Sales Strategies and Founder Insights with Jeff Whitlock

Full episode transcript

Alper Yurder: So today in the Therapy Chair, we have Jeff Whitlock, who is the founder and CEO of Grain. We'll talk about his success, the joy, the pain and the journey. So welcome to CS Therapy. How are you feeling today, Jeff?

Jeff Whitlock:Yeah. OK. Good, yeah, really excited to be here. Thanks for having me on.

Alper Yurder: My pleasure. You're one of those founders that I follow with great joy and excitement. You bring fresh perspectives, you share the highs and the lows, and you really share your observations like data -driven insights very candidly. So I think we're going to have a good chat today on the show, hopefully. But before we talk any business at all, obviously this is sales therapy, and any good therapy starts with childhood and growing up years because it shapes the person we are today as a person as a business at work, as a person at work, as a person at business. So let's talk about that a little bit. Like, where did you grow up? How was the growing up experience for you?

Jeff Whitlock: Yeah, so I grew up in Utah and Arizona. I'm the oldest of seven kids, which has probably a lot to do with kind of who I am. And I grew up in a rural community on like an acre and a half and spent a lot of time, a lot of time hanging out with the animals, traveling, camping, and working on the, working on the property.

Alper Yurder: This is a little bit of a shock to me because it's not our first encounter and we've had some really great chats. See, this is why I asked the question. You never strike me as the type who grew up in a farm with seven, like between seven siblings, you know, you you strike me as the I don't know, like the guy who grew up in urban New York or whatever. I don't know why I have that impression of you, Jeff.

Jeff Whitlock: Interesting. Yeah, no, definitely not urban. We were in rural Gilbert, Arizona. We had like goats, chickens, pigs, a bunch of an orchard and yeah, no, like kind of a yeah. Yeah. Yeah, to some degree. I mean, I don't miss the work every Saturday. I mean, it's a lot. It was a lot of work. Yeah. My parents in hindsight, like it's really grateful for them to kind of do it, but it was it was tough. Yeah. It was like every Saturday we did a lot of work to kind of maintain the thing. So.

Alper Yurder: Tell me now, do you miss it? Do you miss the pigs on chickens? No.

Tell me about it if you don't mind a little bit. Like I have never grown up in a farm, rural area, whatever. Like all those things are new to me. I'm an urban, I'm an Istanbulite from the big city. So tell me the life of a farmer boy.

Jeff Whitlock: Well, it's not a farm. It's like, you know, I mean, there's big farms that we just had sort of like a, you know, like more of an agrarian property in agrarian community. So it's like, so yeah, it's like we spent time. Like I said, we had an orchard. So you constantly trimming the trees, picking the fruit. We probably had like 45 trees, 50 trees, something like that. And then, you know, orange trees, yeah, naval oranges. Yeah. And there's on a, they say in Arizona, there's five seas and citrus is one of them. It's actually a.

Alper Yurder: What please?

Jeff Whitlock: great place for growing citrus. But anyway, so then, you know, and then spend time. So spend time a lot of time like pulling weeds, mowing lawns, you know, the worst is leveling, because like my family was really cheap. So we didn't have a tractor. So like, you get like this, the property can get like really like rocky and bumpy. And so you use shovels to level it to like make it flat. It's like, yeah, get calluses. So it's good, but it's good stuff. Yeah.

Alper Yurder: No. Okay. So they made the seven kids just like good old days for the labor, basically.

Jeff Whitlock: Yeah, I mean, it wasn't like cruel or anything. It was like, you know, it was like four hours every Saturday, four or five hours every Saturday. And then after we're done, we could go play. But I think my parents did it really deliberately. Like they wanted us to learn the value of hard work.

Alper Yurder: That's the idea. Okay.

So now comparing the work back then to the work you do as a founder like which is non -stop and this is not your first rodeo. Which one which one do you pick? I guess your current life, I guess.

Jeff Whitlock: I mean, that's why I'm a founder. So it's easier. I mean, in some ways, honestly, that is kind of the thing that's nice is like, so I had that experience as a child. And then after, during college, I worked in construction. I was a construction worker and like those two experiences, I'm always, you know, I like, well, occasionally pause and reflect on those and like, Hey, I like what I'm doing. As frustrating as it is at times, it's like, I like this a lot better. This is a way better gig. And so it gives me that appreciation and perspective.

Alper Yurder: I think it's such a funny thing. Like, I mean, obviously I've been a university and hard worker and white collar and all that. It's just office work. You don't do anything like manual, like proper human job. And I just bought my new house. This is actually the second time I'm shooting from the new studio, which is my in my new house. Yeah. Yeah. Yeah. You're my second second guest in the new house in the new studio, which is my bedroom, basically. Right.

Jeff Whitlock: Yeah. Your new house. Nice, cool. Congrats.

Alper Yurder: And my point is I'm doing DIY for the first time in my life, like actual work with my hands and I'm loving it. But if I did it as work, of course it's really tough. All those people who do it day in, day out, it's very demanding.

Jeff Whitlock: Yeah, I mean, there is something like very presencing about it, you know, where you can just get in the flow and like, it really connects to your body. But it's also if when you do it as your profession or regularly, it can be very, very exhausting and monotonous a bit. Yeah.

Alper Yurder: Absolutely, I agree. So great, so you grew up and then like high school, university, like when did you start moving away from that family house?

Jeff Whitlock: Yeah, so I went, I moved to California for university. And then I went to this school called Occidental, which is like this like liberal arts college. It's claimed to fame is that Obama went there for a couple years before transferring to Columbia. So that was fun. And then I went there, I played football and studied music composition. And then I, then I actually left the country for two years.

Alper Yurder: How annoying.

Jeff Whitlock: In my faith tradition, we do this thing called the mission, where you like go and you spend two years in another country. So I did that and I served in West Africa. So I was in Sierra Leone and Liberia. And then I came back and I transferred to Brigham Young University, which is a university in Utah, where I finished my undergraduate degree.

