Investing Impatiently: Lessons From a Serial eCommerce Entrepreneur
November 16, 2022
May 10, 2023
min read

Investing Impatiently: Lessons From a Serial eCommerce Entrepreneur

The Profit Forecast: The eComm CEO's Podcast

Episode #13: Jack Dreifuss of Impatient Ventures

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Ben Tregoe: [00:00:00] Jack, great to see you. Thanks for joining the BA Bridge podcast.

Jack Dreifuss: Yeah, nice to see you too. Thanks for having me.

Ben Tregoe: You know, the term Polymath gets used a lot, but I think it applies to you especially. When you look at your LinkedIn, you look at your background, you do so many cool and interesting things and I can't do justice to it.

Ben Tregoe: And I wouldn't do justice to it. It would be awesome if you could kind of give a little bit of your background and what you're working on particularly now.

Jack Dreifuss: Sure. Yeah. It's funny, I was just talking about Polymath yesterday. I think that in the beginning stages of a startup, it kind of requires a sort of polymath type operator.

Jack Dreifuss: So I wouldn't sell yourself too short as the CEO of a seed stage startup is, you know, the kind of colloquial way of saying wear many hats is maybe more in a fancier way as being a polymath. So I think that for me, I've always enjoyed the early sort of stages of, building a company that require a lot of.

Jack Dreifuss: You know, hat wearing or, you know, skill sets. And so you know, starting back from moving to San Francisco and working in technology startups, it just, you know, the beginning days require you to get your hands dirty in a lot of different ways. And so for me, it tended to be more about growing the company.

Jack Dreifuss: And that comes in kind of three flavors as far as I see it. One, you gotta have the, resources. So raising money two, you gotta have the. The, sort of people necessary to build the product and service the product. And then three is ultimately gonna getting customers, so business development.

Jack Dreifuss: And so kind of all of them, I'd say center around one particular type of science or math, which is storytelling or you know, storytelling such that then things happen as a result of your storytelling. And so I've always enjoyed that and the variety of flavors of recruiting, fundraising, and sales, and.

Jack Dreifuss: That's the kind of philosophical high level. But then more specifically what I'm doing today is historically speaking, I had been focused on building one company. And so, you know, most recently in the e-commerce space, I was the chief strategy officer during the early years of Before that, I was at a different enterprise SaaS platform, building out the sort of early go to market.

Jack Dreifuss: And so for me I'd always kind of had the itch to work on a lot of different things. It was never enough to kind of just be working on a lot of different lines of business within a company. I always liked working on different projects, different companies, and different ways, whether it be a services business or a product business.

Jack Dreifuss: And so finally this year I kind of broke free from once being very focused as a, you know, founder or as an early stage employee on one company. And now I'm doing everything from, I have an a venture fund called Inpatient Ventures. I have a consulting practice where I help early. Precede and seed companies kind of get to product market fit, get to their next stage of fundraising called inpatient consulting.

Jack Dreifuss: have a performance marketing agency. I'm doing some small m and a work, and I always feel kind of i, feel sheepish sort of or, or I hesitate to talk about working on so many different things, but for me, I get more energy and I'm more motivated and I'm more excited and I work harder and longer and I'm more focused.

Jack Dreifuss: When I have several different things going on at the same time.

Ben Tregoe: Did you always know that about yourself or was that something you discovered?

Jack Dreifuss: Yeah, I mean, it, it definitely, it goes all the way back to not wanting to do my homework and wanting to, you know I, was a big poker player growing up. I played a lot of online poker.

Jack Dreifuss: I was an athlete. I played a lot of different sports. You know, I was, at one point I was a competitive risk player. If you know the, you know, the world, the what? There is such a thing. I didn't know that. Yeah. There is such a thing. So I, think I've always gotten excited when I could kind of bring ideas from, you know, one conversation and with, amongst a group of people into another conversation.

Jack Dreifuss: And so I've always like kind of moving around people and ideas and so yeah, I've always, I think, been that way and so, . Now I finally feel like I've gotten to a place where I've had enough of a career, so to speak, you know, 10 years in to, to have enough access to be able to work on a lot of different things with a lot of different people.

Ben Tregoe: Yeah. know, as you were talking it, sort of made me wonder, because it's a great fit for you, this ability to do a lot of different things and, you know, you're energized and actually more focused as a result of it. I think there's a lot of founders share that, you know, that kind of like, you know, can go in a lots of different directions and they enjoy that.

Ben Tregoe: But you think that founders over-indulge that or is there a way to, [00:05:00] do you see them making mistakes in that or are there ways for they, you know, tips for listeners to

Jack Dreifuss: channel it better? That's a hot topic, right? So I think in, you know, the kind of 20 20, 20 21 super hot sort of ended.

Jack Dreifuss: Decade bull market we were in, I think it became popular for multi-company CEOs, you know, CEOs that also had venture funds. You know, I think taking on the CEO position is a particularly nuanced thing where part of it isn't just the time you're spending on it, but also part of it's your ability to motivate the people that are working, you know, for you, with you.

Jack Dreifuss: And so I think part of it can be an image problem if you're sort of. You know, the the dad that's raising several families, it's kind of hard to get your kids to, you know, really take you too seriously. And so, you know there's, and there's a whole subset of people, obviously, you know, the Aubrey Marcus followers that kind of believe in this sort of, speaking of polymath poly lifestyle of Yeah.

Jack Dreifuss: That I'm, I'd say that I'm a more of a traditionalist and believing that, you know, good parenting comes with being able to really have your kids be able. Know that you're there for them, you're gonna guide them, you're gonna protect them. You're gonna, they're gonna trust you as a result of that. So I think as a CEO, you're sort of in a coveted role.

Jack Dreifuss: You know, I think CEOs who also invests, whether it's angel investors or maybe they have a small fund, cuz their investors wanna capitalize them to just casually have their existing social relationships be able to be investible. Right. Which was a lot of how I got into investing as a founder. Connected to so many different founders, and it was a very natural process to go from investing my own money to investing other people's money into the deals I had access to.

