Pouyan:

There aren't a lot of folks, I feel like that go from sales to venture.

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Corporate Bro:

Especially from an IC role, like straight up IC work.

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Pouyan:

Yeah, exactly. Typically, it's...

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Cack:

Thanks for the dig there.

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Pouyan:

Okay, the gloves just came off. Let's go.

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Pouyan:

We are back again. I'm Pouyan from Scratchpad, and today we've got Corp with us.

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Corporate Bro:

It's Corp. We're calling it, we're going with Corp today.

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Pouyan:

We're going with Corp. We're super excited to have Cack with us, and there's so much that we're going to unpack together. And your story is... I don't even know the full story, but just the little bits that I've heard is truly incredible. So we're really excited that you're here. Thanks for joining us.

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Cack:

Happy to be here.

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Pouyan:

When did you decide that insight sales was your thing?

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Corporate Bro:

I can guess. History degree.

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Cack:

Actually, yeah. You have a point there. So, I went to Princeton, I did the non-practical, I became a history major, which what do you do with that? I guess you become an academic, but for someone who didn't really love school ever, why I became a history major to become an academic, there's not a lot of logic in that sequence. So, I did run professionally for two years for Nike after college. So that was the equivalent of sort of my I'll go be a ski bum, but maybe with a...

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Corporate Bro:

But with the sickest gear ever.

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Cack:

...what's that?

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Corporate Bro:

With the sickest gear ever. I was a baseball player and we were Nike athletes and all we wanted was just more Nike gear.

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Cack:

Insatiable appetite for Nike gear remains continuous. But no, then I went and I was an investment banker because what do you do when you graduate college? You either go to law school, go to med school, or go work in an investment bank. As far as I was concerned, there was no other career track. And so I worked in investment banking, however, I worked in investment banking in the fall of 2008, which as you recall, the market, Lehman collapsed about two weeks after I started working. So, I did investment banking for a little while and then I realized that investment banking is just sort of an intermediary job where you work on deals.

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Corporate Bro:

It's not super fulfilling and fun.

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Pouyan:

You're shattering the dreams of so many MBA students right now.

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Cack:

You learn Excel, which is a key skill over life. However, your question was why the calling to inside sales. And what I realized was I wanted to go work at a company where the coffee mug was my brand and it stood for something and we made something. Yep, you've got your coffee mug.

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Corporate Bro:

Ready on deck, it's not my branded one. That was a mistake.

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Cack:

I figured I wanted to go work at a really big company because I can apply it to a smaller company. And I wanted to work in a core function. And as we discussed prior, I was ineligible for engineering or product.

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Corporate Bro:

Hard skills mostly.

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Cack:

Marketing didn't resonate. And I didn't know what operations was. And so sales seemed like a perfectly adequate entry-level job. And so at the time, now this was 2009, Oracle was renowned for its sales training.

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Pouyan:

Okay. So you found your way to Oracle, because that was the beacon of sales.

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Corporate Bro:

Pinnacle sales training.

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Cack:

Yeah. And I mean, it was a career, well, nosedive for what some of my college classmates would have considered, all my college classmates were in New York with fancy job titles and I was an inside sales rep. Selling Oracle databases, making, I mean, I won't quote the dollar figures, but insignificant sums of money.

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Pouyan:

At what point did you say, I've had enough of sales.

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Cack:

So I did Oracle for a few years. Then I went to Cloudera, which was sort of the, go work at a startup and appreciate that there are more vendors than just Oracle price list of 14 pages. I wasn't sure I wanted to just rise the ranks of sales.

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Cack:

I would be lying if I didn't also admit that there was some family pressure. I was the deadbeat that didn't have a graduate degree. My sister went to law school and so did my mother and my father. And so there was a little bit of, okay, when you grow up and have a real job, that's probably going to happen after business school. I was familiar with venture capital from working in banking. So, I think I had the secret dream of working in venture, but I didn't really want to let on to anyone because venture jobs are few and far between. So, I didn't really want to broadcast something that I was going to utterly fail at.

