304. IT and Enterprise Tech Investing, The Realities and Myths of PLG, and The Past and Future of NYC Tech (Jonathan Lehr)

Jonathan Lehr of Work-Bench joins Nick to discuss IT and Enterprise Tech Investing, The Realities and Myths of PLG, and The Past and Future of NYC Tech. In this episode we cover:

  • Walk us through your background and path to VC.
  • Tell us a little more about the thesis at Work-Bench. 
  • On your website, you mention you invest in “seed and seed II” startups. What is a seed II?
  • What sort of myths are there around PLG companies?
    • How do you advise startups to price their products?
  • Mark Suster recently Tweetedโ€ฆ  “If you look at our industry, it’s now awash with capital that requires every firm to get very focused on where its edge comes from. If you’re not a bulge-bracket VC, choose your positioning wisely”(stage, sector, geography, founder access) โ€ฆ way too many firms are generic”. What are your thoughts on the financing environment?
  • You’ve been a part of the New York tech ecosystem for about a decade now. How has the tech scene evolved over the past 10 years or so? 
    • There was a dogma for a while that enterprise startups had to be built in Silicon Valley. Why do you think this is a mistaken belief?

Guest Links:

The host of The Full Ratchet is Nick Moran, General Partner of New Stack Ventures, a venture capital firm committed to investing in the exceptions.

To learn more about New Stack Ventures by visiting our Website and LinkedIn and be sure to follow us on Twitter.

Want to keep up to date with The Full Ratchet? Subscribe to our podcast and follow us on LinkedIn and Twitter.

Are you a founder looking for your next investor? Visit our free tool VC-Rank and tell us about your business. We’ll send a list of possible investors right to your email’s InBox!

Transcribed with AI:

Jonathan Lehr joins us today from New York City. Jonathan is co founder and general partner at Work-bench and early stage enterprise tech investor. He has led investments in several unicorns including Cockroach Labs, Dialpad, and Socure amongst others. Jonathan, welcome to the show.
Thanks so much for having me, Nick. It’s a pleasure.
Yeah, it’s good to reconnect. I’ve heard the story before but for the audience, can you walk us through sort of your background and path to VC?
For sure. So at Workbench, we’re hitting our eighth year, actually, which is super exciting. Wow. And beforehand, I actually used to work in it at Morgan Stanley. So our unique stake when we launched was that all of us actually come from corporate IT world. So my co founder, Jessica Lin comes out of Cisco IT, Kelley Mak, her partner comes out of Forrester and I used to work in it at Morgan Stanley. And most people usually associate a big bank with being on the investment banking team being super finance II. But what many people don’t realize is that actually, Wall Street tends to be the earliest and largest adopter of enterprise IT. So I started my career in a really fun group, called the Office of the CIO, and Canada, we were tasked with meeting hundreds of startups a year meaning with all the big name VCs, from the Valley of the Sequoia is the injury since the excels the world to figure out which startups Should we do business with to either generate new revenue, cut costs, drive new efficiencies, and you know, at the time, we had a $4 billion IT budget, so there was a lot of a lot of work to be done. And that’s really where I cut my teeth on enterprise tech. And more important than I would say, even their domain expertise up and down the it stack was this notion of customer empathy, we would get paid on a daily basis by all these Silicon Valley startups, but too many really didn’t understand the process to pitch to sell into into close customers like Wall Street banks, given the regulatory environment, security and architectural requirements. So a lot of that experience is really what we bring to bear workbench.
How does that lead to you? You know, starting a fund, right? Like you’re getting all these insights, you’re interacting with startups. But you know, it’s one thing to see an opportunity, it’s another thing to raise a lot of money. And you know, now you’re on fun three, I think you closed $100 million fund, So congrats on that. But thank you so much, you know, easier said than done.
