Jeffery: Welcome to Ask An Angel! And today, very excited to have you join us Kal because we’ve been doing lots of other things in the background. So even more exciting to kind of dive in and explore more about yourself and the business, and things you’ve been doing. So to start off, the best way is to give us a little bit of background on yourself, kind of where you’ve come from, where you’re at, where you’re going, and then one thing about you that nobody would know.

Kal: All right, that sounds like fun. So I actually started my career more at big companies like Wells Fargo Bank, and Visa, and Pricewaterhouse, and so did the fortune 100 executive thing but midway through my career I realized, I think I would have more fun on the entrepreneurial track. So from that I went to several real estate tech startups for many many years and soup to nuts, did all kinds of things when I reinvented myself that I was doing product, and then you know online marketing, and strategy, and so forth. And just had a grand old time just being an entrepreneur at several startups and then later, in probably about seven years ago, I got involved with an alumnus- alumni angel group called Berkeley Angel Network which is, obviously as the name indicates, an angel group four oven by UC Berkeley alone, which gave me my first exposure to the other side. And so, I’m been doing some angel investing through them and through other organizations, and kind of learned from the ground up how to do, you know, the deal flow vetting, doing due diligence, working with the startups to get them ready for pitch events and so forth, and through that I basically got embedded in sort the angel investing scene in the bay area. Connected with a group from Santel Angels that started an accelerator in Berkeley called Bachery, which now is five years in 12th Cohort, about 150 companies graduated. So I started as a limited partner and then over time I became one of the managing partners, and then CEO, and then I helped develop the curriculum in the program which really just gave me a good feel for: ‘how do you coach and train startups to succeed?’, and handed off day to day operations on that a few years ago, and then switched to another accelerator where we had another analytical framework to assess startups and, kind of rambling here, but.. very quickly what I’m doing now is a company called DealEngine. DealEngine.ai, which does analytics on startup success. So basically, think of it as the turbotax for startups where we collect a lot of data, crunch numbers, give quantified feedback back to the startups, as well as generating deal scores and team scores for the benefit of investors, and basically our northern light is, you know, the the elephant in the room with VC is that overall the industry has something like a 90% portfolio failure rate. So if we can use data science to de-risk startups from the earliest stage, and even get the success rate from 10% to 20%, we have a chance to disrupt the industry. So we’re in beta now and very excited about working with startups and just using data to help them get better.

Jeffery: I love it, and one thing about you that we wouldn’t know.

Kal: Okay, let’s see. Believe it or not I am also a Sundance nominated filmmaker because I produced a mockumentary short. Again, I couldn’t leave my roots of startups. So I did a mockumentary about the worst possible startup in the world, called Icevan.com, and made it to a few film festivals including Sundance which, god, if being a filmmaker could be a little bit more lucrative, I might stand that. But, god, I had a lot of fun doing that.

Jeffery: It was called Icevan.com?

Kal: Icevan. So think about: way back in the day, there was web van, and then we said, “What’s even worse than, you know, the worst of the worst?” So delivering bags of ice guaranteed in an hour, we almost did it about cinder blocks but we basically created ice van for, you know, the the company that delivers ice.

Jeffery: And that was the worst?

Kal: At least that’s the time, the best thing we could have come up with that, this was you know, some 20 years ago. I bet if we kind of brainstorm now and get really into non-fungible tokens, we can say you know, let’s have some NFTs for ice-

Jeffery: Yeah

Kal: -and it can probably get exponentially worse with some of the later technologies we have.
Jeffery: Well, just popped it in my head because I remember I was going through, I think it was Vietnam, and there’s you know, like a tuktuk. But it was kind of like a buggy with a bike on the front, but it was carrying a buggy and it was an ice buggy, and they’d go along every morning and everybody would come out at 4 or 5 in the morning, and grab their big cinder blocks of ice, and they had a little chainsaw, and they would just zip through and drop these blocks out in front of all the stores because they had to keep their beer cold. So that’s how they would do that.

Kal: That is awesome!

Jeffery: Yeah. So this guy would just literally drive around the blocks and just drop off ice, and it would go on. I think a couple times during the day and it would just be big cylinder blocks of ice, and then they would sit there with a pick, and then they would put their beer on it and everything else. But that’s how they delivered it. I don’t know what they charge for it but I remember that specifically because I was taking pictures of it. I thought this was a you know, great little business run and yeah it was pretty cool.

Kal: Well, that’s awesome! That actually tells me, maybe there’s even hope still for iceman someday.

Jeffery: 100% yes! Especially these hot climates where they can’t- the streets are too narrow or they’re- and they’re really just made for, they’re doing this on Yonge street or they’re turning them into- they’re reducing it down to one and one lanes for a certain extension and that way they’ll have more sidewalk sales, more people walking on the sidewalks, opening up. It’s not going to be like as much as it should be. I think they should open up all of Yonge street and get rid of cars on the whole street but then it kind of breaks traffic going, obviously east and west. But in saying that, like you know when you’re in Barcelona, you’ve got all of these major streets that are just completely shut down and they’re just walkable, right? And you have that in a lot of Portugal, you have them everywhere, right? And those are big bomber streets, so when you don’t have that opportunity, you got to move things around and that’s the only way you could get ice around. So I thought it was a pretty cool business model back then.

Kal: So I- yeah, you never know. I mean there is a market need for just about anything somewhere in the world.

Jeffery: Yep. I always just say that was that, I was in the Philippines because I have a company there, this was again, this instance was probably 15 years ago and we were at a golf course, and I was meeting with some business executives with my business partner at the time, and we went into it was a golf range. So we were having a drink and just teeing balls off, and it kind of hit me that there is a job in this world for everybody. If you’re willing to do the job and get paid for it, you can do anything you want and then it’s your decision if you’re going to take it to something of a different level.

Kal: Yes.

Jeffery: And I learned that there because as right or wrong as the environment was which it bothered me the time because I didn’t really like it, but I was looking at it from the entrepreneurship side is that there was a lady that was serving drinks but then there was also a lady that was teeing up the golf balls. And they would build them like just by hand and that’s how they did it, and that was their job and then you paid them at the end of doing that. So they didn’t use tees. They used this granular soil they would tee up enough to hold the ball on it and then you paid that person at the end of the day for all the balls you teed off, and you had to pay a certain amount of money.