Jack Dreifuss: But, you know, it's a very bit interesting question. I've I've, been working with a friend that's working on a talent marketplace around, you know, there's the, also the big sort of controversy around the the engineers that were getting second jobs. Yeah. That, And so I think the really interesting question is that in the remote work, Where people aren't needing to commute into work, they're not needing to be at their desk 24 7.

Jack Dreifuss: Could it lower the cost of your, you know, I guess I'd almost throw the question back onto you. I mean, you're an early stage startup. It's hard to say this, but if I could tell you, I could cut the cost of your engineers in half by saying, hey, they're, you're gonna allow them to get second jobs, but they're still full time getting their job done, executing.

Jack Dreifuss: You know, would you be open to that as a CEO of potentially, you know, multi job? Multiple employed you know, team on your side. So I would flip it and ask you, would you be okay with, your employees having second jobs if it may lowered the cost? No. Yeah, no.

Ben Tregoe: Cause I think that particularly at our stage, you know, we're six people, you know, maybe we'll be at 10 by the end of the year.

Ben Tregoe: You, just gotta be all in. And so I don't believe that there's this like idea to like, Oh, you know, I work 40 hours for you and then I work 40 hours for company B. Like, I want to know that somebody is willing to put in 60 hours or more if, we need it, you know? And also I, also don't believe.

Ben Tregoe: You know, if you're really working hard, it's taxing and you need downtime. So I don't want somebody, you know, to be like taxed twice and then they have no downtime. So my theory on it would be that I'm getting, you know, 75% of their quote unquote fulltime effort. But, you know, maybe that makes me, you know, I probably just like eliminated a.

Ben Tregoe: Raft of engineers from ever working ?

Jack Dreifuss: Well, yeah. I mean, Don, I'm a big fan of pulling some of Don Draper's points of view from, Mad Men, which is, you know, when asked kind of how do you come up with your best ideas you know, he says, he goes and watches a, matinee right. So his mind's completely off the thing he's trying to solve for.

Jack Dreifuss: So it's like, you know there is that delicate sort of subjective line in the stand of like what is considered work outside of Your full time sort at wt shop. Yeah, so I think that like in a world where you can enable employees to get their work done and then go, you know, do a Pilates class in the middle of the day, or go, maybe they've got some kind of advisory work where they're helping some other startups in a particular area.

Jack Dreifuss: They have a skill set. Yeah. And I think that ultimately the same. I think we're in the era of kind of, I would say post, we're in the, I'm gonna coin something here. We're in the post vacation, you know, employment era where I think it used to be you just work really hard nine to five every day, and then you take your two.

Jack Dreifuss: Yeah, whatever. And I think that's kind of a fluid thing now where really it's meant to be like, how can you take kind of vacations, but they don't necessarily mean you're flying to Tahiti for a week, but you know you're, going and, doing like a, some sort of a workshop for a weekend or you're helping your buddy out with some marketing materials for his new agency business or whatever.

Ben Tregoe: Yeah. Very Churchillian. [00:10:00] That's what Churchill would do. He would, he had all these d. Efforts and activities and workflows. So like when he was done doing one thing, you would, you know, he was like a, build brick, walls and paint and do all these different things to keep it, you know, But he very rarely just took the vacations and hung out.

Jack Dreifuss: So , Yeah, it's definitely not my speed. I, will occasionally get motivated and I'll go and, you know what I like to do, especially I've finally started to take advantage of the remote work era. I'm gonna be in South America for most of January, but I'm gonna be working the whole time. Yeah. I got a friend who's from Argentina and I'm taking advantage of the opportunity to be local with a local or be in, excuse me, be in a foreign country with a local but I'm gonna be working the whole time.

Jack Dreifuss: And for me that's a, it's a form of vacation and that it's just an environment change. Yeah. And so I'm super excited. I, did that, I tested that by, with a little bit of difficulty cuz of the time zone. I was in Spain and Portugal in June and, worked, you know, five hours a. And then of course I'd indulge a little bit more on, you know the, eating out and the drinking and whatnot.

Jack Dreifuss: But, you know, within reason. And so I, struggle to be the type that like has an away email for a week and doesn't talk to anybody. Right. Yeah.

Ben Tregoe: It's hard. Really hard. It's hard.

Jack Dreifuss: Yeah.

Ben Tregoe: Hey, so you know it, I wanna talk a little bit more about Impatient but before the vc, but before we do that, it struck me that you see.

Ben Tregoe: Companies from multiple angles, right? So like as the vc, you're seeing them as like the recipient of the pitch decks and you know, putting on their best face, right? As the consultant, you're now like, oh, I'm actually behind the curtain. And like you know, this is messier than is presented, you know, in the deck.

Ben Tregoe: And then on the agency side, you're seeing a very specific part of, you know, the customer acquisition. I mean, not necessarily all three in the same.

Ben Tregoe: That's cool. Yeah. Yeah. So what do you, know, given those that you get these like really unique angles cause that's like nobody gets to do that. What do you see are, or like maybe common traits of success or common mistakes?

Jack Dreifuss: Yeah, good question. You know, again, going back to what I said earlier, I sometimes feel a little embarrassed.

Jack Dreifuss: I always kind of scoffed at the people that were like, I'm. Private equity, m and a venture capitalist, you know, serial entrepreneur, whatever. Everything for me was really organic where I was kind of, you know the, investing stuff was organic. The same way starting a company. It was just I didn't force anything before it felt like it was sort of ready to blossom, so to speak.

Jack Dreifuss: And so I've been fortunate by being perhaps a little bit. Risk tolerant bordering on careless early in my sort of twenties, that allowed me to make a lot of mistakes and, you know, still survive the other side of some, of the fallouts from those mistakes called having loving parents and good friends that allowed me to kind of make mistakes early and, recover.