Yeah, so it wasn’t the I would say traditional path where, you know, for some bigger fund people actually do go banking, and then join a large fund, like an NDA or something like that, or, you know, having a successful founder that joins an Andreessen, there was a lot of luck involved, actually. So by because of my day job, I really was, you know, obsessed with All Things enterprise tech, and I’d actually been trying to break into the VC world. This is back 2012. And, you know, back then a lot of people looked at me and they’re like, you don’t fit a traditional VC pattern. You’re not you know, you’re an IT guy at a big bank. What the hell do you know, and the way that I love to be broke into venture was actually in my nights and weekends outside of Morgan Stanley. I started the New York enterprise tech meetup. And you know, this is back January 2012. I’ve been attending the New York tech meetup, which you know, back in from 2007 onwards used to fill Skirball center down by NYU 800 people, it was one of the original big tech meetups, and you would get an audience of just everyone in New York in the same place. And it was an incredible networking opportunity. The big issue that I saw at that event, though, we’re not issue but opportunity was, if you asked about a business model, you were actually boom, it was all about the tech and the demo. And that was it. You know, in enterprise world, there’s a lot of importance in the business model. The Tech is cool, but it’s like a yes and kind of situation. So seeing the excitement for tech in New York City and really making a bet that given we had all the fortune 500, early adopters, we had the most fortune 500, headquartered out of anywhere in the world back then it was 52. Now it’s in the 60s. And the growing tech ecosystem from the consumer side, right? Google, it opened an office, Twitter, Facebook, and then you had these big tech startups that were starting to spin out technical talent from that Nexus from Etsy. I was like, we got to bring these people together. And you know, my co founder just called it the suits and the hoodies, she came up with that framing. And it really is true, the big corporates and the startups to be able to bring them in a room together. A lot of value could happen out of them and a lot of serendipitous meeting. So starting that enterprise tech meetup running that every single month in 2012, and then in 2013, actually was what led me the opportunity to launch fund one with Jess and that was a $10 million fund and it really was, you know, like many things in life. It was luck. I was in the right place at the right time. And we were able to raise from that got introduced to our anchor LP in the first Fund and the rest is kind of history from there.
Amazing, amazing, Jon Yeah, I remember back in 2014-2015 timeframe, when I was investing time and energy and Twitter and Social and creating some, some content there, I remember people talking about unique models and unique unique paths in the VC. And people would cite you and would cite the enterprise tech meetup in New York City. And how that was kind of a catalyst for workbench shit. You know, it’s it’s quite some time since then. And you guys have had many successes, I think you claim three unicorns in the portfolio. So you know, well done, sir. But tell us a little more, you know, what did we not cover in the thesis on workbench that that we should have done?
So I touched on my background. So Lee using that to lead into what we do at workbench, right, we looked at the VC landscape. And back in 2013, we saw a huge opportunity to bet on New York and to bet on enterprise, but really to do VC differently. So coming from non traditional backgrounds, Jess and I were able to kind of start from first principles, and we realized, in the enterprise, there’s pain points, there’s budget dollars, and there’s priorities. So why are most DC starting at Google’s cafeteria, you know, at the Facebook campus, running around Stanford, looking for kids to fund and then lobbing it over to the big banks, which was the path that most you know, Silicon Valley VCs did, why not flip that model? Why not start with the big corporates in our backyard, right, you have financial services, pharma media, those are all highly represented in New York City. And they’re the early adopters that buy enterprise software. So our model is all predicated on starting with them being thesis driven in our four key areas of investment, that, you know, machine learning AI and all things data. It’s cloud native and dev tools, cybersecurity in the future work. So our whole model and it stays the same over the last eight years is being thesis driven, then finding the best startups solving those challenges. And then quite frankly, just playing matchmaker, helping the corporates with those introductions that are curated, so they’re not being bothered by meeting startups, they’re actually getting value out of it. For the startup or when we’re investing, they have a live product, but they really haven’t started go to market yet. So we’re giving them oxygen, the right intro to the right person curated at exactly the right time. So that’s golden form. For us, we’re not just doing it to be nice people. But what’s really exciting is that as part of diligence, we’re adding value in this competitive VC world. And you know, we’re showing differentiation to the founder, and those corporates give us the back channel feedback. So now we know which ones are actually resonating, which product roadmap is aligned to the enterprise need at scale, which are actually architected in a way to meet a big banks, scalability requirements, who could have the security needs to meet pharmaceutical company’s needs and selling at scale. We package all that together. And then, you know, with the companies that we have conviction, and we’re able to lead three to $6 million investment rounds.