Alper Yurder: How was the mission experience? Was it humbling?

Jeff Whitlock: There's a lot of things, honestly, like humbling, perspective expanding, life, you know, life changing, lots of words you could use, but yeah, it was amazing. I mean, we had been, I traveled to Mexico a couple of times growing up, but hadn't really been exposed to a very extro, very different culture with, you know, I would say with basically a lot of poverty, a lot of poverty, like lots of poverty and poor infrastructure and.

Alper Yurder: Different. Yeah.

Jeff Whitlock: Yeah, it was amazing just to spend a lot of time with people from there and get to learn to love them and become brothers and sisters with them. But also just see a lot of things they could teach me and that we're all still humans despite all the differences.

Alper Yurder: Yeah, no, I love that. Wow. That's a great experience. I guess in the States, and a lot of my guests are from the States, obviously, it's a very, how should I say, supposedly it's a multicultural culture. It's a pluralist society and all that. But at the same time, it does feel quite conservative and like in inner looking.

Jeff Whitlock: Yeah.

Alper Yurder: So I guess getting out of Arizona, Utah, whatever, and going to those places, it must have been, and you are young, it must have been quite an interesting experience for you. Like, you know, these people are quite different from me, but then you start figuring out the similarities, I guess.

Jeff Whitlock: Yeah, yeah.

Yeah, totally. Yeah. I think, I think this happens a lot when you go into new environments is you're, you're, you know, as a, as a, as a species, we evolved to like look for threats and, and we're attenuated to differences in our environment in case it is a threat. And so when you go to new place, you're very focused on like all the differences and that's why people have culture shock. But then once you get past that, you see, wow. Humans are actually really similar wherever you go. I really believe we all are way more similar than we're different. We have very similar needs…

Alper Yurder: Yeah.

Jeff Whitlock: …desires, values. And so yeah, that was a great experience in that regard. And then...

Alper Yurder: Yeah. Yeah. We're we're a species trying to figure out and I was watching I don't know if you've seen it, but there's this Netflix show called The Three Body Problem and it's about. you've read the book. I wonder. OK, great. Well, you might be OK. I shouldn't give any spoilers then, I guess.

Jeff Whitlock: I haven't watched it yet, but I've read the book a bit. Yeah, at least the first one, yeah.

Okay, yeah, yeah, yeah, sorry.

Alper Yurder: But I love sci-fi and I love the things that explore the human species, like, you know, things like interstellar and how they connect, even like alien, how it kind of connects to the human nature and the psychology of why we do what we do. Anyway, that's a side note. Actually, I think the pot should be about these things rather than talking about sales. I don't know. Maybe I'll change the topics to these things, which are more fun and interesting for most people, probably. All right.

Coming into your formative years a little bit, what did you mention? Liberal arts you studied?

Jeff Whitlock: Yeah. So the, my first university was a liberal arts university. And so, you know, just like I said, I, my, my major was technically musical composition, but took a lot of different classes, very interesting classes. Like we took this class called the liberation of sound, which was all about getting sound out of like, basically that music is sort of like constrained and just like, you know, tone, like Western tonalities. And so it was all about listening to very like music that uses different note structures and completely different scales. That was interesting.

And you know, just a lot of different, it's like...

Alper Yurder: What and how it how it moves the human psyche or like how the different sounds give us different.

Jeff Whitlock: It wasn't so much psychological, it was just a music class, but about just like how different, yeah. But it was, but yeah, just took a lot of it. Yeah, it wasn't that fancy, but it was interesting. It was good. And then, I mean, we took classes about like California history and just, you know, this really interesting class about just like, basically just like, you know, I mean, now it's like really, really popular to deconstruct things. But like back when I was, you know, like a kid coming from rural Arizona, I was like, whoa, this is crazy. Like,

Alper Yurder: Okay, fine. Nothing fancy.

Jeff Whitlock: Just kind of deconstructing a lot of things like my understanding of history and society and some core beliefs and stuff. But it was good. It was good to get exposed to that. But I ultimately transferred schools to a very different school, which was not a liberal exposure to BYU, which is a more traditional university, somewhat of a conservative university because it's affiliated with our faith, which is the Church of Jesus Christ of Latter -day Saints. Still had a great experience there. I studied economics, but it was much more like of a practical education, less of like a mind-blowing, question everything, deconstruct everything. Education, yeah. So I got exposure to a little both styles.

Alper Yurder: Okay. Got you. Okay. Well, I'm a little bit going deep is fine, but let's not go that deep. Okay, I get it. Okay, fine. So I'm curious, did you like, from there, how did you end up being the founder that we know you as the persona, the startup founder persona that you are now and this is not your first rodeo, like how the events take you to that direction?

Jeff Whitlock: Yeah.

Yeah, so I graduated, I went to McKinsey and Company for a couple of years doing just management consulting. Had a really interesting experience there. I worked on a variety of different projects. So I did like mining, manufacturing, strategy, just all sorts of random stuff. It's really fun. Two years. Yeah, so just a couple of years. Yeah. No, I think it was good. I mean, I definitely think that...

Alper Yurder: How long you spend at the congee?

OK, great. So it didn't destroy you too much. Good. That's good.

Alper Yurder: I spent six years in consulting, so I did, yeah. I was already destroyed previously, but even more interesting.

Jeff Whitlock: You did. You did. so it did destroy. my goodness. No, just kidding.

That's funny. That's funny. Yeah. I, I liked consulting. It was really great, but, but, I got out of it pretty quickly. And then I did product management, for a couple years. Then I joined a startup as a, as a, as like an early employee. I don't remember like employee number four or five. and then as a head of product. And so I ran product at a, at a startup and this was in Uganda. So this was, I went back to Africa, which was really cool. me and my wife moved there and.