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Pouyan:

You decided, okay, maybe venture is the right path. Did you know at that point that venture is just another sales job?

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Cack:

No, with that clarity, I did not.

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Pouyan:

At what point did you realize that? And was that an oh shit moment? Like what did I do? Or was it okay, I got this.

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Cack:

No, that was a oh this is amazing moment.

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Corporate Bro:

Parents aren't mad anymore.

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Cack:

Parents off the back.

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Cack:

No, so I did a summer internship in venture between my first and second years of business school, converted it into a full-time job. So when I started full-time, part of the job of a non-senior person, whatever your title, because there are aplenty. A lot of it is a sourcing job. Sourcing deals, sourcing opportunities and it's combination of that and then through deal execution.

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Corporate Bro:

Did you find that your prospects were more amenable to your calls when you're trying to say, "Hey, we'd love to explore, maybe giving you a few million bucks or whatever." Versus, "Hey, 50K for a Prokka database."

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Pouyan:

Get that budget from them.

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Cack:

That summer that I said that I intern at a venture firm, I actually had two internships. I left at a Friday from a startup internship, which was a walk in the woods. And then I started on Monday at a venture firm and the hit rate on my outbound emails from Friday to Monday, Monday where my email address was @venturefirm.com was 10 out of 10 from zero out of 10 on the Friday before. So yes, it turns out when you're selling money, people generally respond.

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Pouyan:

It's an interesting path because there aren't a lot of folks I feel, that go from sales to venture.

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Corporate Bro:

Especially from an IC role. Like straight from IC.

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Pouyan:

Exactly. Typically it's...

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Cack:

Thanks for the dig there.

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Pouyan:

Okay, the gloves just came off. Let's go.

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Corporate Bro:

Was that a dig? I mean, it's true. I think a lot of sales people-

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Cack:

No it's true.

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Corporate Bro:

They glorify the VC world and they want to get there. And, usually for them to get there, they have to be at some high level where they've done some like personal investing on their own and have to sell their way into that role. So, no, I think that's a jump that a lot of people wish they could make but can't.

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Pouyan:

Obviously, I'm running a company now and I feel I have the very, very fortunate position to have folks involved in as investors that have actually operated before, have sold, have run sales teams. And I can tell you, it is a world of a difference when you're talking to somebody that fundamentally gets it. And there do seem to be more and more companies. I think go-to-market is becoming more important, even earlier in the life cycle of companies. And so I think to have folks that understand that, and have been there before makes such a big difference. At least it does for the founder. I'll be honest, I'm less stressed. I don't feel like I have to educate them on what sales actually means or what go-to-market means.

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Cack:

When marketing became data driven, it elevated its status. I don't know if that was 10 years ago, 20 years ago. Then maybe sales can have its moment. I don't know what the transformation needs to be, but for it to be a more glorified function.

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Corporate Bro:

We're working on it.

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Pouyan:

It's an interesting point because I think in some places sales, like you were saying is still kind of a dirty word, it just has a negative connotation to it.

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Corporate Bro:

I think it would take two and a half million dollars in a writer's room. And let me go make a show about it so that it's no longer Glengarry, Glen Ross, old white guy car sales. It's more Millennial, Gen Z, like people who went to college type sales, which is what it actually is. People literally just don't... They don't know that.

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Pouyan:

Yeah. So, we've got a lot of educating to do. And I think the other fascinating thing, or really interesting thing is the entry point that I think some of the most successful people in sales have is not deliberate. It's not that, I even knew about B2B sales, or I wanted to go do that. It's I really didn't know what else to do. I kind of fell into it. And then I realized, oh, I can be great at... It's like, where I thought I fucked up, I actually didn't. I've landed somewhere where I can apply my skills and honestly make a lot of money-

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Cack:

Make a lot of money.