Amazing. So such a value add that the diligence piece, you know, one of it’s been a secret weapon for us at New stack, we invest, you know, across sectors, but if you can get the right customer speaking to this startup, not only the help with your vetting and assess, you know, is there true value here, but you’ve also delivered an incredible potential partner and customer to the startup, which is a huge value add, and I can see how it worked well for your thesis. JOHN, I’m curious, you know, historically, a lot of these banks and even hedge funds and other finance players, startups would get caught in sort of this purgatory of pilots. And, you know, there’s there’s a lot of financial players that love trying out new data and other different types of startups, you know, how have you kind of move past the hobbyist customer into the true enterprise customer?
So I love that question, because you did hit the nail on the head, especially in the financial services realm, it’s not the most friendly to outsiders. So to answer it, it’s really a few, there’s a few components. First of all, in the backend, before we even make an introduction for a startup, whether it’s an existing portfolio company, whether it’s a company where diligence, and we know and we maintain relationships at scale across big banks, big insurance companies, etc. And it’s not just about knowing a CIO or CSO, I always like to use the word tentacles, you need to know 25 different people at a place like a Morgan Stanley or JP Morgan, because the person who owns data infrastructure is different than the person who might own you know, Model Management is different than the person who owns security, etc, etc. And once again, tying it all back to New York through all the events that we host. You know, corporate engagement is a key component but the other big flywheel for us is this community where whether it’s a 1015 person roundtable that’s corporate only, whether it’s our 200 plus person monthly meetup, whether it’s a dinner or something in between, we’re constantly maintaining In this network to keep people warm, as well as growing through warm intro, so step one is understanding which customer let’s let’s stick with the banks, who’s actually doing stuff in this example in the machine learning or the data world, right? A Morgan Stanley may be good at buying early data companies but slower on a cloud, JP Morgan may be active in ML in cloud, but maybe slower in security, right I just to give a few examples. So you really need to understand the nuance of who’s doing what, and who has the pain points. From there, you can then use those relationships to curate the introduction to your startup. But that’s just the beginning. Because as you point out, getting into things like Hey, is there a pilot? Is it paid or not? If there is interest from the pilot? How do you get enough of the business stakeholders involved to actually drive things forward? What happens if they get stuck in procurement? Some banks like to try to throw warrants these days and force your hand? How do you navigate those situations, so all we do day in, day out his enterprise go to market. So we’ve seen this before, we’ve lived this firsthand in our past lives, we have a robust network at the bank to assist our companies, as well as other large corporations. So that’s really where we enjoy our day to day job. And it’s pretty different than traditional VC, because we’re doing the thesis work simultaneously with this portfolio support work, and constantly churning out new insights, as well as new introductions for our companies.
Quickly, you know, you’ve mentioned on the website that workbench invest in seed and seed to startups, you know, what is C two? And once Yeah, it’s,
it’s so funny. So we actually just had our annual meeting with our investors the other day, and we were actually giving a presentation on this because during the last fun, you know, 2017 to 2020, we called it c two, which was a three to $6 million round, usually, a company had raised maybe one to 2 million before, and in the enterprise a series they had ballooned to 15 $20 million. We filled that gap where there was a live product, but you needed to really turbocharge improve that go to market fit element. What’s funny is that same exact round over the just the last 12 months alone, has now become really what’s called a seed round. And it’s the big joke that it’s the same exact thing. So the stage is the same. But given the environment right now and how frothy it is, what was a seed a year ago is now being called off in a pre seed. And I’m curious if you’re seeing that as well. But companies are raising one to two, and it’s called pre seed. And that’s usually what we’re seeing on a safe note, folks aren’t taking a board seat and it’s really to maybe get v1 of that product. We’re we’re then coming in is leading the three to $6 million round with a check that could be three, three and a half million dollars. It is taking a board seat being very actively involved helping with that go to market work, and then teeing them up for that 15 $20 million series A so nomenclature aside, you have that early. You may not have any customers, we’re gonna fit right in there to help you scale.