Jack Dreifuss: And so I, you know, I think that that arguably, I would say is a good characteristic of a, of kind of the, early. Founders and employees at a startup are willing to make mistakes and be able to recover. So some people call that resilience. Some people call that being dynamic. I mean, there's a reason why the word pivot is such a common, you know, almost cliche word in the early days of a startup.

Jack Dreifuss: It's because your every day is arguably a, micro pivot where you're taking in new information you didn't know yesterday, then having a count to how that shapes your product roadmap. Customer acquisition strategy, your customer retention strategy, your partnership strategy how you're thinking about your marketing, how you're presenting the company, who's working on what and how.

Jack Dreifuss: And so, you know, I'm a big fan of the Lean Startup method. In fact, I was just talking to, as you know, Patty on my team at inpatient consulting about that methodology. I think that's a hundred year methodology. I think that the idea, if you're not familiar with the book Yeah I, highly recommend it.

Jack Dreifuss: You know, Eric. Who is kind of a early agile software adopter in the kind of, sort of modern day Silicon Valley, where it's how do you, take the, how do you, how are you the most efficient and the least exhaustive in terms of going to market with some sort of a plan, whether it be a a, sales plan or a product plan such that you can not get bogged down by exhaustive planning and then be able to put a plan in action to collect data to iterate right iteration.

Jack Dreifuss: Iteration is kind of like the the dynamic evolution of pivot, which is you take in information that then changes your perspective on how you see the business and how it should best be run. Yeah. So I think that [00:15:00] quality of, being able to being, willing to make mistakes and not allowing the kind of natural outcome that all humans experience, which is letting your emotions kind of either prevent you.

Jack Dreifuss: Making mistakes or letting those mistakes, you know, boggy down for too long. Right. We are ultimately an imperfect sort of system of, operation, right? Being that we're emotional. So I think that the ability to, and again, and this is where it gets into kind of the, Buddhist sort of way of looking at it is being okay without any outcome and now not allowing a negative outcome or a positive outcome to.

Jack Dreifuss: Too, much to either side. You could have a positive outcome and then you could end up doubling down on something that once you double down it doesn't work. Maybe work the first time. It doesn't work the second time. Right. Or something doesn't work the first time. Right. Whether it be a sales acquisition strategy, a marketing a media plan a marketing campaign a fundraising strategy.

Jack Dreifuss: Right. You, just went through this process yourself. Yeah. And probably dealt with a lot more. Then yeses in the fundraising process. And it's so easy to get discouraged and you hear this time and time again, the Airbnb story being the most famous, where it was like 99 no's and one yeses, and you know, now it's a hundred billion dollar company or something like that, right?

Jack Dreifuss: So I think now getting bogged down by the no's, you know, making early mistakes, not getting too emotional about it, and then continuing to stay agile so that you can, you know, continue to iterate and improve the efficiency and, and give yourself the. Access to opportunities early in the life cycle of a company.

Ben Tregoe: Yeah. That's fascinating. It's, there's a lot there. So I kind of want to dive into one of the first parts, like, you know, the, that Buddhist philosophy is, really interesting because I was thinking, you're like, well, not being afraid to make mistakes for a lot of people, that's very difficult, right?

Ben Tregoe: Because their ego is so tied. That the outcome has to be right. So then they get caught in this process of like well, we're not ready, you know, maybe to your point, like over planning or not getting the product out there, so is it just removing your ego or is it sort of coming to the realization that like, nah, you know, I'm okay with the outcome.

Ben Tregoe: Like, how do. Get past your fear of failure, .

Jack Dreifuss: Yeah. Another interesting topic I've, spoken about recently with, some friends is I don't think it's about removing the ego. I think it's about discerning between what I would maybe simplistically call good ego and bad ego. Okay. So good ego is like you get up in the morning.

Jack Dreifuss: You're motivated to get up in the morning. Like if you didn't have any ego, I think you'd just kind of lay in bed all day. Right. Right. You wouldn't really have a reason to get up. You're like, All right. I believe there is a, you have purpose, right? Positive ego is typically pretty align with purpose.

Jack Dreifuss: Yeah. Like I believe I'm capable of being useful and offering something to the world. I believe my skill sets are, worthwhile. Yeah. I believe my opinion matters. Right? I think bad ego is. Believing that version of your ego today of what you believe is a good opinion, a good skill or a purpose or a meaning is gonna stay that way forever.

Jack Dreifuss: I think that in the world of continuously evolving yourself, right, and that's again, going back to the making mistakes early, taking information it takes, an ego to make a mistake in a way. Like, again, I think ego is often seen as a very binary thing, good and bad, but I think there's a version of ego.

Jack Dreifuss: You had enough conviction and enough confidence to make a certain decision, and then maybe it didn't work out. And so the good ego allowed you to both make that decision and then you then had enough you know what's the way call, call you? Had you had enough of and then you had a lower on the bad ego that you were willing to both emit the mistake, admit where it was wrong, take in new information, recalibrate.

Jack Dreifuss: Yeah. I think it's a distinguishing between good ego and bad ego. Good ego is dynamic. It's, resilient, it's dynamic. Bad ego is very stagnant, very stubborn. Only staying that perspective you have being unwilling to

Ben Tregoe: change. Yeah. answers my second question, which was like, how do you recover from the inevitable mistakes?

Ben Tregoe: And it sounds. Don't let the bad ego.

Jack Dreifuss: Don't let the bad ego. And I think part of that too is I think bad ego also doesn't know how to ask for help. Good ego does. You're confident enough that you're willing to go ask somebody for their time. You're going to willing to ask somebody for help. A lot of times people are afraid to ask for help.

Jack Dreifuss: I've been somebody that early in my life sought out mentorship. I mean I, think I emailed the LinkedIn CEO when I was in college. He [00:20:00] didn't gimme the time. I was willing to kind of go and that arguably borders on arrogance. But, you know, I was unafraid to kind of get into rooms before I maybe was, you know, qualified by whatever standard society looks at who's, you know, merited to be in a room.

