i’m there. I’m in it. I absolutely love this company but I also absolutely love this founder. So heartfelt, we can go from what was in the territory of the worst business relationship in my life to a beautiful human relationship and a really good healthy business relationship as well. and then my wife jumped into the conversation. she’s on board with this company and it’s just like we’re just having a blast, just cheering this company on, helping where we can and just loving it. but this was at the point of you know, like disaster and uh, and ultimately, i was able to delete that cell on my spreadsheet and say, oh that’s awesome.
JP:oh, that’s a great story. So did you find that the connection was really with the founder that eventually as you kind of worked through all this and reconnected and cleaned all of this up to make it a success? Did it really just all of this come back down to that one founder that just had that true conviction to make this successful and eventually overcome the barriers that were in front of them?
JW: yes, i think it’s hard to know before you dive into something because you don’t know but having a two-founder team where both had very different ideas on how to make it happen, i could tell you now that i know the story that one who’s no longer there had ideas that won’t work territory. i have very few of those things because it’s more like, well how can we make it work is more my attitude. but that was one of those that won’t work. Yeah, you don’t get to not show up and still make a gazillion dollars.
JP:exactly. No, that’s awesome. That’s a great story and it really happens when you have one founder, two founders or board advisors, all the above. There’s a lot of work that has to go into to balance out all of that and being able to get behind and support that one direction or that one execution play can make a big difference and can break or make your company. well that’s a great story and this was a case of just step by step, cleaning up the messes. now that there is clarity on where to go and it takes a little time. and this is a technology company so it goes slower than a cpg or something like that. but it’s happening. oh that’s amazing. well congrats, and very excited to hear more about their success. I think that’s a great story and hopefully they talk about it a lot too. so alright we’re going to transition into our rapid fire questions, okay?! on the business side, first question. founder or co-founder?
JW: founder or coach, oh, uh co-founder.
JP:unicorn or four-year 10x exit?
JW: four-year 10x exit.
JP:tech or cpg?
JW: cpg.
JP:brand or tech?
JW: brand.
JP:ai or blockchain?
JW: blockchain.
JP:first time founder or second, third time founder?
JW: second third.
JP:first money in or series a?
JW: first money in.
JP:angel or VC?
JW: angel.
JP:board seat or observer?
JW: observer.
JP:safe or convertible note?
JW: convertible note.
JP:lead or follow?
JW: lead.
JP:equity or interest payments?
JW: equity.
JP:favorite part of investing?
JW: the adventure. There is an adventure. It’s pretty awesome.
JP:number of companies invested per year?
JW: three to four.
JP:preferred terms?
JW: uh preferred terms, i mean convertible note in that. plain vanilla under there okay.
JP:uh, any verticals that you focus on?
JW: cpg and sas.
JP:good choices. For Startups, what are two things that make them stand out if you were to invest or what two things do you look for?
JW: Again, two things. team chemistry including me with it. and unique insight into them into a sector or market space.
JP:I like that. Lastly, team’s always number one which I agree with but I like that unique setting which I guess is their differentiator.

JW: right, it’s knowledge and power because it makes a difference. That’s right. Yeah, I mean if we’re done, I can qualify that a bit.
JP:yeah go ahead.
JW: yeah you know, how many do we see that says, this is the only such and such in the space but didn’t you just see two of those last week at those pitch events? and on one hand, you know people are running stealth early. On the other hand, you know really what’s the difference and if someone has a really unique insight, that’s that, you know, quiet in the corner and observe the type of scenario where you just see an angle to it. that just isn’t obvious at first glance. That’s really interesting. Yep, I agree. that’s all part of that whole focus, how focused are they, how much do they know, how deep have they gone with this? that speaks in volumes.
JP:no, I like that. Yes, okay. personal side. book or movie?
JW: book.
JP:Superman or batman?
JW: batman.
JP:pizza pop or ice cream bar?
JW: say that again.
JP:pizza pop or ice cream bar? It’s pop.
JW: Is that a Canadian thing? I don’t know what a pizza pop is.
JP:it’s one of those, you’ve never seen a commercial for a pizza pop? they’re like the poppers pizza things and they pop and blow up everywhere.
JW: Okay, and what’s the other one? the ice cream bar? I’ll do the ice cream.
JP:Yeah, um alright. five minutes with Bezos or oprah?
JW: oprah.
JP:Arsenal or Manchester united?
JW: arsenal. out of my realm.
JP:or so we can skip that. they’re football. so the English Premier league. yeah or something looking for an arsenal. Oh, you need soccer. I’m looking for Arsenal fans. Bike or rollerblades? like big mac or chicken mcnuggets?
JW: oh, I won’t touch any of them. but if i had to, big mac.