Got it. And the goals of that round would be product market fit, and some some sort of go to market fit as well. Exactly. Yeah. Yeah. Got it. You know, you wrote some content recently on product led growth, be curious for you to kind of maybe highlight some of the realities and some of the myths around plg and plg. Companies?
Yeah, the biggest. So we actually did a massive summit, we had 90 seed backed founders that were in attendance. And we had two incredible speakers. One was Jean, who leads revenue for the Americas at stripe. And then another one who was a former port co PM, cockroach lab, Diana Shea switch a timescale and actually correlated, so two different ends of the spectrum. And I would say the biggest myth, if you look at the twitterati, and what people are blogging about is that plg bln, doll, full stop, like you’re doing bottoms up, sales is dead, you don’t need any people anymore. And I think a lot of people that might come from the web skill world coming out of a Google or Facebook or Twitter that don’t necessarily have enterprise sales experience, may think that if you build it, they will come. And quite frankly, that’s not the solution. What we really touched on in the summit, and it was great to hear from Jean, even in a place like stripe is it’s Yes, and certainly a lot of the waves these days for many type companies are different touchpoints with your customer before they’re actually signing up, right? Whether it’s an open source product, whether it’s a freemium, whether they’re downloading something, log into a SAS app, and managing all those touch points. The key though, is understanding now in this new world who’s doing a credit card swipe, but where do you actually get an A involved who could actually lead to a true team sale who could then land and expand from there to go maybe organization wide. And to tie in another event that we had, we actually had Jeff Lawson, the CEO and founder of Twilio speak at our enterprise tech meetup earlier in the year. And one of the most interesting nuggets for the audience was that he actually said he wished that he hired enterprise sales team sooner. Clearly he’s been incredibly successful. Twilio has been a phenomenal company. But even he was saying that he waited too close to the hype. To and they could have even been bigger in hindsight. So that’s probably the biggest thing I would say. And then you know, feel free to any listeners check out our blog because we got pretty tactical we did a session on specifically the product side, this go to market summit was on more of the, the growth side and sell side. And that’s something that we’ve really been spending time on in the last year or so
How do you advise startups when pricing their product?
So the the TLDR is that there’s no one size fits all. It’s something that takes so much trial and error, so much really hypotheses and then measurement and tweaking. I mean, we have some companies that are going in pretty top down for million dollar plus a CVS, we have some that are going in with API pay as you go models, we have some, you know, more traditional SAS based companies with everything in between thinking about things like consumption pricing now, or fair seat pricing, which I think was slack that pioneered a few years ago. It’s something that we have a lot of folks that as our companies mature, we really tap into them to keep mentoring our earlier stage companies because it’s continuing to evolve. And we just want to make sure that we’re trying and measuring the right things so we can double down on the right strategy. But there really is no one size fits all, I would argue
Is there an ACV that’s too small? That gives you a concern?
For our model 100%. We are not a firm that can really focus on those $10 a month or even like $100 a month $1,000 CDs, we’re not going to flex our muscle there. Where we really love to engage is when a company could have 50k starter acbs but growing into six figure like 800k plus starters with expansion potential beyond that. So that’s what I would say our sweet spot is on the the mid market lower end. And then we have some companies that again, start at 300 500k arr. That can grow to multimillion dollar accounts.