Jack Dreifuss: But, you know, I cold LinkedIn, I cold called I, asked for introductions to get people's times so that I could learn how something works to get a job that I wanted or to get an introduction that I needed. And so and I try and. In the spirit of kind of all that I took from the world, trying to offer that back so that whenever I get asked for help or whatever I, you know, of course I'm evaluating the person who I'm not just gonna open up my Rolodex or Right.

Jack Dreifuss: Whatever my time. But I think that the kind of what goes around comes around sort of like reciprocal nature of like being a good actor and paying it forward. You know, I think that relates to good ego versus bad. And so I think a big part of this, Being able to recover from mistakes is partly in your own humility, but then it's also having the necessary people foundation.

Jack Dreifuss: Yeah. I your own foundation to be able to recover and get support where you needed to. And some of that time in my life was failing at my first startup and having no money and having to sleep on friends' couches. I mean, it was like I lived that very. Cliche and it was intense. It, sounds kind of cool in retrospect that I did, I worked out of a garage, failed and then was sleeping on friends' couches.

Jack Dreifuss: Cause I couldn't afford rent. I would never recommend that to anybody, . But I was very lucky in my life to make some crazy mistakes. And then, I mean I, have, I had friends that were willing to let me kind of bring my, suitcase, you know, over and sleep at their place for a week. So yeah, that's,

Ben Tregoe: Let's look at the other side of it.

Ben Tregoe: Like any common mistakes or, I mean, obviously the absence of what we discuss can lead to mistakes, but do you see any commonalities or mistakes that CEOs particularly in like the kind of earlier stages

Jack Dreifuss: are making? Yeah, I'd say sort of two things. I mean, I'd say at an individual level the mistakes can be believing your own bullshit kind of too strongly.

Jack Dreifuss: Where you may have a sort of, and I made this mistake actually when I was the CEO and founder of my last company, where I was setting up for a big mission statement around personalized medicine. And yeah, I had a lot of gaps in my understanding of how that actually got accomplished. And, so I hired a lot of really smart scientists and engineers to kind of help me march towards that vision.

Jack Dreifuss: But I didn't realize as the CEO and as a very strong voice and opinion, I think I was shutting off a lot of other perspectives that should read the surface. So sometimes it's hard to sort of see beneath the surface what somebody's really thinking versus what they're expressing. Especially because me, I'm an extrovert, so I'm always constantly willing to share and be open.

Jack Dreifuss: I'm, a fairly well person too. Not everybody's like that. Some, sometimes people take a little while to kind of warm up and, share what they really think. Yeah. And so I think I treated a lot of the world the same and, so I'm mapping my own mistakes onto people, which. Recognizing your own power and your own influence.

Jack Dreifuss: Yeah. That you're, recognizing where sometimes you may be blocking unintentionally information that should be coming. Like if you're a good general, you want your soldiers on the front line or your, commanders in the middle of the front to, share if there's, you know, potential issues going on.

Jack Dreifuss: Right. That, If they're too intimidated or unsure of, how to kind of communicate that cuz for whatever reason, then you're, unintentionally blocking insights and perspective that I think I blocked early on in, in my sort of CEO Foundership role. And, I think I, I believed my own, like I said, BS to too strongly.

Jack Dreifuss: And so I was unable to, I went from kind of pitching the, venture funded story and raised a couple million dollars. Needing to level head myself a bit in terms of how to actually march towards this big, lofty kind of, yeah. Agreement. And what I'll say second to that, to wrap the point up, is I think sometimes there's a perverse incentive between what VCs want to hear from founders when they raise versus the practicality of getting there.

Jack Dreifuss: Right? VCs are swinging for the a hundred x or bus. But they won't admit that they're okay with the five x . I mean, they're fun. If you think about it, is underwriting to a you know, call a four to six, I think is the standard kind of returns. And then like, if you kind of Google like six to eight or eight to 10, you're killing it.

Jack Dreifuss: Four to six is great, you know, two to three is alright. But if. Another way to get to four to six is if you bet on a bunch of companies that provided four to six x returns, four to six, right. Whereas I think a lot of times the investor approaches, I'm gonna have 90 losers and Right. [00:25:00] A hundred x that's gonna return the whole thing.

Jack Dreifuss: So I think that oftentimes for me, I took it very, emotionally and seriously that like if I wasn't getting early traction and product market fit to get. 10 billion outcome. Yeah. That I, kind of felt like I was, I had a sort of all or nothing mentality and it didn't allow me to kind of simplify the steps it took.

Jack Dreifuss: You know, I'm sure with you, you probably have so many things that you wanna build that's probably multiple years out from having the resource time. To be able to do that. And so it's like prioritization is, I guess the the simple way of looking at it. How do you, go from pitching a big vision to investors and getting funded to go towards that big vision to saying, All right what's the 30 day plan?

Jack Dreifuss: What's the 90 day plan? Yeah. Get us there.

Ben Tregoe: Going back to, what you were saying about not shutting yourself off from feedback. You know, it's incredibly, and I think one time, one thing that first time founders or you know, CEOs don't necessarily realize how loud their voice is in the room. You know, it's maybe not intentional.

Ben Tregoe: So how do you correct for that? Cause just being like, Hey guys, tell me anything, you know, isn't gonna get the trick done. Like, have you seen any good techniques for really eliciting the truth? The team.

Jack Dreifuss: Yeah. I think having structured one on ones that incorporate a very sincere reciprocal feedback session of the good and the bad.

Jack Dreifuss: So what would be

Bainbridge_EP12_JackDreifuss_2022_V2: an

Ben Tregoe: example of that? What would be aru good structured one on one?

Jack Dreifuss: I think having a, having one where there is dedicated, So, you know I'm, sure, I imagine if you don't, you probably plan to have, you know, some sort of one on ones. The people manage and, then maybe, you know, your co-founder Yeah.