Kal: So there you go.

Jeffery: And I thought: well, it’s actually pretty clever because they probably thought, originally, I should charge you for the tees and/or I could use a plastic one or I can create a job, and this person will just own this whole front field, and make sure everybody’s taken care of.

Kal: There we go. Yeah, to reach its own and there is a, you know, just because it doesn’t work in one market, doesn’t mean that somewhere else in the world it wouldn’t thrive just like you saw.

Jeffery: Exactly. So but I love the concept. I want to actually look this up. I’m going to check this out because I’d love to see that-

Kal: Yeah. you’ll find the video if you just go to Icevan.com. Up until recently, it actually, believe it or not, was a post-revenue quasi-profitable company because I just turned it into an Amazon Affiliate Site and you know, it was post revenue making about 20 bucks a month and and at least paid for hosting costs, which you know better than a lot of startups back in the day. I think it broke now, so you can still get to the video but unfortunately, I can’t monetize you right now.

Jeffery: Oh, that’s okay. That’s still awesome though, I love it. I love it. So there’s lots of little avenues and things that I want to touch on but I guess to go back to your kind of origination on where you’ve kind of come from, I think a lot of this obviously speaks to where you are today. But being through that banking sector and how you operate and function on that side of it, how much of those elements that you learned really do you feel a fit into what you’re doing today? From the financials, the marketing, like how you did things, do you think it kind of paved the way for where you decided to take that leap of faith?

Kal: You know what, I think I took a more unusual path than others because I started my career at you know, a conservative accounting firm where I was doing litigation consulting, and then a very fiscally conservative bank at that time, Wells Fargo Bank, and because I started off in finance, and really thinking about building business cases and financial models to you know, justify any initiative. I mean literally if you wanted a new coffee maker at Wells Fargo, you’d have to write a business case for it. So it kind of established a fiscally conservative discipline at my roots, which still you know, I sometimes had to reconcile with sort of the entrepreneurial side, which I don’t think I was ever as quite the taking a blind leap like some founders do that I would still try to apply some sort of fiscal or financial modeling discipline, and just needing a business case for the ventures I pursued, invested in, companies I worked with, that I tended to be a little bit more a pain in the butt just getting into the numbers, which granted knowing that founders early on will say, “Well, you know, these numbers are kind of made up anyway, can we just kind of ignore them?”. I said, “Well, yes. When we look back at this in two or three years, you’ll probably be completely wrong but this is still the best financial snapshot of where you’re heading, and it should be a good mirror of your staffing plan, your operational plan, your sales, and marketing plan, and let’s just see if it makes numerical sense if there’s any credibility.” And so that has actually influenced a lot of the models that we are developing now is just, ‘can you talk coherently?’ even if it’s going to change you’re going to pivot 12 times between now and two years from now. Just make sure that it’s coherent and that it’s credible. And I think that’s one of the things that’s really influenced me up until now and probably going forward as well.

Jeffery: And do you think a lot of that, like those kind of metrics and doing the case studies and learning or the use cases, learning about how to obviously raise funds to get a new coffee maker, do you think that really propelled your experimental side of things on how you can help startups really engineer and understand the startup? Because I do think a lot of the time it’s not so much like, “Hey, go build this model,” and it’s going to be completely wrong and it’s going to pivot. It’s more of the understanding that you can actually get comfortable and know how to innovate inside of a spreadsheet or inside of this metrics to come up with, “Hey, here’s where I’m really at and oh my god, I didn’t realize I was really here. When I thought about it, I was doing way better than maybe when I’m putting on paper and geez, I really need to go back and look at this” or “I don’t even understand how this works, and going, and getting that help.” Do you think that, that really, even in today’s world where you’re helping accelerate startups, do you find that pushing them into this modeling and understanding really puts a whole different perspective on their business and the future use case of this? That, “Hey, you know what, you might look good now but five years from now, this business isn’t really looking very good.”?

Jeffery: Yeah, I think you’re absolutely spot on. So I’ve had many cases where I’ve provided guidance and you know, you just sort of ask the innocent questions like, “Huh, this doesn’t make sense. This doesn’t reconcile with this,” and because of that they’ve affected some material pivots and changed their business model. So I’m here to ask the tough questions, when I ask for some of the data, you kind of have to also delineate between what’s a proven fact, what’s hard data, and what the assumptions are, and I personally always go in, “Well, you know, this industry has a 90% failure rate,” you know elephant in the room. So let’s assume this company will fail. So you can almost have a checklist, if it will fail: if …, and then just list out all the stuff, it will succeed if: …, and then you kind of need to distinguish between what are some assumptions you need to validate, what are you know hard data points now that still need to evolve over time. I’ve seen lots of cases where they’re absolutely convinced that you know, like CAC, customer acquisition cost, is one of the core key metrics and just because you’re crushing it right now in your CAC, right now is ten dollars but you’re in some B2B sas, you’re kind of playing the long game or the short game of you know, you can get a few leads right now and your CAC is ten dollars, but let’s fast forward and think about what your CAC will be when your top of the funnel inbound needs to be a thousand prospects a month, and you scale whatever sales and marketing campaigns because you’re not maintaining that CAC. So again, like you said you have to have sort of a forward-looking projection of you know, the entire ecosystem: who the competitors are, who are the incumbents that you’re just lodging, and so forth. So all these layers of complexity and just making them think about that in some ways is intimidating, but it’s sort of the things that they need to think about for like what the longer journey will look like.

Jeffery: And what I found from, I watched a lot of your videos that you guys put on in the early years of the Bachery, and I love them by the way. They’re very good.

Kal: Thanks.

Jeffery: Because they’re informative but and they were challenging, and you broke them down into nice little almost like a twitter feed which I think was great because it was just small enough for me to take information in, go back, come in, and I it kind of talks a lot to what we’re talking about now too, which is you know the things that can cause pitfalls or the things that you got to look out for. So kind of as you went through the banking sector and you started to build up these metrics, you’re also probably working with a lot of early stage companies even in on the accounting-banking side because that’s usually who’s going to banks right? And you’re- I find that operators in the bank side really just understand business in general a lot easier than the average person. And then when they do get in it, I find that LPs tend to always be a lot of them are bankers because they see the opportunity, so they want to get into that investment. So it’s either you’re a banker or you’re a lawyer. So lawyers get all the best deals and the bankers just have the risk analysis down, so they can jump in and figure it out.