We were working, we were working on this company called safe butter, which is like a motorcycle taxi company. So sort of like Uber for motorcycle taxis in Africa. And that was really awesome experience. Did that until my wife had her, had our first child. And, so she, we got pregnant, she got pregnant in Africa and then carried our baby to term. And then we decided to kind of come back to the States to be closer to family. And, and then that, so I kind of just back, this was like pre remote work. I sometimes wonder like.

You know, if things had happened a few years later, if the company, if I would have stayed with that startup. but back then they were like a fully, you know, co -located company in Uganda. So I, so I had to leave because I, because I had to move. And so that I was already like, wow, I love startups. Like this was such a great experience. I don't really want to go find another corporate job. So let me just try to explore. So I kind of helped my friend out with his startup for about six months, maybe closer, like six, between six to nine months.

But it was under the agreement that I wasn't like fully joining to kind of for the full ride, but I was just kind of like helping him while I explored. And in that experience, I kind of founded, found an idea and a team that I wanted to work with and started on that. That was my first startup called unbird. but yeah, I'll pop, I'll pause there. I've been talking for a while.

Alper Yurder: So those were all B2C, right? Back then.

Jeff Whitlock: Yeah, no, my first startup on Bird was actually B2B, but the first two, my product management experience was B2C and then the ride-sharing startup was B2C also, yeah.

Alper Yurder: Hmm. What the text was.

See, I never did anything B2C in my life. And the closest that I got was B2B2C. How does that experience compare to what you're doing now or for the past few years?

Jeff Whitlock: Hmm. I don't see them as being that different personally. I mean, they're different from like a strategy lens. I think there's a lot and go to market. I think go to market and strategy and sales obviously very different. From a product perspective, they're very similar. And I've always tried to actually bring a B2C lens to my product management, my product leadership. Because, you know, I feel like at the end of the day, you should treat your end users as consumers and they need a good premium experience and...

Alper Yurder: Yeah. Yeah.

I completely agree with that.

Jeff Whitlock: I think that's more common now than it used to be. I think it used to be a bit, you know, there used to be a lot of bad B2B software out there and there still is. Like, has anyone opened up Salesforce? I mean, that's terrible. I mean, so bad. It's just terrible. Like no one loves their, yeah.

Alper Yurder: Yeah. Hahaha.

Just a little in parenthesis. I love how you took a little dig at this giant.

Jeff Whitlock: Anyway, but yeah.

Alper Yurder: Yeah, it's not great. Yes, let's say that.

Jeff Whitlock: So yeah, so I took, so that, that, that the product is, I think product is very similar. It's all about still fundamentally understanding their needs or preferences, delivering great experiences that solves the problems from a, from a distribution perspective. It's, you know, very, obviously very different. buying behavior is very different. Usually in B2C, you just have a single buyer who makes the decision. And sometimes it's more of an impulse buy or an emotional buy. whereas.

That being said, I will say my two B2C experiences were continued. They were basically like SaaS in many ways. I worked at this place called Vivint, which was a smart home company. So basically they would buy different pieces of equipment and then they would pay for upgrades for monitoring and video recording. So it was a recurring business. But still, a lot of times you can...

Initial purchasing decision is usually just driven by one person. And it's like I said, sometimes it's less like, not to say you don't try to deliver value, but a lot of times it's more you're trying to speak, like the jobs framework says there's like functional and emotional jobs. And I feel like consumers a bit more on the emotional side than just functional. It's like maybe 80, 20 or 70, 60, 40, whereas like it kind of flips in B2B. That being said, I still think something that a lot of B2B founders

Alper Yurder: I would definitely challenge you on that. I would definitely challenge you on that and I think it will be a juicy topic to challenge you on that. But I think you were just going to allude to that.

Jeff Whitlock: Well, there might not be that much. Yeah. Yeah, I think there's less disagreement. I was going to say I think a lot of people don't, you know, don't consider emotional jobs as much as they should in B2B. I think it's too functional a lot of times. Yeah.

Alper Yurder: Yeah, it is. I mean, like when the B2B buyer for me, I guess in the last decade of like selling B2B and stuff, there's always like driving emotion, like there's a fear, there's an anxiety. There's like there's a bit of an enthusiasm. I think fear is a very somebody told me one of my very early sales coaches, I think I forgot the second one, but he told me human behavior is driven generally by two emotions like one is fear and the other one.

Jeff Whitlock: Yeah, no, it's true. Yeah.

Alper Yurder: It's something around enthusiasm, I forgot the exact thing, but it's more joyful than fear.

Jeff Whitlock: Okay, that sounds like a lot of wisdom. You gotta remember the second one. But I think I agree if fear is...

Alper Yurder: But I agree with fear because I'm a very I used to be a very fear driven individual in a lot of my decisions. So that resonates a lot with me like risk averse and a lot of buyers when they're buying especially like big deals, you know, every sticker size high. It's a lot of fear.

Jeff Whitlock: Mm. Yeah.

Yeah, no, totally. I think you're totally right. I think at the end of the day, we're human, going back to the thing about we're all humans. I still think though there is a more, it obviously depends on where you're selling the market, but there's a more, a lot, you know, there's still our other, maybe your main champion is a lot of times driven by emotion, but you still need to sort of like check functional boxes or an ROI from other, you know, other parties. So.

Alper Yurder: Yeah, yeah, yeah, yeah. Yeah, you're going to make a beautiful mutual action plan and have all your stakeholders aligned on the shameless plug, which I never do. Maybe I should start and start doing like, you know, every five minutes, a shameless plug of flow into these podcasts. So I want to talk a little bit about the founder experience now that you started mentioning already your current experience there. But it's not your first radio. So how did how did you become an entrepreneur? How did you start your first business?

Jeff Whitlock: Yeah, there we go.

Alper Yurder: …and walk us through maybe briefly through the different things.

Jeff Whitlock: Yeah, so I mentioned how when I came back from this startup in Africa that I joined as an early employee, I decided I wanted to do a business. So I found kind of hooked up with an existing founding team. They were just very early stages. And it was an idea that I really that like I had actually been playing with and they were actually working on the same time. So we're like, hey, let's work together. That was unbird. And that that business was great. Really a lot of fun. It was it was essentially like.