Jack Dreifuss: Or you have one co-founder or you two co-founders.

Ben Tregoe: One,

Jack Dreifuss: Yeah. Yeah. So I think having a dedicated period of time that's consistent so that like somebody knows that there is a consistent period every week. So let's just say, you know, you're managing an inevitable sort of head of sales that you'll hire, Right?

Jack Dreifuss: Right. That you're the head of sales, and then eventually you're gonna hand that over. Some senior person, if that senior person that you're managing knows there is a 10 minute period every single week and they're one-on-one with you, that they're gonna be able to have a good and bad feedback session of, tell me something that's not going well and tell me something that is going well and that's top of mind.

Jack Dreifuss: And don't overthink it. Just like, what for, you know, I don't like the way that you interrupt me. In meetings or you know, I don't think our product is ready on this front and we're getting a lot of pushback or I have an issue working with so and so. Yeah, side the good, right. You know, it's always good to have boths, so it's, you know, I sometimes you can call it a shit sandwich where you have kind of two pieces of bread that taste good and then one, you know, just wrap whatever that's between there.

Jack Dreifuss: So I think. I think that having that dedicated time, Also then prevents chaos. Because otherwise if somebody, it prevents two things, it prevents chaos where it's like arbitrarily, you're like, Hey, I need to talk to you, or Right. Whatever. And then it's too late. Yeah. And then it's too late. Or it's in the middle.

Jack Dreifuss: It's in the middle of a flow like that something else is going on yourself and some other problem. And yeah, like, Hey, I don't like, I don't like the way you look at me, or, you know, whatever, . But if that 10 minute period is is, sort of is, you know, very sacred time that you, that I know.

Jack Dreifuss: If I'm your head of sales and I know that I have this 10 minute period and my one-on-one with you every week, that I can give this feedback. I think that it, it starts to kind of create some, structure around the chaos, but also gives a very dedicated sort of, you know, confessional so to speak, to be able to Right.

Jack Dreifuss: Get it off somebody's chest. Cuz the other issue that also happens, One, you have maybe the vocal person who will just give you the feedback arbitrarily. And then we don't want that. Cause we don't want just arbitrary emotional, you know, perspectives kind of flying while we're in line of duty. But if, but, and then the, so that's one.

Jack Dreifuss: And then the introvert might not be ever willing to share it because they're just kind of keeping it down inside. They don't know if finding the right time to do that is so you're preventing the extrovert from just like spewing. Right. And then giving them that dedicated space, and then you're enabling the introvert to know that is a safe space to communicate the, issue that they're having that you want to know.

Jack Dreifuss: Right. You don't want them to bury it down inside. Yeah. So I think having that dedicated sacred time in a one-on-one setting where, it's safe to kind of speak your mind very clearly. And then I think the [00:30:00] other thing I'll sort of finalize this with is I think it's important for you as the leader or the manager or whomever is conducting the one on.

Jack Dreifuss: That's receiving that information to actually offer the exact same thing back to that person so that it also kind of, you know, it normalizes it, right? It's not like this, like, you know, this person looking up to you and sharing it, but it's like you guys are both sharing the same set of feedback, good and bad.

Jack Dreifuss: And so I, yeah, that's, I think that's a good way.

Ben Tregoe: Is that the key to a good structured one on one or what? Are there any other.

Jack Dreifuss: Yeah, I mean I think that the one on one two is an opportunity to go through critical KPIs. So there's obviously just the tactical stuff. Like I've had early in my career, I had one-on-ones with the CEO that at one of my first jobs where I was leading revenue, where it was just like, What's up?

Jack Dreifuss: It was just kind of a time to talk and, you know that, I naturally took the reins of that cause I'm a pretty vocal person to, kind of speak my mind on things. It was a bit arbitrary and, I felt like oftentimes we'd walk away and there wouldn't be actionable steps. Yeah. So I, think another thing is, that whatever you fill that time with, make sure there's some sort of a progression so that, you know, the next episode in the TV series has a progressive plot.

Jack Dreifuss: Yeah. So that your next one on one might be there might be a specific actual step. And then what you can do is, in that one-on-one review. The one on one from the week prior and sort of see what was our actual steps, what were some of the concerns, what were the positives? See how they, Yeah.

Jack Dreifuss: It's always good to have a, a basis of comparison. So, you know, oftentimes it can just be a, way to kind of track what's going on KPI wise, what, you know, if it's sales, you know, how is our sales for the week within whatever measurements you kind of wanna Yeah. Put in there. The actual, the feedback piece and then making sure you kind of cover.

Jack Dreifuss: A reflection period of what was the, you know, prior weeks one on

Ben Tregoe: one? Yeah. Wow. That's super. That's great. Yeah, it's like, that's like a, You just wrote a book right there.

Jack Dreifuss: I know. It's funny. I gotta make sure Patty actually heard this so we can incorporate that. I think the, this the inpatient consulting one on ones.

Jack Dreifuss: Yeah.

Ben Tregoe: Yeah. Then you said a second thing was lack of prioritization. Any tips on

Jack Dreifuss: prioritization? Yeah, that's that's a certainly a delicate dance, right? I mean, I think on the one hand, you, as the if I'm speaking to kind of a leader, right, and the CEO or founder or co-founder, it's like that's a little bit of you know it's, part parts, part art, part science, right?

Jack Dreifuss: So like, some of it's gonna be, you know, using as much data as you can to, prioritize. And then some of it's just intuition. I mean, part of the, my betting as an impatient investor, Is, I'm betting on people's ability to have that sort of gut intuition and that sort of ability to kind of traverse the, gorilla warfare that is kind of building an early stage startup.

Jack Dreifuss: Yeah. Especially through the period of getting product market fit, where there isn't an exact clear set of instructions. You know, I, I kind of described that the earliest days of building a startup is, you know, maybe you've driven truck, a semi truck before. But now all of a sudden, you know, or maybe you were in the, maybe you didn't even drive it.