Kal: Right, right.

Jeffery: So now, you went and jumped into the startup world, what were the some of the learnings you could take? And I know you got the top 10 list, top 12 lists, you’ve got these lists, if you were to give like five things that really changed when you went from corporate to startup, what were those big things that you were just like, “Wow, I had no idea that this was going to happen and I’m glad I learned this now,” and now you’re using these for your startups?

Kal: Yeah, so you’re saying the biggest thing that kind of blindsided me, I guess.

Jeffery: Yeah.

Kal: So one of the startups I was involved with, again, sort of you saw that I have this passion for independent film and so forth. So getting into that you know, just rubbing elbows with the folks at Sundance, and I went to some director conferences, and so forth. I mean I loved it. So one of the startups that I did after that was actually a two-sided marketplace which is supposed to represent the solution for distribution for independent filmmakers for the ones that go on the festival circuit. And I went very deep down working with the filmmakers, they loved me because I had a distribution solution that we were you know creating theatrical events in public venues that weren’t movie theaters. Like bars, and cafes, and restaurants, and so forth. And so they were the inventory supply. They wanted to get paid for it, and so I solved the problem for them but it was a two-sided marketplace, and so one of the mistakes I made was that then when I focused on the demand side, you know, I’d work with schools and I had this great independent film for children, and they said, “That’s great, but we really want to see Toy Story 4.” So it basically was the supply demand disequilibrium. So that got me then going to the studios, and I basically, at that point it was early enough that digital rights management and digital distribution was early enough that, am I allowed to swear on your show or? (Laughs)

Jeffery: You know what, yeah sure. I had someone else do once, so we just kind of kept going but you do whatever works. Whatever emphasizes works man.

Kal: We can bleep this out later but basically, I got from one of the studios basically, the thank you, f*** you document, which was their DRM requirements which were this thick, and something that we just could not bridge the gap between the studios, and then the audiences. So I guess what I’m driving at was in recent years I’m gotten very academic about the whole value proposition measurement, problem solution pairing, and just making sure that there’s the right product market fit, and that was one of those powerful educational things that even though I identified a big value proposition on one side, it was not the monetizing side and it sort of profoundly influenced me in terms of planning for making sure that you properly measure value proposition, and you do enough work on the customer discovery upfront just using some of the best practices with, you know, Steve Blank’s work and business model canvas and so forth.

Jeffery: So that value proposition, it is pretty significant because you know, you can’t- it can’t be off lopsided. Because someone will always demand more and then it can cause the whole business model to crumble especially, if they’re your first customer and they’re trying to help you move forward.

Kal: Yeah.

Jeffery: So when you were kind of, I guess, really diving into this and started to kind of feel, “Wow, wait a sec. This isn’t working out,” and you had a solution and now you got to bring two sides to it, and create this double marketplace, did they give you the window to do that or did it cause a bigger failure and that you weren’t able to overcome in the end?

Kal: Yeah, at that time. We were, you know, the other important lesson is timing. You cannot be too late, you cannot be too soon, you have to be at the right place at the right time. We were too soon. We wanted to do high definition at a time when streaming high definition wasn’t possible. We had to do it as progressive downloads, and caching them just to present- prevent, like you know, buffering issues and things like that. Plus, the studios just were not prepared to release their library into the digital realms, and you know, we were just trying to tap into the airplane release window. So again our timing was wrong and then we just did not have the product market fit at that time.

Jeffery: So does this give you, when you’re working with your startups and they’re coming to you with some innovative new tech, does this kind of give you more of a process for them to tackle these problems before they face them so that they’re not asking for Toy Story 4 when they’re only at Toy Story 1?

Kal: No, exactly. It’s- I’ll give you another good example is that when we have them prepare pitch decks. There is, you know, the market sizing slide which we all know, TAM, SAM, SOM, and TAM and SAM are pretty easy. They’re, you know, you look it up and you get some gartner report or something, you say it. It’s a 20 billion dollar market, done. Check. SAM is something similar, still top down. I push hard with my companies that som serviceable obtainable market, you don’t just say, “Oh, yeah here’s SAM and I’m going to take 10 or 1 percent of that and check them down.” Show me a bottoms up calculation, how you do the numbers, and showing that incredibly ties to your sales and marketing plan that you’re able to get into channels and distribution partners, and that you have the staffing and the resources to do it. And let’s do a real credible serviceable obtainable market, bottoms up with all those numbers and then you will have something that credibly ties to the other slides in your deck, other materials that you have in your deal room, and you can credibly go also because you have a lot of supporting documentation that holds up everything that you did. Anytime you come and say, “Ah, I think I’ll get one percent of this market. I’m done.” It basically holds no water for me.

Jeffery: I love it. I mean I was gonna say, if I was only recording this. Since we’re recording this that’s a perfect sound bite because I see that so often where the level of detail that doesn’t occur in that pitch deck or mostly in the process of sales is that it gets lost and then when they do get to that slide, it’s, “Well you know, I’m just looking for one percent to start.” But what does that one percent really represent? I think a lot of the time it’s never done as a bottoms up. It’s always bottoms- or top down and that just becomes a buckshot spray, and you’ve never really built any process into it. And I think from some of the things that I’ve learned that you guys are doing, is that you know buckshot spray isn’t is not going to be effective. It’s not going to work, so how do you get your teams to look at and again, this goes into those next investment layers and de-risking your business, how do you get the startup to really understand that if you’re going to go bottoms up and you’re going to be more articulate on how you’re going to acquire these, is there a process that you build in? So what does that repeat value look like? Can you build a team that does just keep cycling over repeat, repeat so that you can keep closing business and then just stacking resources and technology on top of each other, and that’s going to just keep closing your business and growing that overall funnel? Is there a process or is there ways that you guys try to structure that to get a startup in line?