It was a basically, it's interesting. It would have been a different business today with LLMs, but it was essentially like the idea was that we connected to a lot of different data sources and we sold to product product leaders to help them understand the trends in their qualitative data. So we called it like, we called at the time we called it like a feedback analytics or qualitative analytics. So you had like, you had like quantitative product analytics, but then we call it qualitative product analytics. And so.

Yeah, I mean, it was a cool product and we got some good early traction. It ultimately, we went through Techstars with it, which was a lot of fun. But ultimately just had some initial founding team issues. Like we never really could get a founding team to really cohere and deliver at what was needed. So it's hard to say. Sometimes I wonder like if we had just kind of stayed with that idea and then wrote it into the LLM wave. Like, but I don't know, I don't really love that market to be honest. So, you know,

I'm not heartbroken over the fact that I ended up having to stop. So that was the first startup. And then some of that team from that first startup, we actually honestly didn't even fully shut down the company. It was just some of the founders left. And then we just took the existing funding and company and rolled it into the next business we did, which was called Ping Pong. That was a video messaging app. It was actually pre-pandemic. We had...

Unbird was a remote team. We had people in Europe, in Africa, and then US. And we just felt like the tools, like the collaborative tools weren't really geared for that type of team structure at the time. And so we built like an asynchronous video messaging app. So it was kind of like Loom, but more like a messenger. And...

Alper Yurder: Wow. Mm-hmm.

Jeff Whitlock: Yeah, it was really cool. Like you could basically just like have these like asynchronous threaded conversations using screen share and video and voice. And, it was a really cool product and it got a lot of initial traction. Some people really liked it, but then the pandemic hit and then it got even more traction, but eventually, you know, the incumbents started focusing on remote work. And so they built a lot of this like Slack built like their voice note. I don't know if you remember, but pre pandemic, you couldn't even see our voice message through Slack.

Alper Yurder: Mm-hmm.

Jeff Whitlock: So they built their voice notes, they built their video, like where you can share like the video clips. They built like a lot of the huddle feature. So they built a lot of these sort of remote work features into their thing, which really just basically killed their momentum overnight. It was very interesting. And that experience taught me a lot about strategy.

Alper Yurder: Yeah, I was going to say when it killed the world, how did you guys feel? And was it like a atomic bomb dropped in the middle? Or how did that feel? Was it a gradual? You're seeing the momentum drying or?

Jeff Whitlock: It was a gradual seeing the month of dying where it was like before you could kind of feel a little bit of pull, it kind of felt like, there's less pull and we're kind of pushing a bit. And then it's like, even if we're pushing, it's not happening. And then it was, and then, and the thing is that's interesting is like, it's funny how you tell yourself as a founder, like, and I know this is supposed to be about sales, so we probably salespeople do it too. It's like you tell yourself like just so stories, like you like, cause you're always so you're, you're committed on this course of action.

So you tell yourself stories to sort of like make you feel comfortable about your course of action instead of really stepping back and being honest about the truth that you're in. So we would tell, we told.

Alper Yurder: See, that's so funny. I'm the exact opposite. That's the thing. And by the way, it's not about sales, it's about founders, it's about everything. It's about you. So don't worry about having to... But that topic that when you mentioned, you do that, I'm the complete opposite. Like between us as the founding team, I am always the skeptical one, the pessimist one, the realist one. Yeah, but that makes you the founder that you are. And I definitely want to talk about... Sorry, I caught you there, but I was very excited about because...

Jeff Whitlock: Interesting.

Yeah. Yeah. Yeah.

That's good.

Alper Yurder: When you say those things, it's a very founder trait to have. It's a very founder mentality. Fake it till you make it, positivity, because you're basically making a dream happen. So you have to have that kind of mindset.

Jeff Whitlock: Yeah. Yeah.

Right. Yeah, to some degree for sure. But you can also waste time if you don't. So yeah, it's a tricky balance. It's really interesting. Yeah. So like we saw this kind of coming. Like we saw Slack start to message remote working first. And then we're like, well, maybe they're just messaging it. They're not going to build it. And then we saw them drop like their first feature, which I think was huddles. And then we're like, well, you know, for X, Y, and Z reason, it won't be a video first experience and it won't be fully integrated. And it's going to be clunky and.

Alper Yurder: It's a very tricky balance.

Jeff Whitlock: It was all those things, but at the end of the day, it didn't matter because Slack had the distribution and the network effects and it's a multiplayer product. And it's really hard to displace a multiplayer product with network effects. It's almost impossible.

Alper Yurder: Yeah. Okay. What was your role in that founding team?

Jeff Whitlock: I was a CEO.

Alper Yurder: You want to see again? Okay. Look, I've done my research. Sorry. I somehow I missed that.

Jeff Whitlock: Yeah, yeah, yeah. No, it's fine, it's fine. So then what's interesting though, what's interesting is then, so we kind of realized these things, but we still had raised a fair amount of money coming out of Y Combinator. We went through Y Combinator with this business. And so we started looking at a pivot and we explored a bunch of different like hard pivots. Because we like, once we realized like, hey, this business is going to work, we wanted to kind of like keep...

Alper Yurder: Mm-hmm.

Jeff Whitlock: The kernel of what we built, like we didn't want to scrap everything. And so we like looked at different adjacent businesses. Like, for example, like we were like, maybe there's coaching, like asynchronous video coaching. Like, can we sell the coaches like, like sort of, you know, micro coaches who have their own little like, you know, group of people. And we looked at a bunch of things and couldn't get conviction. Everything felt like we were just trying to force a solution into a problem rather than starting with a problem. So we, we kind of like stepped way back and was, we're like, Hey, we just need a pivot. 