Yeah, Jon, there’s, you know, lots of ink spilled recently about how the industry is kind of awash in capital, Mark Suster just tweeted about this. He said if you look at our industry, it’s now a wash with capital that requires every firm to get very focused on where its edge comes from. If you’re not a bulge bracket VC choose your positioning wisely. Stage, sector, geo, founder access. There are way too many firms that are generic. What are your thoughts on sort of the state of the industry, the flood of new capital, and what that means for for investors.
So I found his piece super onpoint he’s way more articulate than me so I’m glad he wrote it cuz I’ve never been a nice summary of the of the landscape. But you know, when you have the traditional firms, the sequoias and reasons that keep doing great at what they do and getting bigger. That’s one element. When you read in the press about Tiger as well as insight ventures out of New York City going earlier in earlier. Insight, for example, is more traditionally known as akin to a PE fund. But now you see him super active in series B’s and series A’s. And then you look at tiger, you know, in q2, they were doing 1.3 deals a day. I don’t know the latest q3 stats, but if you’re a traditional generalist fund in the valley that was doing series A, I think you’re in big trouble because you just cannot diligent and you cannot act in time. Now the other piece of that equation is everyone’s launching a seed fund, right? You have index and teresian, XL Sequoia all have multi 100. I mean, Greylock just announced a 500 Raloxifene. So, you know, I think if you’re in Silicon Valley, in particular in your generalist Seed Fund, once again, when a firm can write a $5 million option call and you know, tout all this good stuff that they’re going to help you with as well as the brand association that could give people pause. Where I agree with Mark is if you’re someone like you, someone like us that really has a bread and butter focus, right? Like we are enterprise software experts, we’re going to add diligence people with our network, we’re going to out support people with the same network as well as our community, which gives us tremendous leverage. So we’re gonna get insights and at quicker you also pair that with really the focus for us being New York City that 75% of the portfolio, right? I think we have enough of an edge here in our backyard. And then we will opportunistically look in Seattle and the valley in Boston, but we really know what we are. And arguably more importantly, we know what we’re not we’re not FOMO investors right? We’re the anti FOMO VC we don’t we do in a fund 1718 deals So think about that six a year. Pacing wise we need to have pretty high conviction in what we do so what Justin I always say to the team and to our investors is you don’t have to do every great deal but we every deal that we do at workbench has to be great and it has to meet what we’re seeing is Market pain point and incredible founder and the ownership requirements, we have the dollars that we need to put to work because you know, there is that financial element as well. And I think in this market, too many firms are changing their behavior. And you have people tweeting about valuations not meaning anything anymore, and just get into hot companies and throw small checks, and then you’ll get bigger checks, but everyone’s competing more than ever across stages. So I really think it is my agree with Mark, I think it is important to know what your bread and butter is and be able to say no, to everything else.
I mean, it’s it’s clear that the Bay Area is is way overheated. I mean, I talked to fund managers on a daily basis that are a bit exasperated by the whole thing. You know, what have you seen in New York is it also becoming much more competitive to win these seed or seed two deals, as you call them?