Jack Dreifuss: Maybe you were like in the front seat or you were in the back of the truck or whatever, but now all of a sudden you're driving that pickup truck with a blindfold on and the truck is on, is driving on a frozen lake and you gotta get off that lake onto the road. So, you know, I think that a lot of it is kind of a gut feel.

Jack Dreifuss: You know, you have a sense of how the truck move. You have a sense of how ice breaks. So there's a sort of like, you know, where you speed up, where you slow down. And you know, I think that prioritization is just a constantly evolving thing, which is why I like the lean startup methodology of kind of, don't overthink it too much.

Jack Dreifuss: Don't, create too much of a structure and an elaborate sort of plan, but test as often as possible have a basis of comparison so that you can ab test and say, Hey, if you're prioritizing while you're prioritizing against other things, so you're gonna naturally need to make trade offs. Yeah.

Jack Dreifuss: And just you'll, continuously the same way. Like, you know, I remember my first car when I was 16 was a manual car. I wanted to get a stick shift. Yeah, I still remember those early days of like having to like look as I did at RPMs and then, you know, and eventually it just kind of became a thing where you just, yeah, you could hear the engine and you, knew the timing and it just kind of works, right?

Jack Dreifuss: And then you can get a faster car next. And so I think it's just kind of a, in the beginning days you are really [00:35:00] critically thinking about it and comparing data. Trying to do as best you can, but don't let too much time pass before you make a decision. And then just know that how, whatever is the outcome of that decision, good or bad, it'll be informative so that the next time you have to prioritize, you're gonna be even more smart.

Jack Dreifuss: You're gonna be smarter about how to do that prioritization. So constantly testing appreciating that trade offs are inevitable, and then eventually kind of build up that intuition that most founders should have innately. Yeah you, get into harmony with it. You get closer to it. The more decisions you make, the more time you make.

Jack Dreifuss: I mean, the last thing I'll say is I think a lot of times Silicon Valley kind of really, championed the kind of young Stanford, Harvard dropout to be the founder. And that can be certainly cool because that person's obviously gifted young and confident enough with an ego. Allows them to be able to believe they can make decisions for within the context of something they've never made a decision on before

Jack Dreifuss: And I think that can be good to an extent because in a way it creates, there's a certain level of fearlessness and clearly the person is gifted naturally. But I can tell you that, you know, me now, being 31 years old, I feel like I'm actually one years old in terms of my understanding of how the world works in both business and frankly the social world where I finally feel like I, I've gotten to the other side of a, lot of naivete.

Jack Dreifuss: A lot of anxiety I had around making very blind decisions. Yeah. So I I'm a, I'm, I've been humbled by time many times in, my life. Yeah. That's, And so I think I I have an, appreciation for experience, but I still wanna punch above my weight class constantly. I mean, that's where the fun exists.

Jack Dreifuss: Right. You know? Right. It's, fun to get in the ring in the weight class that you haven't fought in before. So I'm constantly doing that, but I feel like. I've been in the ring enough times, even maybe I haven't taken as heavy of a punch before, but I've, certainly, I've taken enough punches to know what it looks and feels like and sounds like.

Jack Dreifuss: Yeah.

Ben Tregoe: Oh, I'm gonna switch gears a little. We've, I mean, this has been fascinating, very much personal development, and now I wanna switch to like, kind of the market. So for future listeners, it's October 27th, 2022. Not the easiest. You know, there's certainly a challenging period for a lot of companies, particularly in E-com.

Ben Tregoe: You have this interesting, you know, perspective across your three efforts. What are you seeing in the market?

Jack Dreifuss: Yeah, I mean, I think the classic one, right, is everybody kind of pushing for profitability. I think, you know, and it makes sense, right? When, interest rates were zero, Which they effectively were for 10 plus years.

Jack Dreifuss: You know, money was free, so it was like grow at all costs cuz we're all kind of operating off of a money tree right now. And so in a world where you have 0% interest rates, PE ratios could theoretically be infinity. And so it was okay for companies to lose a lot of money. And so I think the era that sort of created the, especially the millennial D to C, millennial, D to C class, The Allbirds and the, Warby Parkers and the Tom shoes and, the likes.

Jack Dreifuss: think that those, companies came in an era where, one, it was cheaper to market on Facebook, you could throw a dollar in and get $4 out. Now you throw a dollar into Facebook as a brand and, you're doing well if you get a dollar back. Yeah. Assuming that you create retention, you can get profitable in the, you know, second order and third, And that, So that's from the consumer standpoint and that's now creeped into SAS as well, where I think there was an era where money was just gonna continue to flow.

Jack Dreifuss: So growing at all costs to disrupt the incumbent or build something new was certainly supported by the, capitalists is you know, so the operators could take more risks knowing that they could raise money whenever they needed. But now you see all these valuations that kind of came, especially outta last year and the year before that are being slashed dramatically.

Jack Dreifuss: You know, Instacart, carna, a lot of companies going down 70, 80% in valuation, which is a huge drop off. But granted, they were fresh off of going up 80 to a hundred, 200% in short order when you're actually having the progress in the business. So, you know, I think that you used to be able to raise a Series A off of.

Jack Dreifuss: 500 K in Arr, a hundred k in a, in the SaaS world now, it's definitely closer to like three, three to 5 million. And that's because capital's more expensive. And so in a world where that doesn't seem to be changing too much we are definitely moving towards an era where, I mean, even so, I don't know if you saw Shopify's earnings today, right?

Jack Dreifuss: They, had [00:40:00] good earnings. The company was up 18% on the news. But you know, the most notable headline was was a ceo saying, you know we're, we are gonna return to profitability. That is gonna be our plan going forward. So I think that sort of is, a big part of it. And you know, I've got some other theories about what, the sort of future state of the next generation of.

Jack Dreifuss: Sort of SAS 2.5, right? Not to be confused with Web three is looking like, you know, you guys are certainly in that class of, next generation of companies. So I think profitability is, definitely one where capital is more expensive. I think you're gonna see a world where people want to be able to do more with less.