And so let's run a very deliberate process to pick a better, you know, a better business, a better market. And we, and we found one that we liked, but you know, as we kind of just going down it, we're like, man, this is going to be another year of building before we can, like we felt we found a problem in a market that we actually really liked. I still think it's a pretty good problem market, but like the need, the MVP needs were just really high. And we were like, man, this is going to be a year of building. And we were already sort of a year and a half into building this other business. 

And so around that time when we were kind of like wavering on whether or not to jump in with two feet into this pivot, that's actually where I was friends with the founder of Grain. And so we actually decided to merge with Grain. So what's really interesting about my startup journey is like, and for better or for worse, it's sort of like just one thing is always sort of molded into the next. It hasn't never been like, I completely failed, shut it down, start over.

Alper Yurder: Yeah, sounds like.

Jeff Whitlock: It's all kind of just been like one journey. So that's been, it's been interesting.

Alper Yurder: So although you are an entrepreneur and a risk taker, I guess you like a bit of safety at the same time. Like it's not like full plunges or maybe I'm misjudging. I don't know.

Jeff Whitlock: No, I think that's fair to say. I think, you know, it's an interesting question. Like I've kind of always just had this like, call it like heuristic or foundational belief of like, I'm just going to move forward, like march forward with the next most available option. I don't know if that's the right approach, you know, maybe it would have been better just to cut.

Alper Yurder: Nice. Survival strategy during Armageddon or something like that. I'm just going to continue to survive like a cockroach a little bit.

Jeff Whitlock: Yeah.

Yeah, yeah, so I mean, yeah, I think in hindsight, in hindsight, it might have been better to just fail outright and start over. But at the same time, I'm happy where I'm at, like grain is going great. It's an awesome product. And, you know, so, yeah.

Alper Yurder: Okay.

Yeah, let's come to that. I mean, it's going pretty well. It's a very crowded market you guys are in, just like, I guess, maybe even worse than us. So let's and we. Yeah, yeah, OK, let's fair enough.

Jeff Whitlock: Yeah, yep.

It probably is worse if I had to say. I think it's more crowded. I think it is.

Alper Yurder: I know that you talk about that too. So let's talk about that a little bit. Like, why do you feel it's too crowded? Let's start from there. Like, isn't the pie big enough for everyone?

Jeff Whitlock: Well, I mean, I don't know if too crowded is the right word, but it's definitely crowded. I feel like if we were better able to differentiate or if we had fewer competitors, we'd be growing more. We're growing fine, but I feel like we would definitely be growing more. My kind of mental model, I don't know if this is right. Obviously, it's very complex, messy reality, but my mental model is like in any space, there's like...

the early adopters, right? You know that whole like, there's like the early adopters and then there's the innovators, early adopters, early majority, late majority. Yeah. I love early adopters. I love them so much with all my heart. They play a very important role. They move society forward, early adopters, man. We wouldn't have startups without them. So, but anyway, like I think that that early adopter group is a lot smaller than the early majority and late majority. And so...

Alper Yurder: Yeah, yeah.

Thank God for them. Thank God for the early adapters, because I'm definitely not one of them and I appreciate them a lot. I love them too.

Exactly.

Jeff Whitlock: If you have a lot of startups kind of going after those same early adopters, it definitely just kind of, you know, can slow things down for everyone in my opinion. So in our space specifically, I mean, the reality is it's kind of an obvious, you know, like Peter Thiel talks about finding secrets. I don't think Grain is a secret. It's just super obvious like that. Hey, you know, business went on calls. There's a lot of value happening in these live calls. We should be recording them.

Now that we're recording them, my gosh, there's AI that we can transcribe and use AI to do automate things with this data and get automatic insights. And so it's kind of obvious. And so I think the fact that it's obvious, it's like, it's a weird combo of like super valuable, but also very obvious. And so, and so I think that combination has kind of given us, has made the market really crowded.

Alper Yurder: Yeah.

It might be obvious, but it's still very valuable. And I don't know if anybody is cracking it. Like there's a few tools which are like, sometimes I'm going into calls and I have like five of them and people are like, what the hell is going on? But I like the innovation that everyone's bringing, like all the automation and how sometimes I envision it to be kind of at the, like a vertical integration with Flowla. Everybody just loves automation and actually let's cut the crap. It's not automation what people love. People just love being lazy. They don't want to do anything.

Jeff Whitlock: Yeah.

Alper Yurder: You know, they just, you know, it's I don't know if it's laziness or they have stolen. Exactly, either way.

Jeff Whitlock: Yeah, yeah.

I think it's people don't want to do boring things, right? It's like, I think a lot of jobs have a lot of boring crap to do. Like for salespeople, for example, it's actually fun, I think. I love talking to a prospect and figuring out what their needs are and trying to solve those needs. I don't love updating my CRM afterwards and going through my task and sending follow -up emails and just all this sort of admin work of sales. It's not that fun. It's boring and most people can do it.

So it's a combination of boring and not using people's creativity and the tip of their skills that only few people can do. It's sort of like a lot of jobs. It's funny because, have you ever read Kalnupur a lot? Are you familiar with him? He wrote Deep Work and a couple other books. Anyway, he makes this really interesting point where he sort of says a lot of knowledge work is, before knowledge work,

like labor used to be divided into a lot of different pieces where it's like, you know, if you're building like a car on an assembly line, you'd have like the people who did the tires and you'd have the people who did the steering and the people who did the engine. And there was like very highly specialized labor. But the interesting thing about knowledge work is like, it's, it's very unspecialized. Like people will typically have like one piece of their job that's specialized and then they do a lot of stuff that's unspecialized, like sending emails, following up, scheduling appointments. Like there's so much garbage that's very not unspecialized and not.

high skilled, to be honest. And whereas like, and like 20 % of their job is high skilled. And so that's what I see is the cool thing about AI is like allowing people to spend more of their time on the high skilled part of their job and less on this like low skilled sort of unspecialized part of their job.

Alper Yurder: Is that how you define also automation? Because everybody throws the word automation here and there, but with your tool, with your life, with the way you build the product, how do you define automation?