So what I would say is in New York, we have a pretty vibrant seed b2b and broader enterprise ecosystem. And I wouldn’t say that it’s too awash with non local capital yet, so we did an analysis actually Priyanka on our team, our senior analysts looked over the last 18 months of New York specific funding data. At the seed stage 50% of deals are led by a New York City firm, it’s really at the series A where you see the outsiders come in, because only 28% at the series A are actually led by local firms, you get a lot of cash coming in specifically from the valley. So you know that I think competition is always healthy, we have a lot of friendly firms that we work with here. I think at the pre seed stage, it’s heated up more than ever, because you do have people realizing that the broader b2b market is, is is a pretty frothy one, and it’s a good place to play. But again, putting nomenclature aside that first check, you have a lot of generalists and some b2b funds going after we’re we’re really focusing at that live product stage, once they’ve again raised maybe one or one and a half or two, that’s where we can come in. And fortunately, there’s less competition there. And people know what they need, right? If they have sights on that massive series, a from a Silicon Valley fund, they know that they need to have go to market working and eight years of community building content and brand here really helps. And the other piece that’s super exciting, is eight years into the cycle. We try every six months ago, we published a New York City enterprise funding report. So you know, the CB insights one came out that’s more generalist, but we do it with a specific view into enterprise software. And I think was something like 6.7 billion was raised in the first half of 2021. That was a massive step up, it was like 146% growth, and I’m the exact size of them, it’s only like that versus 2020, which was massive step up versus the prior year, right. So we’re at really a maturity where it’s escape velocity now in New York, you had Mongo that went public those first one then data dog, and now you’ve got a ton of other companies and they are starting to spin out the next generation of found. So that’s the most exciting part for us. We’ve been hosting right this New York enterprise tech meetup January is going to be 10 years. Some of those companies like data dog that presented in 2013, and have gone public now their VP level execs not yet, but like they’ll be starting companies, right? We we just back to stealth company that left MongoDB we’re looking at companies with exact from right, namely, he’s in digital oceans and breezes of the world. And to have that branch in New York City. And that relationship with the founders from the VP level dinners that we’ve been hosting for eight years from the enterprise tech meetup that they’ve been coming to for years from the playbook lunches that many of them have spoken at. That whole flywheel that’s been very new york centric, has really reached that inflection point. And it’s really an exciting time to be able to deploy capital into It’s amazing.
So is it about what three to four deals per partner per year? Is that right?
So I would add per year basis, we’re doing about six. So it’s about two deals per partner across me, Jess, and Cody, got it got as well take it, we do 18 in a fund. So it’s pretty concentrated.
And then while we’re on New York, just any other thoughts on that ecosystem, kind of how it’s matured, and sort of where you’re at are the 10 years or so that you’ve seen in progress?
Yeah, so one fun data point I like to share is that in 2021, UI path raised a single round, call it like 575, or something like that million, which was greater than all of the funding raised across all starts in 2014 when we started capturing the data. I mean, that stat just blows my mind. So there has been what’s really exciting is in the early days, you know, you had seed activity starting series activity starting, but now tracking this data almost last seven years, have some nice growth as well. So you had 22 rounds, over $100 million in the first six months of the year when we publish that report. I can’t wait till we do the back half, you know, early January analyzing July to December, I’m sure that number is going to be even more, we had four so IPOs earlier this year, that used to be a knock on New York City, right, not enough exits for the first six months of the year alone, right. So we have all the ingredients, we have the exits, we have the late stage of 18, unicorns and those continue to exit, we developed this our category called the next card, that’s a company that has raised over 100 million or is valued at over 500. We have something like 26 of those. So as you think about the unicorns, the next card all the late stage funding and the continued early stage financing activity. This is I mean, we’re forgetting comparisons to the valley or anywhere else, we have an amazing, like healthy ecosystem that just keeps maturing, keep cycling in the next generation of founders, and we want to engage with all of them.
Yeah, it’s funny, I think I shared this that recently, but I was I was running some numbers for our annual event. And I realized that there’s more unicorns in the Midwest now than there were unicorns in the valley when I started the podcast and in 2014, or not in the valley, but in the Bay Area at large. And so I guess unicorns are are no longer the goal. Everyone’s looking for the decades. Exactly. I’ll take the unicorn.
You got to start somewhere, right?
Yeah, yeah. Jonathan, what are some of the biggest missteps that you see enterprise focus startups and or their founders making?