Jack Dreifuss: I think that the world of best of breed. Was, I think last, class, last generation sort of mode of, operation and innovation. But I think you're gonna see a lot more consolidation, A lot of m and a. What do you

Ben Tregoe: by best of breed

Jack Dreifuss: in this? Yeah, so best of breed, right? Used to be that in, the sort of methodology of if you're, acquire, you're procuring implementing software.

Jack Dreifuss: If you run a company, best of breed. Taking a given sort of tool or product or platform or rather, instead of getting a platform that does everything you, take, it's the hub and spoke. You buy the spokes that do got it individual thing. You get the best payroll system, you get the best project management system, you get the best customer support system.

Jack Dreifuss: So you're buying basically individual as opposed to buying one platform that does everything. Got it. Yeah. So I, think that the era kind of going forward is that you're gonna expect more for less outta your platforms. Right. Such that it'll be able to provide, you know what, maybe five years ago you could get away with just doing one small thing really well and there'll still be room for that and that, but that needs to be very innovative, I think.

Jack Dreifuss: Yeah. The period of kind of innovation was, you took a lot of offline. Adams, you know, bits versus in the world of Bits versus Adams, you had a lot services, Adams based sort of business businesses that existed that were then digitized. Yeah. In tech and SaaS kind of being two of the bigger areas. And now I think you're kind of moving where that worked.

Jack Dreifuss: And there's a unicorn payroll company. There's a, you know there's a unicorn cap table management software platform that, you know, again, previously was just a crum. You know, services business with a website. And so I think now you're gonna see a lot of, you're gonna need to see a lot of consolidation, where you're gonna see the big players needing to stay really relevant by acquiring smaller products, best of breed products to kind of bolster their platform offering.

Jack Dreifuss: And then I think you're gonna see a lot of the new ages new age companies doing a lot more out of the. So I'm an investor in a company called Party Round that just rebranded to Capital. And you know, they're gonna be consolidating several different financial tools into one unified platform.

Jack Dreifuss: So I think we're kind of in the like post API world where there's a lot of as service backend services. Yeah. Allow you to build a variety of front end services with your own user experience. Consolidate it, organize it. . And so I think you're gonna see a lot of next generation platforms that do a lot more, a lot faster.

Jack Dreifuss: And one consolidation, consolidated experience, and then anybody that is kind of a best of breed, sort of individual, sort of like focused sort of product is gonna require a hell of a lot of innovation to be relevant. It's gonna really be able to be an innovation on the product side, not just on the, you know, the business or not on the The model of like, you know, SAS just kind of offered a subscription to spa based software.

Jack Dreifuss: So that's kinda a bit of a thesis. Do you think that

Ben Tregoe: it, do you think the, sort of broader platforms that you're describing is, does the customer, is the customer making the choice that like, well it might not be great at a lot of it or everything, but it's good enough, but it certainly is the right.

Ben Tregoe: or are you saying that like No, these platforms are gonna be great at everything. There's no compromise

Bainbridge_EP12_JackDreifuss_2022_V2: in

Jack Dreifuss: choosing them? That's a really good question. I think I would say, I'd say that if the provider right, the product or the service is doing a good job, then they're, able to demonstrate [00:45:00] their ROI very clearly.

Jack Dreifuss: Such that the buyer knows exactly what they're getting and why it's valuable. And so I think demonstrating roi, I think ROI was a fairly loose fitting thing for a while because you could kind of just like make it like, eh, this is cheaper than what you had before. And yeah, it seems a little easier to use and you know, it kind of just like back of the napkin and be like, All right, let's do that.

Jack Dreifuss: Like, and Right. Again, everything's just getting tighter. Right. And that, I think you, I made the point earlier about how, you know, you used to be able to throw a dollar. Into the Facebook marketing machine and, get several dollars back very easily without needing to run a very sophisticated ab tested right paid media campaign.

Jack Dreifuss: But now you need to be real, like at the, on the agency front you know, the agency's called Media Wire. And I partnered with a guy there who came up through the infomercial world. where he understood direct response marketing. So, so, so, so clearly cuz and it was a lot of baby testing, really small things.

Jack Dreifuss: And so he's always thought about approaching this stuff with, marketing really profitably, but also very, with a very data intensive approach. Yeah. You know, and so I think that getting smart about data and really tightening up that presentation. The customer and the provider are really in sync about return on investment.

Jack Dreifuss: Yeah, and kind of, we've been talking about kind of for a long time, you know data, but it seems like people are still fairly rudimentary in terms of how they present data , and so I think that obviously bodes well for a business like you guys. You had some maybe CFO who was fractionalized, kind of helping a 30 million D TOC business kind of get along and update their spreadsheets once.

Jack Dreifuss: We mean that's gotta be real time. A brand can't afford to not know exactly what their sg and a costs and you know, cost of good sold are and relative to their marketing spend, you know, they need to be able to make time data informed decisions. And so I think. That both presentation as a provider, you know, being you guys, Bainbridge and then that consumer, right, in your case, a consumer brand or anywhere in the sort of provider and, customer side.

Jack Dreifuss: That fair perception around ROI is gonna be hypercritical.

Ben Tregoe: Yeah. Interesting. Jack, we have eight minutes, so there's a lot to go through. Cuz I want to make sure the listeners. Know what are, if they're a good fit for you. So let's start with inpatient vc. What are the types of deals you are looking for and, you know would seek, out?

Jack Dreifuss: Yeah, no, I appreciate that. So yeah, my, my investment sort of career was very organically. I like to think of myself kind of as a founder first, and so I, I approach kind of my investing similar to how I think about starting a business, which. Am I excited to work on it and in my excitement is driven first and foremost through people.

Jack Dreifuss: I'm not naive to say that I'm just gonna invest in somebody because I like the person, but it's much more of like an intuitive feel that like I have a good gut understanding of what I believe a good founder's kind of got the right sort of genetic makeup in terms of how they talk, or the way they think, the questions they ask, the curiosity they have, even their sense of humor.

