Pouyan:

All right, we're back. I'm Pouyan from Scratchpad and riding shotgun we've got the one and only Ross.

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Ross:

AKA corp bro, AKA corp daddy.

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Pouyan:

AKA the best marketer in the world. Super excited to have Bryan Rosenblatt from Craft Ventures. And full disclosure, Craft led our series A. Bryan, from my understanding you started off in media sales, went to Twitter, then to Reddit and then jumped to a venture firm. So that's a really unique story and unique jump, so why don't we just start there. How'd you make the jump?

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Bryan:

I was working at Reddit building up the sales team in the New York office and on the side was starting to invest in startups. Kept writing these small checks and after a while these small checks added up and my bank account kept going down and I realized I didn't have as much money as I thought I did. And so what I started to do was start SVPs and I started to syndicate deals and go to friends and family and different folks and colleagues and raise money on a deal by deal basis. I realized that's where my energy was going and fortunately someone from Craft, Brian Murray, was looking at AngelList which is where I was running the deals and reached out to introduce and go to know the Craft folks and ended up joining from there.

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Ross:

Yeah, got me hopeful now because I've done that for nine different deals, same thing like small personal checks, brought in friends, family, whatever, people in the network. You've been on the ground obviously, you've been in sales. Do you find that that brings a unique perspective for you or something that gives you a leg up when you're making investments versus a spreadsheet monkey who worked at Bain for two years?

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Bryan:

Yeah, 100%. And you almost don't realize it until you're in the trenches with someone who hasn't done it before. Just the things I think as a sales a person or someone building out a sales team that may come naturally or you've done it for 10 years. A founder that's doing this for the first time, they don't know where to begin. They need to hire their first sales person, they don't know what they're looking for, they're an engineer or a product person.

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Pouyan:

It does make a big difference when you have folks on the other side that have been operators when you're the founder. I think both when things are going well and they're not, there's just a whole different level of energy that comes with it. So there's some folks that will say being a venture investor is basically being in sales, what are your thoughts on that?

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Bryan:

I think there's a lot of truth to it. I don't know if that's controversial or not but one of the things that got me really excited about venture was a lot of the attributes that I think makes a good sales person or sales leader they really do translate to venture. And most people in venture capital they don't come from sales. And so it was a really interesting opportunity I saw where a lot of the things I was really good at were very different than a lot of the things other folks in venture was really good at. And some of the things that they were great at, I was not good at. A sales person that's transactional and just goes through customers, sells the thing and is out the door, that's not going to make a good venture capitalist. But someone who is thinking long term who's listening to their customers who's trying to understand how can I help these guys be successful? That is what I would say is a great sales person and could translate really well into venture.

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Ross:

You were kind of early on the sales team at Reddit, were there any massive moments where you guys were like, "This is it, we're doing it," or big personal wins on your end, closing like the biggest deal? Everything's the biggest deal when it's that early.

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Bryan:

Yeah, there was a couple. One was early on when I joined we closed the biggest deal in the company history then which was a seven figure deal with a huge logo. The biggest deal before that was a tenth of that. But I feel like the most fun part or memory was early on at Reddit we would go and meet a bunch of different brands. We'd meet CPG brands, L'Oreal, different types of folks. And we would meet someone like L'Oreal and they would be like, "I love Reddit, but we're never going to advertise on this website." And a year later, a lot of work, marketing this and that, they're signing up for big deals. And so we started to see this evolution of customers that were like, "No way will our brand ever be on this website," to them chasing us to saying, "we want to be the first one of this category to be on." That was always fun because it was something I think the sales team knew we could do but we were just totally getting shut down early on.

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Ross:

Nobody's posting all their misses on their website. Nobody came to speak to my business school classes about all the horrible investments they made. What have been your biggest fuck ups?

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Bryan:

My biggest mess ups were when I first started making personal investments I did a bunch of them and I sort of in my head was like, "This is my business school, if I lose this money, I lose this money, I'm figuring out if I am good at venture I want to do venture." And so I invested in a lot companies that looking back I shouldn't have, and the main mistake I made was it was an idea that I loved, I was excited about, and I didn't pay enough attention maybe to the team or the competitive environment. I was just so excited to invest in a startup to be able to help the team to put in some money and I was like, "This is going to be great." A lot of those investments, some have worked out really well and some have not and that was the biggest learning is just it's so hard to make a startup work. The team has to be great, the timing has to be right, it can't just be one of these things.

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Pouyan:

Right, but there's a lot of folks that I've talked to that are interested in getting into sales at startups. And there you get one shot, that's your time that you're putting into it. So would love to hear your thoughts for any of those folks listening, how could they go about assessing a startup or an opportunity, say, "hey, is this where I should put years of my time and energy?"

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Bryan:

When I was looking for a new job I met with a lot of people, a lot of companies, so it helped me gage with companies were more prepared versus others and I kind of had a good sense of the risk profile. But I was also very deliberate as far as when I was at CBS I was like, "I want to go work for Twitter." Twitter was something I was using every day, one of the biggest deals I closed when I was at CBS, the reason I closed it and learned about this opportunity was from a tweet. And so I think it's good for folks to just take a step back and think about the companies that interest them and where they want to learn and grow and to just figure out a way to get into that.