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Pouyan:

Learn. And so I think approaching it from that perspective would be interesting. And yeah, I don't know when that moment will be. Maybe when as Ross just described as live and it's available on Netflix.

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Corporate Bro:

It's going to happen. I mean, I didn't know I was doing sales at Oracle until day one. Until my first day of Sandler training. Business development, I like to develop some business. I just didn't know what that meant. I didn't know that meant cold calling.

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Pouyan:

Cack, usually we have folks share some pretty crazy stories and I don't know which episodes you've listened to. But in sales, it's generally not hard because there are some interesting stories that come up. So I'd be curious if there's anything you can share. Either from sales and if you can, I would love to open the door on how that then translates into this crazy stories of venture. Because we know there are some crazy stories there, and none of those are really being put out into the open.

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Cack:

I mean, crazy stories. What kind of crazy stories?

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Pouyan:

I think Ross can start.

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Corporate Bro:

There was the guy at Oracle who got fired for expensing his client entertainment at Gold Club in San Francisco. Tried to put like 50 grand in expenses. To be fair, he did close like a multi-million dollar deal. We had a sales manager get fired for duct taping his reps to their chairs and then the phones to their hands. So, they would stop fucking around on the other floors. There was a liquor cart that got pushed on us, it's not that crazy. It was what happened after that, that got weird. But I feel like and maybe you feel like this, Oracle, the nineties was just a different beast than like Oracle in the two-thousands.

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Cack:

They had zero caps on accelerators. They made...

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Corporate Bro:

Yes, the reps were making millions and millions.

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Cack:

Millions, truly millions of dollars. No, crazy from work, no. I mean, crazy to me from Oracle is that some of my colleagues from 2009 are still there.

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Corporate Bro:

That is crazy.

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Cack:

That is mind-boggling.

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Corporate Bro:

Complacency is kind of nice though, sometimes. Why does one leave one venture place to go to another? Is it literally the same exact frigging thing at a new place? You just ideally make more money or have a title change?

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Cack:

We think startups are different. Venture firms are a whole different amount of different. That's not a very good sentence.

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Corporate Bro:

No, but I liked it. So continue, please say more. Because I don't know. I think we need to know, because I don't know.

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Cack:

Venture firms differ obviously in terms of well, venture capital is not one thing, right? Venture as distinct from private equity suggests that venture is one thing. Venture is many things. Venture is pre-seed and seed. And that's high volume and high intuition and a ton of on the ground work, helping founders. Which is distinctly different from late, late stage growth equity or in IVP's case, mid to late stage.

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Cack:

I might need 5 or 10 companies a week, not 25. And our level of engagement with a given company. We just work with a ton fewer companies. So you can give a lot more. Those are completely different jobs. So, venture isn't one thing that's for sure. So firm to firm, you have different fund models, right? You might invest, you have a 100 million dollar fund versus a 2 billion dollar. Those are going to be different. But I think where they really differ is these are partnerships for the most part, not C-corps. So, it's a combination of personalities and the output of a venture firm is decision-making, right? You're just deciding yes or no. Should we spend more time with this company? Should we invest in this company?

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Corporate Bro:

So, heavy ego management is what it sounds like.

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Cack:

I mean, it's a lot of EQ, with a lot of IQ. Theoretically, very bright people are focused on-

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Pouyan:

I love how you qualified it here.

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Cack:

Well, firstly, IVP, everyone's very, very, very bright.

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Corporate Bro:

You can close your door and say that again if you want.

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Pouyan:

We all know the truth, it's cool.

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Cack:

Firm to firm, the dynamics can be very different.

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Pouyan:

I'm thinking about this from the perspective of, if I'm in sales, I don't know much about venture. I work at a company, whatever, we just got some funding. But as you're talking about the fund sizes and stages, is it like SMB versus mid-market versus enterprise?

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Cack:

Yeah. If you overlay startup company land on the venture. Different venture firms, different stages, styles, scales have different product market fit. What is strategy? It's making deliberate choices of what you do and you don't do. Product market for us is not pre-seed, it's not seed, it's not pre-product. We're interested in taking the risk on, can you scale the heck out of your business?