So it gets back to what I was saying earlier, which is if you build it, they will come. I think there’s way too big a focus on product at the expense of sales. It’s clearly in today’s world you need in order to compete, you know, a very modern well designed product, no one’s going to put up with like an old SAP kind of login, right and dashboard. But with that is your starting point. I think people then go too far, because they may come from the web scale world. And it’s what they’re comfortable with. It’s where they know they can tweak from 98% to 99. But not have the empathy and awareness to realize we need to get in front of customers, we need to understand if what we’re building is what they need, we need to understand when we should be thinking about sock two type two compliance, the least sexy thing you could talk about, but it holds back a lot of companies from scaling their sales organization, when you need to have that in place to sell the certain type customers. And even some of the large tech companies these days that have grown in New York City, as they become now customers to the earlier Garda startups, that next generation, even they have those requirements in place because they’ve either recently gone public or going to and they need their vendors to be in a good place. So that kind of nitty gritty is where we love spending time with companies, because when a founder is open minded, it can be a very collaborative relationship. I’ll be open though a lot of times, co founders in the valley, just think, why do I need this or I can get by without it. And you know, sure, some do. But plan, you have missteps. And that’s a very big cultural difference that we see in founders in New York City, they try to have big visions, and they want to take over market, but they also do understand the blocking and tackling on the sales side that is required. And again, that could be a plg motion, it could be a middle out motion, it can be top down, but strategizing, how to approach that sales, motion, how to hire around it, and what the building blocks are needed. That’s that’s a key element.
Is there a standard background or profile of most of the startup founders that you fund? You know, are they coming from certain functions? Or are they coming from finance for instance?
Yeah, so we we never look at traditional, you know, like, people like to rail and Silicon Valley VCs Did you go to Stanford to do work to go like, we don’t have any archetypes like that, when we do look into a theme. We love a good archetype for us is like if you’ve been an operator building there, so to give three examples, catalyst software is modern Customer Success software competes with gainsight. It’s led by a true who was the VP of customer success at digitalocean saw the pain firsthand built a better solution. fire hydrant building site reliability, really incident management software, he did this role at namely, beforehand, so he knows the pain point and he’s more authentic. When he talks about it, then, you know, some random other leader that hadn’t lived it. And then the last one is, we have a company advisor trust and Paul and Russ come from the security world. Paul was a CSO before at ASAP and a few other companies and the way he’s able to talk, and especially in a world in security, where they sell a lot of Fudd. He’s able to just talk, real talk, he gets the pain point he lived it, he was very commercially focused as a CSO. And their third party risk software is tuned so that it has all these really interesting automation capabilities to help scaling companies with third party risk management. So we love that profile of if you’ve done it and now you’re building it but you know, we have plenty of other companies where the founder had the idea and just got working on it as well.
Got it. Yeah, I love that the operators that have actually experienced the pain often become great founders. I think we’ve noticed here in Chicago, you know, the finance community, you come from finance, of course, Morgan Stanley, but a lot of the finance professionals, particularly, you know, some of the best and brightest in Chicago are in the trading community. And for them to leave behind that compensation to do a startup. It’s just, it’s a non starter, no pun intended. And so, you know, I’m always curious if founders are coming from the finance community in New York, because it’s just, you know, too much, too much opportunity cost lost, you know, for a lot of folks, at least here.
Yeah, I mean, we sometimes on founders, you know, have that much conviction around an idea, or may have that unique insight coming out of finance, I mean, look, of course, a lot of gone into the crypto world, which we don’t spend really as much time in. But we’ve seen people do stuff in the data world or in the cloud world, because they did have unique insight at scale from a big bank, it is less common, I would say, got,
Alright, john, this question is called three data points. So I’m going to give you a hypothetical situation with a startup. And you can ask three questions for three specific data points, let’s say you’re approached to invest in a seed stage, enterprise SaaS startup company is based in New York, they have 200k of arr. They’re growing 20% month over month. Again, the catches, you can only ask three questions for three specific data points in order to make your investment decision, what three questions to ask.