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Pouyan:

Any learnings or anything you'd share on folks that are thinking of joining even earlier? Let's see a startup more like series A funded, series B funded and thinking how would I even assess this in terms of investing my time here?

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Bryan:

Get a demo. Like would you buy it if you were your target customers, like really think about that. It's not fun and you're not going to do well trying to sell something you don't believe in. I would talk to potential customers and get their thoughts on the space. I think who your boss is, so maybe it's the founder or a head of sales, is this someone you're going to learn from? In some ways that's even more important is pick the people you're going to work with not just fit the company or the product. It's really hard for people to predict what's going to take off or not, but if you I think align with the right people who are going to teach you and mentor you and that sort of thing, I think that's a good way of assessing whether this is something that's going to work.

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Pouyan:

Can you talk to us about some of the best teaching moments you've had?

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Bryan:

When I was at CBS, we went through an exercise for all of our top accounts and the sales leadership was like, "Write out the org chart." And everyone just wrote their contact at the company and that was kind of eye opening because how many times does a sales person say, "Oh, it's close to closing but they have stuck it with this person or that person or their boss," so just understanding and mapping out the org chart at all of our customers, understanding how they make decisions, who could block it, who could accelerate it. And then based on that, building relationships with those folks.

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Ross:

I want to talk about pitching a little bit because you probably sit in a fair amount of those and obviously that's what sales people do. What are some of the best pitches you've seen? Let's just say for trying to getting investment from you guys. Well, let's start there.

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Bryan:

I think the best pitches are pretty straightforward. It's this is who we are, this is what we're doing, this is why and this is the product. Frankly, there's just a lot of hand waving, there's a lot of big storytelling. Everyone has a vision of being huge, but just trying to understand why you're the right team and this is the right space and just getting into it.

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Pouyan:

So Ross, I know you recently came out of the MBA program, that means washing away some of that MBA speak.

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Ross:

Oh you mean just dropping that doesn't give me money.

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Bryan:

It's like if you guys have ever watched Shark Tank, Mark Cuban always freaks out when someone's like, "If we only get 1% of this audience it's a 10 billion dollar," numbers like that they can be find to look at and understand it's a big market, but when someone's leaning on that and saying all we need is 1% of this huge market and it's great, that's not super, super helpful.

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Ross:

Yeah, I'm trying to think because there's so many folks in sales who want to start something but they're just like, "I have no fucking clue how, like how do I even go about raising money or building a team or even just getting started?" And I think that's obviously a lot of what we talk about here is how do you take that first step. Pouyan, this could even be a better question for you is like, what is that first step? You got your problem, you got an idea, where the hell do people go?

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Pouyan:

To support Bryan's point on cutting the bullshit and just getting to the substance, and this is where I feel like in Silicon Valley so much is celebrated around building and product and it's so easy to spin your wheels and build the wrong thing. Listen, me and my co founder made that mistake, we've been building stuff for nine years. And so what we actually did with Scratchpad early on is before we built anything, we just tried to sell it. We knew we couldn't maybe get the actual dollars or a signed contract but say can we generate any demand? Can we come up? And this is what a lot of SDRs might be doing. Can we write some copy and can we find the right audience and communicate to them, reach out to them such that we just get any signal? Like would any of them be willing to take a meeting with us for this problem?

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Bryan:

Yeah, and that actually brings up a good point. One of the attributes I think of really good sales people, it's not just selling, it's kind of getting feedback relevant for the entire team, product feedback. And so a good salesperson could go in and understand why they're not going to make the upsell or get the client because of what reason and could come back and communicate that clearly to product and leadership and actually change that.

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Pouyan:

One other exercise we did is we just assumed whatever it was we could build it, so then fast forward and say, "Okay, well how are we going to sell it? Who are we going to sell it to? What's our angle? What's our messaging? What's our positioning?" And that's where I feel like those sales skills really can come in valuable. Again, I just feel like maybe a lot of folks don't know that that's a perfectly fine starting point, it's not about building right away.

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Ross:

So it sounds like it's go out there and try to sell the idea to a bunch of people and see that type of feedback you get and possibly make some changes or get the confirmation you're looking for.

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Pouyan:

Exactly, and I think that then supports who is this problem even for? Is the market looking for something like this? Is there a huge gap that everyone else has missed?

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Ross:

There you go folks, go actually do something. Go sell anyway, go keep selling, go sell your own idea.

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Pouyan:

Yes. So just to switch it up though Bryan, one of the things I learned about sales early on was we were hung up on, and we did everything from cold calling to visiting SMBs, going up and down the streets to different stores, and I feel like that resilience honestly has helped a ton as a founder. But how does it feel for you to be on the side being rejected to now on the side of doing a lot more of the rejecting?