Kal: Yeah, no absolutely. So a couple of things that are really important. So, and again we didn’t invent these things. These are just sort of academic best practices that have been taught that we’re leveraging as well. One is the concept of the beachhead: what is your initial market entry point that gives you the best chance for success and then the opportunity to move into subsequent segments or other verticals and so forth? And it is again a bottoms up exercise. The beachhead would just be you know, I consider it like the bowling pins. It’s the first pin, and then you have a bunch of other pins behind it, and maybe all those pins together represent SOM, and you have to check off all of those. So how do you pick your first beachhead? I hate to see the company that says, “Well, we’re SAS. So we’re going to do SME, and we’re going to do enterprise, and we’re going to do everything in between.” And the truth is, you can’t do everything because you only have so many resources. The sales cycle, if your enterprise, you know, if you were selling to me back when I was an executive at Wells Fargo Bank, the sales cycle would be potentially 18 months. It shrank a little bit now because of you know certain organizations having interest in working with startups. But it still potentially could be longer than the runway you have for your company before you hit your fume date. On the other side, the SME, it might you know be a good viable thing but your CAT could be so high that your either- your annual recurring revenues or your monthly it might require you, you know, a year and a half to break even on that first acquisition. So that’s where just geeking out on unit economics, just to know what makes sense, and can you just get enough traction to show credibility for the model and investors will forgive that? Or are you truly on your own and you’re gonna have to try to be self-sustaining and viable? So all these things kind of come into play, but ultimately just going back to the beachhead thing. It’s just making sure that you have all your ducks in a row that you can just hit a market, and then move to another sub-market after that, and kind of grow into that SOM as best you can.

Jeffery: So I love that. And what I love about it is that the bowling pin structure that you’re giving is that you have that first pin and then it spreads out but the thing is you’ve got to knock that first pin down before to lock down the rest. And I guess, if people can put that in their mind, they start to realize the rate. If I hit that first pin down which is my beachhead then that will open up the room for the next pins to be able to be accessible and then knock them down. What I find is that people are trying to line up you know, first pins like 20 first pins, and they’re like, “Well, I don’t know what my beachhead is and I’m just going to go after all of these.” So how do you coach a business that has the energy, the drive, the 18 hours a day, seven days a week mentality, that you need to work more effectively and just go after that one pin first?

Kal: Yeah, yeah.

Jeffery: How do you change that mindset because I think we’re all eager and that’s the- I think that’s probably the biggest problem versus the best problem, is that how do you get them to focus and say, “Look, this is your first time. I’ve done this a million times. You’ve really got to try and hone in on that one pin. Trust me, I’ll save you a million hours and I’ll make your life easier. Just go for that one pin and then the rest will be under, behind it which means they’ll all-”, how do you want to do that? How do you do that?

Kal: So I always say, I mean, first and foremost, the information that is in your prospective customer’s head is so much more valuable than the information that’s in your own head. So you do have to go out and do some field work, and the great thing is by identifying your target customers and first approaching them to say, “I’m doing a customer discovery exercise. I’d like to understand how you work, what your needs are, and have a conversation about that.” You’re not selling but at the same time you’re kind of selling because you’re planting the seed of your product in their heads, and then but it’s still a true market research exercise to just understand how they consume a product, what the incumbent product is, what it would take to dislodge the incumbent, which is absolutely critical. You know, beyond the cost of your product standalone, what’s the cost of just migrating? Are they going to have to have a team of you know a thousand people? Get trained and then they have to have a big IT program? So you have to kind of think of all these things. And so we have again, I’m originally a geeky spreadsheet guy, we have these worksheets which we just have a beachhead analysis, and you do a side-by-side analysis of different verticals you could go in, different strategies, and we just ask simple questions. You know, does your target in that segment have the money? Do they have the willingness to change? And you can kind of score it, and just you know it doesn’t give you a definitive answer, but it gives you some structured way of thinking about competing beachhead strategies, and which ones kind of filter to the top.

Jeffery: I love that. So one thing you said which really stands out in that was that you’re having multiple conversations and those conversations aren’t to close them today. They’re feeding the system to close at a later date but you’re putting this in their mind. So you’re going after this beachhead. You know you’ve got pins that are lined up behind each other and you’re having conversations with the pins behind them which could be in different verticals or different areas that you may tend to focus on because you’re putting the information in their heads to say, “I’m coming back. This is where we are.” So there’s one thing that I think I’d love to add in there that I think really will help in that mechanism which I’m sure is part of your beachhead process is that as you’re feeding the system, what you end up doing is, every time you gain a win that wind gets pushed back to the line, so it gets thrown back to all the other pins because what you’re trying to create is this herd mentality of interest. An interest comes from wins that nobody’s really jumping on board and saying, “Hey, I heard you lost 10 million last week. Where can I sign up?” But they’re certainly on board when you say, “I just closed Tim Hortons and you know, you’re working with that next coffee maker, a coffee company. And you know, they want in.” So those little types of wins build bigger wins with the next herd mentality. So you really do have to preface that sales funnel by getting out there, and getting the opportunity to make those pitches, and filling that information. In which eventually, you’ll continue to fill in and that’s that growing of that pipeline which is you know, you went to them a year ago, now it’s time to go back. But go back and –

Kal: Yeah, yeah. And to your point, I mean, once you get somebody and you basically want to basically use that as a case study to say, “Hey, I gotta win here.” What were the metrics of success? So when you’re selling something, you have to be able to say, “What’s in it for them?” If you pay me, you know, a thousand dollars a month for the SAS platform, you will get a 30% boost in employee productivity. You will have a 25% reduction in cost. Whatever their business case is, you actually need to understand that as well and be able to derive those KPIs because that becomes critical for your marketing materials as well. You know, read our white paper or case study, customer x had 25% reduction in costs by using our tool. That’s much more powerful, plus you get the testimonials. And somebody else saying that you’re great is so much more valuable than I saying that I’m great myself because you know, who am I to assess myself.

Jeffery: Well, I think you’re doing great. So keep it going, and outside, you mentioned KPIs. Maybe you can dive in a little bit more on what that KPI structure would look like as a win, not just for the internal of your teams, and your business but what those KPIs will represent to the public. When you’re sharing those out, what type of things do people want to see so that they can get on board? And you mentioned some testimonials, what other elements really bring this home for customers to start onboarding themselves and not even bothering with you?