Jeff Whitlock: Yeah, I think so. I think you should aim to automate the low-skilled, undifferentiated, unspecialized part of the job. I think there are some startups and some people trying to automate that other piece. And I think it's probably a losing proposition, at least at the time being, who knows, like maybe in a few years. But people want to still do that. Like I still think most people want to do the creative, generative, high-skilled work that they feel excites them, intellectually energizes them.

Alper Yurder: Yeah, yeah, I agree.

Jeff Whitlock: They feel like they're special and they can only do I think people still want to do that. I don't think they want to do this other stuff.

Alper Yurder: I think you very clearly and very simply explained this AI and automation and whatever dilemma, which is nobody wants to do the boring, repetitive, low -skill stuff, but people still enjoy the highly intellectual stimulating, et cetera. And that's leave that to humans, maybe at the moment, at least. I like that definition. I'll steal it. I'll steal it. Okay. So you mentioned already like what you like or not like about sales a little bit, but very like scratching the surface.

Jeff Whitlock: Yeah.

At the moment, we'll see what, yeah, yeah. There we go. Please do, please do.

Alper Yurder: Who's leading the sales effort at Grain at the moment? Is it you or is it somebody you brought into the team?

Jeff Whitlock: It was me up until two months ago. So I was leading the sales effort. Yeah, I'm still involved. I still will do a couple of sales calls a week. I think it's very important as a founder to still be involved. Yeah, critical. Very important data source. So I'm still involved. I still do sales, but we hired a COO who does, who leads our sales.

Alper Yurder: Mmm. good for you!

A COO?

Jeff Whitlock: Yeah, yeah. So, I mean, obviously, you know, the interesting thing about startups is you, you know, I don't know. Yeah. So, yeah. So that was the title. I mean, we could have called him Chief Revenue, but he's also doing some other things. Like he's also leading success. And so, so he, so he leads sort of like sales and success and a couple other like small operational areas. Yeah.

Alper Yurder: I mean, call them whatever you want. I guess they're just spearheading the whole thing. But yeah, it's an elephant in the room. If I don't address that your sales is being left by a chief operating officer, I think that's quite unheard of. But then what does the CEO does is your business. So how did you decide to hand over your. Hmm.

Jeff Whitlock: Yeah. I mean, part of that is, I would say, I would say part of that is because Grain is a product led company primarily. And the majority of our business comes through people signing up using Grain and then running a credit card. And so our motion is more of like a sales assist motion. Not like, it's not the core like driver. It's an, it's like jet fuel or augmentation. So maybe that's why it's maybe with that context, it's a little less odd.

Alper Yurder: Yeah. Yeah. Yeah. Yeah.

You gave me something else to build on. The thing is, my challenge, guys, with this podcast, and I was just telling Jeff this is already 35 minutes into the chat and I'm struggling to keep it in time, but this is going to go on. I think we're having another 45 minutes. So get ready, people. So I have two specific questions for you. One is how did you hand over your baby to someone? How did you decide it was time to move away from you led sales to?

See you all at sales.

Jeff Whitlock: Yeah, I'd say there's there was there's kind of like two things. The first is I feel like we kind of figured out the playbook where it was sort of like we knew how to do it. It was semi repeatable. We I first had other people like so I actually was basically the sales manager. So I asked it's funny. He was he was still the CEO and running other parts of the business. But I said, hey, I want you to be a salesperson. And I want you to start taking, you know, 25 percent of these calls as a rep.

Alper Yurder: Okay. Okay. Okay.

Jeff Whitlock: We also had another couple people taking calls and I was coaching them and being their sales manager. And once I felt like everyone was able to close at a pretty high close rate. Yeah, and we have a very high close rate. It's like 75%, so it's quite high once we get these conversations. And so once it was like, hey, we know how to close at a pretty high rate, I feel like I can delegate this. And then the other thing too was, so is that combined?

Alper Yurder: Mm-hmm.

Wow, that's amazing.

Got you. OK. I wasn't really like hiring a sales guy from scratch. OK, so you had somebody. OK, got you. This makes sense. Yeah. Yeah.

Jeff Whitlock: No, yeah, exactly. Yeah. Yeah. And then the other thing too, was that we realized that because our close rate was so high that like really the bottleneck of the business wasn't converting and closing, it was getting new leads. And so as a CEO, I think, I think your job essentially is to figure out where's the bottleneck to growth and then, you know, laser focus on that and unlock that. So that's why I had to move my focus.

Alper Yurder: Yeah, of course.

Alper Yurder: Especially now that the market is, I mean, we all know it's a bit slower. It's a bit more difficult, like compared to a few years ago. Like, how do you feel the market sentiment is right now? And is there hope?

Jeff Whitlock: Yeah.

Yeah, I think there's definitely hope. I mean, the market sentiment is definitely sluggish. It still feels very sluggish, honestly. People are conservative, the buyings, you know, I think...

Yeah, it's interesting. I think we're still finding growth and we're still going, but people are very cautious to spend money, I think. And they're also taking their existing expenditures and just giving it a lot more scrutiny. So I think before, people would be like, hey, we're not really getting value out of that, but we might in the future, so let's just keep it so we don't have to deal with the hassle of blah, blah, blah, blah. But before, they would just keep it around, and now they're cutting. I see that as a very big difference in the market.

Alper Yurder: Yeah.

Jeff Whitlock: Even in our own team's behavior. We had a lot of tools where it was providing marginal value or like I said, where it was like, hey, we might want to use this in the future when we kind of get our act together. We're not fully utilizing this, but we want to. And so it was like to the point we made about emotion. We had this emotion of FOMO. And so you would kind of keep tools around, but now you're just cutting them. And I think a lot of people are doing that.

Alper Yurder: Yeah, I think retention. It's funny, like we started building Flolo from our own pain points, which is complex sales and the first use case worth closing and enterprise sales and like building stakeholder alignment, all that. But now, for example, the last three, four months, it's been kind of hacked by customer success teams, especially using it for onboarding or retention, nurturing. Like, you know, it's difficult to move through those multiple steps, stakeholders, everything is in one place, blah, blah. It makes sense. Like a mutual action plan.