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Bryan:

That part is not fun at all and there's a lot there because most of the founders we meet we don't fund. But yeah, I think it's important to develop thick skin and it's not personal. I saw some of the best sales people and senior people and when I did internships with someone who was super successful now, they would talk about getting hung up on or the door slammed in their face, everyone gets rejected.

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Pouyan:

Again, if we go back to the how does sales help with building something or even thinking about building something? There's so much to learn in those rejections if you can get to the why.

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Bryan:

And there's always an opportunity to turn those nos into yeses, like the example I said with Reddit and L'Oreal, they were like laughing us out of the office, a year later they're writing us a big check.

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Ross:

Yeah, the old no doesn't necessarily mean no in sales. If you don't believe that, then you're going to have a hard time selling your product.

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Bryan:

I feel like there's a lead and there's people that are qualified and they say yes and you move onto the next step and then there's the nos, and some of the nos are kind of the see you laters, let's check back in a month, let's wait a little bit for X, Y or Z.

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Ross:

So I have a super pressing question, I think it's probably the one everyone's wondering, is it a prerequisite just to look absolutely fire in your LinkedIn photo to work at Craft? Or is that just a byproduct of working there? Because that brick wall -

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Bryan:

It's a byproduct. Once you accept the job at Craft it just happens.

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Pouyan:

Any big trends you're seeing or anything in "how is sales changing?" I know Craft is really known for investing in bottom up style companies, do you see that being any different in terms of the type of sales person or the type of sales motion to other types like for folks that are thinking about, "Hey, I'm only a year or two into sales, what direction could this go? Where should I invest more time and are other types of companies to look at?"

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Bryan:

Yeah, we're seeing more and more bottom up sales strategies and so when I say bottom up I basically mean customers or prospects are signing up on their own for a product, it could be a pre-trial or a demo or a starter account, and then those leads are being funneled to the sales team who are trying to get them to sign on for a bigger deal, a more enterprise deal. Their biggest challenge is not the lead, it's converting those leads into bigger deals.

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Ross:

Why is it that every time a company takes on Series C they overscale and then fire half their sales team?

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Bryan:

I don't know, that's a good question.

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Ross:

Is it a problem at the top? Is it a problem at the board level? Is it a problem at the investor level? Or is a problem at the CO level? Because it's not a problem at the sales level.

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Bryan:

Before you IPO it's one way, then the company IPOs and they promise certain growth metrics and it goes from the CRO to the VP and all of a sudden you've got a quota and you're looking at it and you're like, "This is not realistic." And I think some companies are smart enough to realize when they messed up and pump the breaks and fix it and others aren't. That's where it gets really unhealthy because the sales people aren't happy and then the company just starts spending like crazy to meet their sales goals so they hire way more sales people than they should who are bringing in more revenue. But yeah, that's what you want to avoid.

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Pouyan:

It's a tough one, there's always this golden age. Like you picked your companies very, very well, you got there right at the beginning of the golden age, product market fits, looking good. But there's all these folks who see these names that are hiring like crazy but the golden era's kind of done and they don't know that. It's like all the reps are hitting but we're hiring 500 people this quarter. That's a red flag, now after my experience, big red flag. I'm not touching a company that's going into that stage because all of a sudden the territories are getting spliced, demand's just going to magically 5X, 10X? The company keeps having the best quarters ever, but the reps keep having the worst quarters ever and the split, like reps start to tail off and companies -

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Bryan:

Yeah, totally. And that sucks for everyone. And then those great sales people leave and they're going to go somewhere else and eventually they're going to crush it at a company and do better and it will work out. But yeah, it's unfortunate because it's a lose-lose for everyone.

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Pouyan:

But if you're a rep and all of a sudden your quota's increased to some unachievable number, what's the right play there?

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Bryan:

Make sure your manager, management, knows where you stand on that. At some point something's got to give and most likely it's not just you who's feeling that, there's going to be other reps feeling that having the same conversations. And when that happens, management's going to have to to something, they can't have every rep missing and being upset unless that's what they do and that's probably a company that's not going up into the right.

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Ross:

I feel like we got to ask our question or our couple questions and the first one is, Bryan what's your go to pump up jam? We're building a playlist of everyone that comes on here, we're getting all the jams. We're going to get your pump up and then we're going to get your sorrow.

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Bryan:

Okay, so pump up jam I'm going to go with Flo Rida, Good Feeling is the name of the song. I don't have a sad song.

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Ross:

You just don't get sad.

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Pouyan:

Really? There's no after you've just been, it's like a punch to the gut and the face at the same time with a deal.

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Bryan:

There's no, when energy's drained from my body I can't even press play on music, I'm on my bed head down, I just don't function.

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Ross:

Just wailing into a pillow.

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Pouyan:

Ross, we'll fill it in, maybe with like a Hans Zimmer soundtrack or something.

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Ross:

Oh, The Wheat from Gladiator. That'll get you jacked up.

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Pouyan:

That'll bring you back.

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Ross:

Bryan, thank you for joining us.

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Bryan:

Thank you guys for having me, this was fun.

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Pouyan:

Yeah, thanks for joining.