Kal: Yeah. So actually, one other thing, I’ll just share that sort of helps set up this as well as this is part of our curriculum as well, is that we very much believe in doing pilots with customers. So you basically want to de-risk it for the customer as much as possible. So but you have to have a predetermined beginning and end. So let’s say, it’s a finite period of time, 30 days, 90 days, whatever, and you need to have a commitment. Well, if I hit these KPIs, what happens? Well, you become a paying customer. You’re going to pay this and maybe because you’re a beta customer, you’ll get a 20% discount for the first year yada yada. But also, that we can use your KPIs to measure the successes. So part of it is just whatever the KPIs for the customer is and it always depends. It’s usually things like productivity gains, savings, cost savings, and so forth, or better customer acquisition, measures like that. So I focus more on our, like the success kpis for the startups, which at the end of the day, again this is sometimes a gross oversimplification, but I always condense startups to basically every startup out there just sells widgets. And you monetize the widget either one time, once a month, once a year, once a quarter, something like that, and there’s a certain cash flow stream. Then you have the upfront acquisition costs, you have churn rate. Churn rate is absolutely critical and basically, getting into that transaction with one customer. To me, is like a building block of how you build up your business, and you have to show that, okay customer x has this kind of profile because I can acquire them. I break even on customer x by the fourth month. It has a lifetime value of y and you can show that like how it rolls together, if you get a bunch of building blocks to the entire PNL of your company. At least on the margin from acquiring more customers with that profile. So it’s a little bit of a simplification because I- there are lots of models that don’t apply to that but at the end of the day, cash is king. Show me how you spend the money, and how you recoup the money, and show me in a way that you can get up to the profit margin that you need to have a sustainable business because you also have to cover fixed costs and so forth. Show me when you can break even on a per customer basis, you know, that lifetime value and like I said earlier, churn is one that is too often ignored, and I can’t tell you how many times, I probably guess, the first iteration of a financial model that I see from a startup, half the time they have not built in churn. It’s just, you will lose customers. You cannot pretend that you’ll acquire a customer and keep that customer forever. And as a startup there’s a very good chance that you will have worse than a 25 churn rate annualized. And so, if you’re not taking that into account and all I have to do is flick one thing into your model, and I can completely blow up your model, that means you have to think about it. And so you can’t say, “Well, I’m only going to have a two percent turn rate because you know, some of the, you know, Google is going to lose customers today.” Believe it or not somehow, Google will lose customers, and you’re not better than Google. So take into account how to retain the customers, and also just remind founders that it is so much cheaper to retain and do more work on the retention side than on the acquisition side. And those are the little things that you know, you don’t do it once your- once the ball’s in motion. Lay that foundation early on at whatever way you can.

Jeffery: And that brings in that repetitive, you know, that auto on button that just keeps repeating right inside. You’re building off the same metrics that you close the beachhead with, and then you’re just repeat repeat repeat, muting the same style, maybe tweaking it here, and there but it’s just that auto repeat.

Kal: Exactly.

Jeffery: So now let’s take- we’ve gone through this you know data, the bowling pins, getting into the information, mining that information, building KPIs, selling the product, getting into market, crushing it. Now, let’s take the first question what we asked and let’s put the brakes on and say, now everything that you’ve learned being in startup world for the last 10 years, what would you go back to big business and say, “Hey, you’re really doing this wrong.”? You learn a ton in startup world and I think it’s a total different understanding than how big businesses is doing it. So what advice would you go back to big businesses and say, “Hey, you know what I learned a lot when I got into the startup world. I got punched in the face here by this instance. I learned about double marketplace and how to make things roll.”? Now, take the other side and go back, what would you bring back to big business and do over?

Kal: So actually, some of the very things that I just told you about like, you know, using tools like the business model canvas, and customer discovery, and the value proposition canvas. I’ve actually been retained to do bootcamps and workshops for large international corporations that will also want to do that internal innovation thing that it’s clear that a lot of corporations want to dance in the space and in some ways they might set up either an internal innovation group, or you know the intrapreneur program, or some other skunk works, or what have you, and at the end of the day, I’m yet to see where it’s blossom. I’ve seen a few actually, and we have a couple of case studies where they’ve, like I think boeing had like its own special skunk works program for a jet and so forth. But generally speaking, a lot of the corporations that I’m come across will give some lip service to it and try some things, and then at the end of the day, one of the other important ingredients that startups are actually good at is you know, doing more with very few resources and then being nimble and quick. So when I was at you know one of my fortune 100 jobs, I actually launched a product development process globally for the company, and it was sort of the academic classic six stage-gate development process. You know, it’s sort of like you know the the what you were taught in business school, and now a days you know with lean startup and with agile development, you know, as long as they have enough resources they will still operate circles around you. So that framework, you cannot have sort of the disciplined six stage gate process which means that it’s at least 12 to 18 months to get a product to market. And in spite of that, I mean historically, the product launch success rates were not any better than the lean ones. The better thing about lean is that you can iterate quick, and hopefully pivot during the customer discovery a lot. So you still have to have a concentrated area of failure, and just to you know fail quick and then move on, and fail in a way that you don’t kill your company. So that’s the thing that I would love to impart in companies in larger like corporations and I’m yet to see first hand where it actually flourished in a way that they absolutely embraced because at the end of the day they still have to interface with other, you know, silos within the company that just inherently bog down the system and slow it down. So I would love to see it. I still think the best way for corporations to interact. There are still great ways. I mean, they could still sponsor you know accelerators. They could do skunk works, they could have a corporate venture capital arm. So there are lots of ways of dancing around it. I’ve yet to see like the perfect case study of, you know, innovation moving things quickly when it’s, you know, still deeply embedded within sort of legacy systems.

Jeffery: I love it.

Kal: I hope to be proven wrong.

Jeffery: In time, in time. But I do love that and again it’s a good way to circle back because you’ve taken different learnings and said, “Hey, wait. There’s something here that you’re not doing,” and I’m learning it, and I think it’s it could be setting up an outside infrastructure that lets them run on their own like a little mini entrepreneurship camp, or if it is going to be internal you really do have to find some real driven metric based team that’s going to be winning above what they’re normally structured to do in big business because that protocol and process side throws things down because they’re always mitigating risk. And I think there was some crazy number, like it’s 72% percent of all internal corporate projects fail, and I think it always falls back to the person driving it because they never get to the end lengths because they don’t envision all the moving pieces. They just envision the end goal. Try to work their way back and never really figure out how to get there because too many moving pieces again caused it to break down.