JP:alright. trophy or money?
JW: money.
JP:beer or wine?
JW: beer.
JP:hotel or hostel?
JW: hotel.
JP: king or rich?
JW: rich.
JP:I like it. Alright, okay. Now, getting down to the final few here. What is your favorite sports team?
JW: Well, I’ll go with the last time I paid attention to sports. I’ll say the New York Yankees but I really follow sports. Yeah, it’s interesting. it’s shifted a lot but because it’s part of that social norm that keeps everybody talking and interacting. you kind of stay on the surface. you still learn a little bit here and there. but it’s a tough one when you’re not able to go to any matches. but yeah, that’s not something i missed.
JP:favorite movie and which character would you play in the movie?
JW: ah favorite movie is still Return of the Jedi.
JP:I love it, yeah.
JW: And uh, I think I’m in the R2D2 mood at the moment. That might change to Chewbacca or C3PO, but I think R2D2.
JP:I like it. That’s awesome. favorite book?
JW: favorite book. i think, at least also at the moment, oh actually you know what i got one that’s out there. Oh, I’m blanking, Dr. James Hollis. he’s a Jungian analyst and oh I am blanking on the spot. but uh finding meaning in the second half of life. and i’ll just say, instead of a midlife crisis, it’s about the middle passage, finding meaning in the second half of life. I’ll give you a second choice though. “Hitchhiker’s Guide to the Galaxy.” I think I read that one a long time ago. Well, the original. The BBC television version is great too. It is so poorly produced. it’s funny, i can’t remember that i’m gonna have to look that one up again, not the hollywood movie that came out some i don’t know 15 years ago whatever. the BBC version, fantastic.
JP:Okay, um alright last question. What is your superpower?
JW: my super power, i touched on it, really is the observation of human behavior. I’ve noted here along the way, paying attention to psychologies because at the end of the day it’s such a huge part of why we do what we do. It’s part of our biochemistry, how humans work and the ability to observe that and see in between things. so, it sounds out there but whatever the flaws are played or I guess you know thyself. and once you know thyself, you start recognizing things externally, become really interesting. so the superpower is to find those interesting things and observe them and communicate when asked.
JP:I like it. well it’s a great superpower to have and i think a lot of people probably could hone in on that superpower themselves. but being observant and looking for the anomalies and looking for things that stand out in a crowd always makes a big difference. and especially in the angel vc world, it makes a huge difference because that’ll make or break your investment. So I think it’s a great thing. But, Jeffrey, I want to thank you very much for all of your time today. As I always do, I took lots of notes. Okay, I’m old school in that sense. But, I always have to write these things down so that I don’t forget them. But, amazing. and then we learned a lot. I love what you’ve done and the things that you are building and how you’ve got to today. and kudos for all the coaching and mentoring you’re doing with startups. It’s huge. keep that up and the way we like to kind of end our show is we like to give you the last word. so anything you want to share to the investor or to the startups, i turn it over to you. but thank you very much for sharing today.
JW: yeah, well first, i’ll say thank you for hosting and inviting me. and this is a great process. I love it. It’s part of what makes this whole space so special. so appreciate it, thank you. and i think what i would leave with is, don’t lose perspective. This is an adventure. This is how entrepreneurship and a startup works. it’s how we explore life, whether it’s in business or sports or the arts or whatever, it is. but keep the perspective that your life is bigger than your business.
JP:I like that. I have all these lines I’m gonna have to use.
JW: for you man, go for it.
JP:Well again, thank you very much jeff. I was trying to write all that down. I’ll do that after but again thank you very much for sharing a phenomenal job. just give us one sec but thank you. that was a great conversation with Jeffrey Werner and one of the things that really stood out for me is when he talks about working with a company that he’s made an investment into and what he ends up doing is you know the failure fee. and i love that it’s a beer, a hug and that he gets the opportunity to invest in your next company. so i just thought this was so well thought out that you know what, hey, i’m on your side here to help you grow your business. and if for any reason something doesn’t work out the way we all expect, then here’s kind of your route. you got to buy me a beer and we’ll talk about it and work on that next venture. so really cool. I like that he goes into sustainability. Authentic. He is making them feel safe, enabling them to envision their vision. so not going in and trying to change the model but going in there and providing enough insight that gets the founder excited to have the investor on board and then again just looking for those unique opportunities and ways to drive into that business. So Jeffrey, thank you very much for sharing that great insight.
JW: always a pleasure.
JP:So thank you for joining us today. If you enjoyed the conversation please subscribe to our YouTube channel or follow us on Spotify, Apple Podcast and or Stitcher and you can also check us out at or for startup events visit thank you very much and have a great week.

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