So the first I would ask is, what do you do? Right, and the rationale, I don’t know if I’m allowed to go into the rationale right now. But the rationale of it is, you know, some sectors, like maybe an HR space, it’s a lot easier to get that earlier revenue, and then something like cloud infrastructure, which is a lot harder. So not all revenue is created equal. So that’s the first one, what do you do? Number two is walk me through the split of your customers. So is it you have like two at 100k? Do you have five at 40? Do you have like 100? At two. So getting back to our earlier conversation, the type of revenue in the size ACD contracts is important. And then for the third, I’d say what’s the what’s the broader vision that you’re pursuing? Right? And usually that first product is a wedge in but what’s the ultimate big idea that you have? Okay,
And what if they are cloud infrastructure, they have two customers at 100k ARR each, and the vision is conquer the world?
So what I would say is, for many VCs in this environment, they’ll say, hey, sign me up, here’s a blank term sheet for us, because we do things again, inverted, we usually will have a view into that landscape already. So where we would then pester them is like, How are you different than x and y and understanding what the sales motion I mean, we love digging into how they think the sales machine has been and have like an intellectual discussion about that and push back on some of their potential assumptions. You know, what the team structure is going to be how they look to scale, and a lot of other stuff on that front. We, we dig in very efficiently. But we have a lot of areas that we’d like to cover.
Jonathan, if we can feature anyone on the show? Who do you think we should interview and what topic would you like to hear them speak about?
Yeah, so one of the people that has been so helpful as we’ve scaled workbench, both as a firm but also like, just in terms of mentorship for me in chess, is Sunil Dhaliwal wall from Amplify Partners, we really aspire to be, you know, half the firm that amplify is in the long run. And just the the focus the value that they bring the thoughtfulness on the board, I’ve had the pleasure of being a Sunil on investment as well as working with his colleagues. Right Lenny my David over there, and Sarah continues to do amazing work like they’ve just built a world class team. They’re an incredible companies. So I don’t think you’ve had them on before I have right now he’d make an incredible guess he’s just seeing so much and he’s one of the good guys. So he would have a lot of fun in science.
You know, john, as you look to some of your, you know, inspirational other firms and folks that have either mentored you or served as some inspiration, I imagine you’re very focused on your 100 million dollar fund now and executing the strategy but what’s, what’s the future hold for workbench?
Yes, it’s funny, we get asked that I mean, when we were fundraising for this past, oh, my God, Is that a lot? I mean, are you trying to be you know, the cliched line was he trying to be more akin to like a benchmark or USP or and Andreessen and we love our swim lane. We love doing New York enterprise. We love this three to $6 million CT two category. So we actually don’t really have aspirations to try to build a multi billion dollar multi strategy wordfest we love being hands on with our companies. We love the pacing at which we operate and so we have so much fun and you know, thankfully at that scale you can you can do quite well so it’s not like we need to try to bolster billions of dollars worth a management fee so that that really is our aspiration to you know grow slightly as the market keeps evolving and you know, things get inflated a little bit but from a model perspective it is more akin to like an amplifier going back to my prior point versus going after like multi billions.
Jon, what do you know you need to get better at?
I would say focus I’m juggling, like all of us ensure a gajillion things at once. So just learning how to probably better stay organized, which is continually Oh, you’re trying new methods and just staying focused on on the task at hand and ruthless prioritization. So it’s a continual effort on my part. Life’s perpetual challenge, right?
And then finally, Jonathan, what’s the best way for listeners to connect with you and follow along with Work-bench?
Yeah, so I tend to be pretty active on Twitter. My handle is Fendien. And then for workbench broadly, I would highly encourage folks to sign up for our enterprise weekly newsletter goes out to almost 20,000 people every Friday we curate top news from the week we curate top fundings, as well as events that you should be aware of both in New York and beyond. So you can just go to work-bench.com and sign up for that as well.
Well, john, this was a huge pleasure. You know, congrats on all the success it’s great to see, you know, one of the good guys doing so well and one of the great firms, your entire partnership and staff, you know, having so much success, So congrats on that and looking forward to revisiting in a few years and seeing where workbenches at.
Thanks so much. It was so much fun being on today, and I appreciate the time. Thanks, Jon.

Transcribed by https://otter.ai