Kal: Yeah, exactly.

Jeffery: Well, it’s fascinating. I think there’s a ton of learning there. We’re going to kind of keep moving our way through but the next thing I want to chat within and we’re- there’s always this one you know, all the startups and I think you guys have worked with over a thousand startups now through the accelerator side. So you’re probably going to have a probably a hundred stories about this but would just need one or one that pops in your mind. And we’re kind of looking for that story that really kind of just makes you feel like that’s what it takes to be an entrepreneur, and it could just be anything. Where you know you had a female founder that had to go through these things, and then just made an amazing company or didn’t or this guy had to do this. It’s kind of that one where you’re just sitting there and you’re taking the story and you’re like, “Wow, that’s incredible!” I always like positive, real driven, can’t believe they made that one through. Anything that comes to mind?

Kal: Let’s think. So just the go-getter. We do have one company that was in Bachery. A real estate tech startup that probably the most driven, well-organized founder, absolutely systematic with engagement, communication, and just completely buttoned up that really, it’s what you want in all founders because I’ve, you know, worked with a lot of founders that aren’t particularly communicative or they’re communicative until they get your check, and then it’s sort of like, “Oh, you’re in the news,” and then you email them and they’re like, “Hey, how are you doing?” But aren’t giving updates. So it’s that, first of all, that if you were to email them, they’ll get back to you like, within 20 minutes even if it’s 11 o’clock at night or something like that. It’s just like they’re always on. They’re passionate. they’re driven, they’re- they have the right level of transparency, and just know how to work the system. And so the one finder that I’m thinking of that was so systematic of in communicating. I’ve actually used as an inspiration for myself as well because there is something there where he had assistants that basically managed Linkedin and so forth. And still, I mean he didn’t farm it out. He’s still very personalized and communicative, but it’s just made the communication at an art form in terms of engagement.

Jeffery: I love it, and you’re bang on that the tough thing about not just being in startup world but just in general, when you’re growing that business that communication becomes the lacking piece because you’re always head down, working hard, and I think others forget that they’ve got investors all throughout the stages, and that everybody’s looking for information. And if you don’t feed it then everybody’s coming to you which means you’re creating more workflow for yourself. So the easier way you can be systematic and push that out will save you a lot of effort on this side, and allow you to keep moving forward, and even if it is your head down at that point.

Kal: Exactly, exactly.

Jeffery: I love it, and it’s a very valuable lesson for startups to pay attention to. We’re going to jump into our rapid fire questions.

Kal: Okay.

Jeffery: All right, first question. Why do you invest in startups?

Kal: Diversified portfolio, basically, you know, some of the money is in conservative stuff and some is just going for the home runs. But more importantly I love this space. I want to be an entrepreneur and investing in companies then empowers you to live vicariously through companies that are doing the kinds of things you want to do, and you know, sometimes you get to be a little bit more hands-on. One example, and like I said, it lets me do things that I’m not qualified to do. So another one of my passions beyond filmmaking is actually, spirits. So I tinkered with some technologies to artificially age spirits and turn a white spirit into a brown spirit like in a week, and I did it myself. I got like pressure chambers and did a lot of research and there were some out there. And it looked great, it tasted like crap. So I basically, connected with somebody that’s sort of on the cutting edge of this called lost spirits and they’re going gangbusters. They’re opening up this huge facility in Vegas now, and so as soon as I saw what he’s doing with his reactors, I realized, “Wow, he’s working at a level that I could never dream of doing it.” So I might as well be along for the ride with him and you know, get to see his successes and, you know, I kind of gave away my.. Actually I gave away my equipment to a different startup that used it for a different use case. So, you know, it’s like I said just having it fingers and a lot of fun pies.

Jeffery: I like it, that’s awesome! How did you get started investing in startups?

Kal: So actually, it predated Berkeley Angel Network. It was basically a friend of mine starting a company and so it was like sort of, “Hey, you want to help here?”, and like, “Okay.” And then the important thing was the distinction between, for lack of a better term, dumb money because you know, first efforts were like dumb money versus being exposed to, “Oh, this is how you do it at an angel group,” and there’s a screening committee, and that’s- this is how they review deals, and this is how you do due diligence, and just being on a due diligence team to teach me about best practices. I think that was absolutely invaluable to just make sure that you not only do it for the love but that you effectively, you know, de-risk it for yourself as you get into it.

Jeffery: I love it, and your favorite part of investing?

Kal: Working with entrepreneurs, honestly. It’s sharing some nuggets of wisdom even if it’s my failures that cause some sort of pivot or course correction that wouldn’t have happened if I weren’t there, that to me is like one of the most gratifying things.

Jeffery: Perfect. How many companies do you invest in per year?

Kal: Personally, it might be fewer than like five or six. And then through Bachery, it would be, I guess, we do about two chords. So maybe about 30 or so.

Jeffery: Well, you’re way above average. So it’s awesome.

Kal: Yeah.

Jeffery: Any verticals you like to focus on?

Kal: So I’ve always said I’m vertical agnostic because I like to go where the opportunity leads me. I mean, the last one I did was a life science one, a dental one. And again, it was where I have no domain expertise. I’m not qualified to do life science. I have to rely on people that are smarter than me. So you know, jokingly, I like to say I like to just invest in pre-unicorns but you know, I don’t expect the unicorn. But I just look for those that are the best upside potential. So I’m not swayed by the flavor du jour be it, you know AI, or VR, AR, or whatever. It’s investing in things that have identified a product market fit, have some sort of unfair advantage in the marketplace, and then could succeed by just, you know, the sheer execution. So and you know, it could be anything.

Jeffery: I like it. I also felt very marketingostic, and then after five years, I went and evaluated what I invested in and I realized that it happened to be just the areas that I did a lot of stuff in. so as much as I thought I was like, “Oh man, I’m all over,” and then I looked at it. I’m like, “Damn it.” So I guess you tend to bend to the things that you really understand because it’s faster for you to say ‘I like that’, than it is like you said, going into it, maybe you learned more from an angel group you saw some leads you’re like I’m into that. So it kind of progressively, you keep learning, right?