Jeff Whitlock: Hmm, interesting.

Alper Yurder: or using it as a client portal. So for me, the way I observe that market sentiment is by trying to figure out where can we flow faster, you know? So it's not just sticking to, okay, this was the original plan. It's for the sales guy. Yeah, I know. But now there's a CS person using it. So what do we build on it? So that's how we are not, I wouldn't say pivoting it, but I guess expanding our user base to see where the need is a bit more urgent or, or.

Jeff Whitlock: Right.

Alper Yurder: imminent, where are we going to sell faster basically? Do you observe a similar thing with your product or do you also feel the need to look for other places or figure out where you can sell faster?

Jeff Whitlock: Yeah, I think for us, we actually had the opposite issue is like Grain initially started off as like a very horizontal tool, everything, because we started pre -pandemic. So we kind of got a lot of momentum during the first wave of things coming on Zoom. And so that was great, but it sort of like, I think made us more horizontal, like anyone can record their calls.

Alper Yurder: Everything. Yeah, of course.

Jeff Whitlock: But obviously what's happened over time is like, there's been a lot of competition, enter the market and the existing competitors have grown and stuck around. And then on top of that, like the platforms themselves, like the zoom and the Google meet have added a little bit of like call recording and transcribing functionality. So we actually realized, we actually kind of concluded that this sort of like very generalist, unopinionated call recording space was not someplace we wanted to play. 

And so we've actually like focused, we've actually like focused and narrowed our niche down more into sales specifically as like the point of our spear. We still definitely have a similar thing as you is where like it expands to customer success and product managers and researchers. And so those are still two critical personas for us, but we've niched down and sort of said, Hey, we're focusing on sales, customer success.

Alper Yurder: Niche down.

Mmm.

Yeah.

Jeff Whitlock: sales is the first primary and then the secondary sales and PM at sort of SMB to mid market companies.

Alper Yurder: I told you it makes sense. You know, I guess we came into contact at the point where you were contemplating these things a few months ago. And I'm glad you're moving in the tunnel towards light, let's say.

Jeff Whitlock: Yeah.

Yeah, yeah.

I hope so, I hope so. Let's hope there's light at the end of it.

Alper Yurder: I love that. So in this last section, I'm going to give you a few like keywords or I'm going to do it very like rapid fire questiony type. And I'm looking for like tips, tricks, best practices, strategies for anyone who might be in your shoes or who might be trying to go through a journey similar to yours just to help them out with your wisdom, with your experience. OK.

Jeff Whitlock: Okay.

Okay, yeah, let's do it.

Alper Yurder: All right. So I would say, do you guys am I mistaken in saying were you guys in YC at some point or am I wrong? OK.

Jeff Whitlock: Yeah, yeah, yeah. Grain technically didn't go through YC, but I went through YC with that other company, Ping Pong, that merged with Grain.

Alper Yurder: Okay, so as someone who has that YC experience and I know you share about that too, is it still relevant YC this day and age? Like is it really? How is the YC experience?

Jeff Whitlock: I would say it's not essential, but it's fantastic. I typically still recommend, obviously each case is different, but I still recommend that if you get into YC, you should take a hard look at going. In fact, it's gotten a lot more founder friendly recently. Their terms are fantastic. They give you an uncapped, they invest an uncapped $500 ,000 safe in every business. And that $500 ,000 uncapped safe as just like money in the bank,

in addition to any other fundraising is just really great because it guarantees you the opportunity to work on your business. That being said, if you're a second or third time, yeah, if you're like a second or third time founder and you have existing fundraising relationships and you know you can go raise around on good terms, then maybe it might not make sense. But for first time founders to have access to the knowledge, the community, and then the money on such favorable terms, I think it makes a lot of sense in most cases.

Alper Yurder: Okay, that was going to be my follow up.

Hmm. Hmm.

All right. Great. As you know, now I don't know if this term through entrepreneur, whatever, is it something you like or not? People have different opinions on that. But again, like as somebody who has been through the journey a couple of times, what would you say are your best tips and advice for someone becoming a first time founder?

Jeff Whitlock: Yeah, I'd say my biggest personal learning has been, and I'm not just saying this because of the name of your podcast, but it has been to embrace sales. I think a lot of founders come into the experience as a product person because usually it's the product insight that leads you to want to start the business. You're like, I have this problem and I want to solve it with a product.

And that's great. You know, your product, your product insights are going to be key to building a big business, but you really need to embrace sales from day one. Don't see it as an afterthought. Don't see it as like this, this dirty thing that like commercial thing that like me as a smart engineer or brilliant product person don't need to get my hands dirty with that. It's like, see it as like an essential thing to figure out if you're wasting your time or not. Like, I mean, I literally, like, if I were to do a business and I would, I would put together a pitch deck without any other product and I would just start to sell from day one.

Alper Yurder: Wow, I love that. It touches me very deeply. And so the thing is, in our co -founder group, we're quite lucky that we have the, you know, the builder, the tech guy and the hustler who is me. Yeah, we got the perfect trio. But yeah, always especially my technical co -founder, he should listen to this. I think now as he's been building a sales group for two years and I think now he understands sales is not a dirty word anymore. I love that. OK, what about?

Jeff Whitlock: you've got the... Nice.

Right, that's good.

Alper Yurder: under led sales versus sales expert led sales or someone else led sales. At what point do you hand it over after you check which boxes?

Jeff Whitlock: Yeah, so this is where I have battle scars. I mean, obviously everyone's experience is gonna be different, but we actually hired people to like sales experts. We hired very experienced salespeople from Zoom, which was like an adjacent space. We assumed a very relevant experience. High performer there did not work. I think to me, there's a difference between people who are really good at the craft of selling.

Alper Yurder: Yeah.