Jack Dreifuss: I, I've kind of, I. Say this somewhat whimsically, but I really believe that for me, from a culture building standpoint and from who I like to work with, I think a good sense of humor. You know I've come off offensive to the to, to, the wrong person when that, at all my, intentions were not to be offensive in the least bit.

Jack Dreifuss: And so I think for me, good sense of humor is a pretty high signal for, apt. I think aptitude is a pretty dynamic thing. And so it's everything from curiosity to not taking anything too seriously but of course taking things very seriously. . So, you know, I think that for me it's a very people first.

Jack Dreifuss: I get excited by critical thinkers. Dynamic thinkers, people that see the world in a particular way that I can align with. And then like, you know, I like to collabo. I'm a, I like to be a thought partner. I like to break open doors, so for me, I tend to invest in stuff where I have some sort of a leg up.

Jack Dreifuss: Certainly in the commerce tech space, it was, you know, unfortunately I missed your round at the talent, but I, you guys would be a great qualification. The type of business I invest in you. Oh, thanks. In a problem area that it makes a lot of sense, especially in today's world of needing to really get your your, roi, your fp and a costs down pat.

Jack Dreifuss: Have it be really accessible and, accurate. So certainly, you know, I look at the kind of SAS 2.5 [00:50:00] world as folks that are innovating in traditional software as a service that tend to like FinTech as well, where yeah, they're either consolidating a lot of different spokes into one unified platform.

Jack Dreifuss: That's why I mentioned I like that company Capital X, Y, Z, formerly party round, or they're consolidating, you know, payroll. Banking cap table fundraising into one unified platform. Wow. So they're not there yet, but they're, kind of moving towards that. Yeah. They're taking on a lot of people.

Jack Dreifuss: There's a lot, of people. They're taking on, a lot of people for sure, but they're not, But they're, taking on a lot of people in the sense that they're not trying to really migrate people off of, you know, ramp bras, Mercury. Yeah. And, you know, rippling and and Carta, they're, they look at that as like, all right, those guys have built huge business.

Jack Dreifuss: There are huge businesses that are built off of those platforms. But they're looking at the next generation of startups. Right.

Ben Tregoe: Haven't made those choices

Jack Dreifuss: yet. Exactly. Yeah. I certainly do look at some web three stuff, but I'm hyper critical. I am not just in it to, invest in a token that can get liquid in 18.

Jack Dreifuss: Oh, come on. They don't, they never go down. Seemingly. Although now they finally have. Right. So it's like, I think a lot of, I, I was kind of losing my mind last year looking at crypto stuff. I mean, I definitely have, made a number of web three investments. I'm looking at these investments as, you know, five to 10 year bets.

Jack Dreifuss: Yeah. Not, one to two year or even less than that kind of return on my invest. So I'm certainly a long, you know, even though my fund is called Impatient Ventures, it's kind of, you know, intended ironically in that like the world is very impatient and wants everything now, right. The rest stuff takes time.

Jack Dreifuss: So certainly looking at just the next generation of like, what is the best in class products. And that's driven, I think, in a combination through, you know, real product innovation on the sort of SaaS side. Where they're actually doing, they're, they have an offering that you just literally couldn't do before.

Jack Dreifuss: Really critical thinkers around distribution so that they have the ability to create really meaningful, unfair advantages from a Product, excuse me, from a product distribution standpoint. So all things sort of sales. Yeah. And then for me the, reason I honestly spun up inpatient consulting alongside inpatient a ventures wasn't to really just sell my whole portfolio my consulting business.

Jack Dreifuss: But it was, I just had so many of my. Investments in my portfolio founders wanting more of my time. Yeah. Like, right. I gotta make sense of this, you know, And I and, so I gotta kind of start to charge for over and above time that I'm spending kind of working on this. Yeah, that's interesting. On this.

Jack Dreifuss: And so it was really, I actually, I didn't even think about that. I just eventually had some of my portfolio companies sort of say, Can we pay you to come in and, do this? And I was like, I guess I, I've kind of thought this was a separate church and state model and I just had to kind of do as best I could to manage my time, but because I'm making 10 bets, I gotta pay, you know, I gotta pay the bills.

Jack Dreifuss: Los Angeles and cheap here. So it's been, but it's been fun, you know and I enjoy it. And then from a marketing standpoint, I mean, we work with consumer businesses, so it can be digital products or physical products. . You know, we work with some of the leading brands Oats overnight and Black Buffalo and Mad Rabbit some of whom are our clients are soon to be clients at you guys, which is great because, yeah, it's awesome.

Jack Dreifuss: Us as an agency we, tend to also be very focused on being able to create our own internal representation of what profitability looks like. You know, most agencies don't really focus on that. For us, our pricing model is built. How much they spend on marketing. We don't have any retainers. So Nice. You know we, like to work with consumer businesses where we can, like the people we work with, where they trust us, we trust them, and we can integrate really well.

Jack Dreifuss: Yeah. Cause if you don't have that kinda like ability to like the person, then you're never gonna trust the person. Yeah. You're gonna work together and so, you know, you're not gonna like everybody you do business with in your life. But the closer you can get to that, to me, the more fruitful, the more motivated both parties.

Jack Dreifuss: The less you're looking over your shoulder, the more you're willing to indulge mistakes, right? Yeah. Cause things happen. So yeah, I mean, that was a little bit of a mishmash, but, you know still, actively investing. Super excited about it and you know, I think that the next generation of startups are gonna be really interesting.

Jack Dreifuss: I think we're kind of going, we're kind of going through a portal right now into the sort of next generation, so certainly, yeah. I think it's exciting too. Class. Yeah.

Ben Tregoe: Well, Jack, thank you so much. I really appreciate your time. It's a fun for me and yeah,

Jack Dreifuss: thanks.

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