Kal: Yeah, exactly.

Jeffery: So in the due diligence side, is there certain areas that you require in order to make an investment in the due diligence process? If you don’t have it, you’re out?

Kal: Generally, I personally do not like the, you know, ‘hurry the clock is ticking. There’s a mad feeding frenzy on this one. Come in and we don’t really have much in our deal room for due diligence.’ I- like I said, I actually like to look at the numbers not because they’re right. I know they’re wrong but it’s just that they’re credible and cohesively tie together the entire narrative. So I’ve passed on companies that I went very far along but I just did not see the the the hockey stick that you’re supposed to see. Whatever way you model out the hockey stick. It has to, you know, the ingredients to the stew have to corroborate that, and so I ultimately want to make my own conclusion not be pressured into, you know, ‘hurry time’s limited we only we’re about to close in a week!’ I just, I’m not swayed by that.

Jeffery: I love it.

Kal: I might miss out on things here and there, but c’est la vie!

Jeffery: I think the- no problem in the world has to be solved in 10 seconds. I think you always have some time and if you can’t find the time, then it’s not worth the hustle because I think, it’s the pressure doesn’t create the value. So..

Kal: Yeah.

Jeffery: I wholeheartedly agree that. Outside of paperwork, and are there other things, factors you mentioned, obviously the entrepreneur, so is that kind of the number one factor that gets you involved and then that’s it? Or there’s team or is there process?

Kal: So overall, one of our other investment philosophies is, you know, generally startups fail but we also know why they fail. So a lot of the studies have shown that team, to your point team, and product market fit account for 80% of startup failures which is one of the reasons within our deal engine analytical framework. We deconstruct to focus specifically on team, product, market, and money. And those four separate drivers are measured and assessed. I’ll double click on the team thing because that is absolutely so important. I have worked with founders in the past that granted there’s something called coachability, which every founder needs to be coachable. I- you know, even though I’ve got lots of gray hairs, I’m coachable as well. I need to be able to take in feedback from multiple sources. Some of the advisors might contradict each other but I take it all in and can process it. I have worked with founders that are not coachable and they just argue, and I can give stories of, you know, arguing that they’re going to defy the laws of advertising physics, and achieve a better, you know, cost per action result than some of the best, you know, marketing PHds out there, and somehow perform magic arbitrage on like, you know, google adwords and thing or adsense and so forth or adwords. And what happens then is they fail in the portfolio, and then we’re like, “I was not surprised that happened because they literally argued with me about things that didn’t make sense.” So team is an absolute critical one and so some of the work that we do at deal engine is that we do a lot of analysis. Not just on or we try to avoid some of the analytical self-fulfilling prophecies that are demographic stuff because you might get into a cycle where it’s like, “Oh, look. Here’s some dudes that graduated from Stanford and then got a job at google. They’re the best profile for startup founders.” We know that entrepreneurism thrives across the spectrum and there are other measures even in psychometric measures, things like emotional intelligence, grit, visionary skills, salesmanship, and those are the kinds of things that we actually are systematically measuring now to just make sure that the team itself, has the right psychographic profile that aligns with what a successful founding team would need to succeed.

Jeffery: Awesome, very well shared. Do you like to lead rounds?

Kal: Yeah. I am personally a follower.

Jeffery: Okay, do you have preferred terms? Like press shares, common shares, you’re pretty open.

Kal: I’m open to all of the above. I tend to sometimes negotiate. I sometimes prefer not just being the passive investor along for the ride that I do ask, you know, “I’d like to be on your board of advisors.” I think that’s one of the things that again data shows. Companies are more successful and are more likely to succeed if they have more engagement with investors and advisors. So this was from an angel investor return study a few years ago, a multi-year study thousands of angel investors, if the founding team only engaged an average of twice a year with their advisors and investors and advisors, they are three times less likely to succeed than if they engaged twice a month. So that engagement actually happened, helps just because it provides that diversity in perspective and just learn from our mistakes that we will see things that, you know, sometimes that you know they’re bored with that they might engage with might not have that same focus. So a good well-rounded board of advisors is absolutely key.

Jeffery: I love it, and wholeheartedly 100% hands down agree with that. The numbers show it prove it but the founders just don’t tend to look at that as a opportunity just like we don’t tend to look at it that all of these people on a board or investors, are actually a gateway into more sales, more opportunities, with the- for the business. And I think that somewhere that education needs to be ramped up and changed because you brought these people in, figure out how to utilize them. They’re key assets and they’ve got a ton of experience.

Kal: Yeah, well, we totally teach that. Every like, in our course, once a month give an update and end it with: ‘here’s my ask of you; here’s what I need of you; I need an introduction to somebody in you know enterprise sas; just make one introduction this month or give me to you know, one investor.’ If you don’t ask, you’re not going to get those resources and you know, that’s what they’re there for. They want you to succeed.

Jeffery: Agreed, yep. I’ve been learning that one. If you don’t ask, you can’t get it.

Kal: Yeah.

Jeffery: And it’s a lot easier to ask than it is to do it yourself.

Kal: Yeah, exactly.

Jeffery: Do you take- do you do follow-up investments?

Kal: Yes. Yeahk, well, it depends. I like them when they’re available and if it makes sense.

Jeffery: Perfect. Awesome, well, we’re gonna shift a little bit more again. One more shift into the personal side.

Kal: Okay.

Jeffery: All right, thank you. That was great. Okay, so first personal question: what is your superpower?

Kal: My superpower.. it’s probably geeky but the spreadsheet thing is one thing that has not left me. I think it was such a formative thing that quantifying just about anything is my natural thing that if there was a task to get into, I would typically still start in a spreadsheet, and you know, whatever it is. If it’s a sales funnel, some sort of waterfall analysis, it’s just my impulse is to quantify it. And the other one, that I guess you already asked for once. I’ll stop there.

Jeffery: No, fire away! Keep going. This is good.

Kal: I’ve always had this knack for having the ability to see disparate connections and bringing them together. That’s it’s, you know, if it’s somebody to help the company, or it’s a new market opportunity. So it’s that out of the box thinking that I don’t know, you know, it’s helped in that I’ve introduced new random disparate business models to companies and they’re like, “Huh, we didn’t think about that.” Which is always fun too.