Jeff Whitlock: versus really good at figuring out the sales process and the motion at a high level. I think, so again, like we kind of, I feel bad in hindsight, we kind of threw this person to the wolves because we had no idea. We're like, hey, go figure out how to sell. And it just didn't work at all. It wasn't until we figured out, and part of it is like we were setting this person up for failure because outbound doesn't work in our segment.

Even inbound selling wasn't really working. So he was just trying kind of things, but even then he was very slow to iterate. Because he knew his playbook, so he would run his playbook, he ran it for three or four months, it didn't work at all. And then we're like, hey, maybe you should try something else. Whereas I think a founder, I'm not saying salespeople can't be like this, but I think the founding sales set, I think, is to get very early signals and then make pretty good judgments off those signals so that you can iterate quickly rather than run.

Alper Yurder: I think they have a pretty amazing title for that. Founding AE, which I see more and more. Do you think that makes sense? OK. Tell me.

Jeff Whitlock: No, because we did that title. We did that title. Yeah, yeah. I think that works if the AE has been a founder and was a good founder. I don't think you can take an AE and then say, and again, this is different for everyone. There might be a lot of AEs out there who have that kind of, you know, that iterative, generative problem solving ability.

Alper Yurder: Okay.

Jeff Whitlock: But I would just be careful. Being a great AE at an established company does not translate into early stage builder of the sales process, even if you call it a founding AE and frame it that way. We framed it very much that way. We want to give you a founding AE, have you build our sales process. And in hindsight, maybe if I'd managed it more closely, maybe it could have worked a little bit better. But...

Alper Yurder: I think I'm not sure about that. I think it's an intention thing because I think both parties. So you you go into the conversation saying like, OK, I'm going to bring this person with their expertise. And also, I'm tired. I want to hand over a little bit this, you know, tiring thing. And then person is coming like this an adventure. I'm going to be successful, except like good intentions on both sides. But then in the day to day grind, it's hard. You try 55 times and still not working. Then it's difficult.

Jeff Whitlock: Yeah.

Yeah. And I mean, and part of the reason why I really think the founder of the CEO has to be the person to figure out the motion is because our motion involves, we have like, for example, like product triggers. We like, we like, when people do certain things in the product, we say, Hey, would you like to learn more by talking to grain? And like, it's like a combo of like product. We use a lot of life cycle email marketing to sort of entice people. Like I said, we do a sales assist motion. And so a lot of it is, is like sales as a way to like talk to someone to get additional information about the product.

Alper Yurder: Yeah.

Alper Yurder: bring them back.

Jeff Whitlock: And so the actual motion that's worked with us has been like 15, 20 product changes, a bunch of changes to life cycle marketing, a bunch of changes to pricing, a bunch of changes to business model. And then once all those like puzzle pieces are locked in place, it starts working. But like a salesperson can't come in and they don't have the organizational power or the insight to like make all those puzzle pieces that are outside of their expertise aligned. So founder has to do that. A founder has to get that working. And then once it's like, okay, the puzzle is together now here, go and like, you know, go and you know, swim in your lane and build it.

so that's why it has been unsuccessful for us. But, but, but now I think now it's working after, you know, I took the time to actually, you know, go through and make it, you know, make it work, but it was long and painful. And so, so it's always tempting to just kind of like offload it earlier.

Alper Yurder: I think.

Yeah, I mean, we all want to avoid the pain, but I mean, yeah, the times I've done it. And then each time I said, I'm going to hand this over. And then I figured like, no, as the founder, it stops with you. Like you have to figure it out, unfortunately, or fortunately. God, this is such a great conversation. And I've done really terrible job of keeping us to time, but just, just even this makes me think like we should have a PLG versus sales assistant versus sales led or whatever conversation, which I think is a very exciting.

Jeff Whitlock: Yeah.

Yeah. Right.

Alper Yurder: topic to talk about. And now that I'm becoming a bit more of a product person, not just the sales and marketing. And I know a little bit more about those things. And what you just said at the end makes a lot of sense, like the triggers, you know, the behaviors like a salesperson cannot be expected to, you know, build all that motion, especially in a product like yours or mine. Love that. So, Jeff, have I forgotten to ask you anything that I should have?

Jeff Whitlock: Yeah, exactly. Totally.

No, I think this has been awesome conversations. Happy to come back and explore any cul -de -sac we didn't fully go down, but it's been awesome. Yeah.

Alper Yurder: There's too many. There's too many. And it would be an absolute pleasure. It's really great fun to talk with you. I love that how you're you're building something really exciting. You share it very humbly. And I think I think that's that's a very important trait because there's a bit of a founder cult, I think, where people associate being a founder with a bit. You have to be a bit of a cool slash asshole type. I don't know if if that registered with you.

I don't know, I think it's like the big founders who made it. You have to have that type. But the people I speak to are very nice and not assholes at all. So I'm wondering if they're going to make it, not being assholes in this world.

Jeff Whitlock: Yeah, yeah.

I know sometimes I wonder do I need to be a bit more but yeah I know I don't know I will see I think I feel like we're gonna make it but we'll see.

Alper Yurder: Absolutely. Yes, we're going to make it in our own terms. This has been a great conversation, Jeff. That's going to be a wrap on this episode of Sales Therapy. Thank you very much for being with us and sharing your wisdom with our audience today. And yeah, if you enjoy the show, follow us on your favorite podcast platform and any last words from you, Jeff?

Jeff Whitlock: Yes. Go out there and build and sell. Let's do this. We got it.

Alper Yurder: And yeah, and and if one fold. Yes, you can make it without being a jerk. I think and hope so. I actually raised this question and a founder's group of 100 and we were contemplating a few names like who are the people who made it without being a jerk? And there were like, you know, 10, 15 good names that came out. So I think it's possible. Anyway, thanks again. And until next time, thanks for listening to sales therapy. Bye bye.

Jeff Whitlock: You can make it without being a jerk. Bye.