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Pouyan:

So, I wasn't intending on talking much about venture or the investing world on this session. But, just given your experience in the path you've been on. And, combining that with this thread that we've talked about quite a few times. Where, they'll raise a lot of capital, scale the sales team, only to have to let them all go a year or two down the road. What is your take on what the heck is happening right now?

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Cack:

That hasn't been the theme for me, not let's raise a bunch of money, hire a bunch of people and then fire them all because it's not working. Certainly that wouldn't be our suggestion. Back to your prior point of investors opining on what people should do with go-to-market, having never done go-to-market themselves. I try not to give too much advice. But for them, I would generally suggest, let's start small and test a few sales bots before we hire a hundred people.

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Corporate Bro:

No, but I think what you see, it's not so much that you fire 100 reps because they weren't successful. It's that the company still has its best year ever, best quarter ever and all the reps are failing, by metrics of quota. The company from the high level is like, oh great, we're killing it. But, people are not killing it on an individual level. No more sales reps making a million dollars.

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Cack:

Yeah. True. Yeah, and some of that you do see at the board level, because you have the board approved plan, you have the company approved plan and those are different. And, boards for the most part are sort of ruthless and the optimal, they're not actually looking for 100% of quota carriers to hit quota. For them, success is like 55, maybe 60% of quota carriers are hitting quota. So, inherent is that 40% aren't and those-

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Corporate Bro:

But do they even care about the quota? Or do they care about that revenue number? Getting to a certain... Percentage.

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Cack:

I mean, they care about the revenue number. They care that there is enough head count to make up the revenue number. And then depending on the stage and how well the company is doing and they care about the profitability that's been. So, magic number, people care, quick ratio, people care.

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Corporate Bro:

Okay. So I was looking, obviously at your many accomplishments, three time academic, all Ivy, what happened in that fourth year where you didn't get that? Were you going through some stuff? Were you training too much? Parents?

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Cack:

You know...

Corporate Bro:

You only have five athletic records at Princeton.

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Cack:

It's nice that you think it's 3 out of 4. It's probably actually 3 out of 12 because I was a 12 season athlete. So, I would have been in contention for all academic, all ivy, 12 times.

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Corporate Bro:

Okay you run in 12 different ways. Okay.

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Cack:

So I really... It was at 25% hit rate, not 70...

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Corporate Bro:

So, How much do you think, your athletic upbringing translated into sales success? I mean, I think it's a direct correlation.

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Cack:

Yeah, direct. Every ounce of energy I put into sport I think I got out of it and career.

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Corporate Bro:

So, what was your mile time?

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Cack:

Well, we were in the 1500, so it's converted. But my mile time was like...

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Corporate Bro:

Don't do math to me, because I don't know what that means.

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Cack:

4:30, 4:31.

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Corporate Bro:

Yeah that's good. So one of the things we do here as we wrap this up and I feel like you're going to have a good one because you're an athlete and you definitely have a song. So, we do two songs. One is your go-to pump up song, you're in your last lap, very end, what's going to get you there. And then we have your sad song. But let's start with your absolute pump up, huge deal today, or you're competing.

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Cack:

My honest answer would be, listen to Enya.

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Corporate Bro:

I mean, there's something to be said for Enya. Okay. I've listened to that more recently than I like to admit. I don't know why Enya comes up all the time.

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Cack:

So, Enya... Highly pump up. No, I do love me, some Lady Gaga. So, Million Reasons is a favorite these days. My downer music is, probably not listening to music. Just go...

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Corporate Bro:

Sit in silence and stew.

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Cack:

Yeah, be agitated and sad. But then maybe I too would listen to-

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Corporate Bro:

Enya again. Yes Enya again.

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Cack:

She's a constant.

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Corporate Bro:

I appreciate your time. I really appreciate you.

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Cack:

This was fun.