Jeffery: You’re all-around full-fledged problem solver.

Kal: I try. I’m a student of the whole problem solution value prop. So that’s, I live and breathe for that. In fact, I teach a course called “What’s your problem,” which is all about problems. So yes, I guess you’re spot on.

Jeffery: Yeah, I think that might fit. Then yeah, I like that. That’s awesome. You can’t get any more lined up than that I guess. Much streamlined. Okay, so what’s your first your favorite sports team?

Kal: Oh, the San Francisco Giants. Big baseball fan.

Jeffery: All right, all right.

Kal: And actually, and the Golden State Warriors. I’ll do- I’ll cheat, I’ll say that too.

Jeffery: That’s okay. That’s all right. They’re not a bad team. The Raptors I think would, well, this year they’re not so good. But last year they could have done something. Two years ago, two years ago.

Kal: Well, the Raptors, we still have some painful memories from that series. I’m getting over it slowly.

Jeffery: You guys had some amazing games and somehow we pulled it off. So at the end outside of that one injury that happened at the very end-

Kal: Yeah.

Jeffery: Pretty tight game, man. I’m not even sure how we pulled it off. So either way-

Kal: No, I was happy for the Raptors and more happy to give it to them than the Cavaliers or any Lebron team but so be it.

Jeffery: Very true, very true. Okay, favorite movie and what character would you play in the movie?

Kal: Wow, my favorite movie, probably the one that is probably the best cathartic moment of all time was Shawshank Redemption, which was, you know, the prison movie and can I choose not to be anything in that movie because that was like pretty grim movie to like live through. My second favorite would be The Matrix which I think was just brilliant, and I would pick Neo from The Matrix. If I could be the one.

Jeffery: I’ve actually, in all the interviews I’ve done, a few people have actually picked Shawshank. Like just like that, just like you did, you’re just like shotgun and I was like, “I have to go re-watch this movie. I’ve seen it many of times but it’s been a long time.” But I’m gonna actually look this up on my watch tonight.

Kal: Watch it.

Jeffery: It is a great movie.

Kal: It takes you to the depths of hell and miserableness but then again, if you haven’t seen it I don’t want to give away the punchline in case people haven’t seen it. But it is the kind of movie that just gives you that emotional lift and just the down and the up are just made the experience amazing.

Jeffery: It’s kind of that the world of going through defeat in the long play. Letting everybody feel you’ve been defeated.

Kal: Yeah.

Jeffery: And then in the end, you actually were planning this and you won the whole time. So yeah like, have you seen the movie Papio?

Kal: Yes, yes.

Jeffery: It kind of has that same resemblance.

Kal: Yeah.

Jeffery: You’ve beat me up, you think you’ve won, but this whole time I’ve been living in my own head and I’ve actually left a long time ago.

Kal: Yeah. Exactly, exactly.

Jeffery: Yeah, that’s pretty cool. I love it. Very cool and of course, Matrix, always sick and it’s a- Neo is a great character in that. I haven’t started that series over, but I do like to late night go through old series and I just watched them over and over. Like finding old series that I haven’t seen in a long time and watch them. So I finished just recently doing, oh my god, now I’m gonna have a brain fart on it. I should have just said it, you know, when you’re popping your head and then you forget what it was. There was- there’s five.. Underworld. Have you seen The Underworld? It’s the vampires and werewolves, it’s called Underworld.

Kal: Yeah, I have to admit. I have not seen those.

Jeffery: Oh, they’re awesome.

Kal: I’ve never been a vampire person. Like I just have not liked vampire series for some reason.

Jeffery: This one is really well done.

Kal: Okay.

Jeffery: Probably, one of one of the better ones I find that have been ever tried to accomplish this and they use tech all the way through and the technology just gets better and better from when it started to where it ends. But either way I went through that one and I just finished. It’s been a few months of trying to get time to watch it, and now it but, again, very well done.

Kal: All right.

Jeffery: All of the movies. There’s four or five of them but they’ve done a pretty good job.

Kal: So I will tell my wife that this might be a weekend binge watching time.

Jeffery: Well, you gotta like them. So you gotta like werewolves and wolverines or werewolves and vampires, but it is good.

Kal: Okay, okay. Dearly noted.

Jeffery: But Kal, I want to thank you very much for your time today. I learned a lot and like I always do even though I try to get away from taking notes. I can’t help it. I hear great things and I want to write them down so that I can talk about them after, but brilliant. I love what you guys have done, and again, it was great to spend some time and to learn more about how you think, what you’ve been doing, and how you’ve got to where you are today. And the way we like to end this show is we like to leave you the last word. So anything that you want to share to a startup or to investors. I leave it to you but again thank you for all your time today.

Jeffery: Absolutely. Thank you for having me JP. My last word is, in case there are startups that are within earshot of this, so DealEngine.ai is taking applicants into our beta program now completely free, non-dilutive. And all we do is we help you provide some mentorship, take some data from you, and do some analytics. So go to DealEngine.ai/beta, and tell them, Kal sent you through JP’s show, and hopefully we can help you succeed.

Jeffery: I love it, awesome.

Kal: Awesome, thanks a lot JP! It’s been a pleasure.

Jeffery: Have a great day! Thanks again!

Kal: You too. Take care! Bye.

Jeffery: Oh, that was brilliant! Great job by Kal and shared a lot of great information. I love the bowling pin analogy. Just by the fact of way you can envision rolling those pins and especially in that sales cycle, the beachhead being that number one pin, hit that down and it knocks the rest. I think that was just well shared out and I think startups, investors, really need to hold in on that side of things when it comes to your business, ‘how do I set it up so that I can get that first pin lined up, so that I can keep auto repeating and hit that button, so it just keeps occurring, occurring to bring that in?’ I love the Shawshank movie. I am going to spend some time to watch that and then, of course, I think on the other side where he talked about DealEngine.ai. I think that that’s another great platform that they’re putting together. So at the end, build your kpis, build your funnel, line those pins up, knock them down, and then just keep auto repeating. Thank you again for all your time, everybody. Like us, share, add us on Facebook, Linkedin. Looking forward to seeing you guys all soon again. Thank you.