Will Decker of Plug and Play on telling whether the timing is right

Will Decker

Hi Etgar, thank you so much for having me on the podcast, it's a real pleasure to be here.

Will Decker

Yeah, my journey is non-traditional. I studied pure mathematics at Berkeley, and it was very abstract, but I knew I wanted to get into technology and business. My timing was right, I got very lucky to see some critical moments throughout technology and Silicon Valley history. I started in data science, then moved into product management. I was at Yahoo in mobile when the first iPhone dropped, and I got to see the mobile internet go through such a period of hyper growth, it was incredibly inspiring. And I was also within banking and financial services during 2008 and the financial crisis. There, what was fascinating was the different types of behaviors and economics that we saw, that no one could have predicted, and the opportunities that created for large companies and startups.

And then, at Plug and Play I ran the retail and brand practice and started the media ad practice, where hundreds of startups went through the programs. After that, I think what I learned from investing and from growing through enterprise is that I had some superpowers and special insights on very early-stage fundraising. So if you're in the audience and you're in that pre-seed round, that's where I got to see a lot of companies go through that process, what worked, what didn't work. And with the enterprises, I've spent years developing a network of heads of innovation, heads of digital transformation, media and marketing, and what they were looking for, right, not only what types of trends and topics, but also what types of ways that they wanted to work with the outside community, including start...

Will Decker

It's a good question, Etgar. So there are two audiences that they need to really understand and create compelling stories around to become great. One is their investor community, so there's this grind that goes through raising money and raising capital, and it doesn't have to be venture capital, right, venture capital is a great fit for a certain model of company, but there are other resources. As an owner, you own the story of your company, the story of growth and what you're doing now, and how you market that to people who are going to either invest on your cap table or give you a loan or a grant. It's a tremendous amount of work, and the folks who are really great at that can be incredibly successful.

The other audience is your customers, so whether you've got a B2B or B2C business, again, the way you craft your unique selling proposition, the way you go to market, the way you tell the story and differentiate. I think the truer mark of greatness that I've seen is these owners have been able to do that in a way that is simple. They've conveyed the message about who they are, what their company does, and why you should support them and their journey, in a very simple way. The examples that come to my mind are all those cliche catchphrases of the past, someone being the Uber of X or the Google of X. There are different shortcuts around marketing, the messaging, you can do that generate word of mouth, that generate a whole lot of extra benefits for your company, and it's incredibly difficult to do.

Will Decker

There are some pretty key criteria, I think. Number one, and you'll hear about traction a lot, it means a lot, and you'll hear that from the broader investment community, that often times the value that you've created is validated by the number of folks that are using it, now.

05:07 That number, so the traction, which is both the absolute number and the amount that it's growing, is important, because that can be early signals of design partners, so that you're making decisions as an owner and marketer, you're making your decisions based on direct input of the people who will be buying, and that product-market fit. That, for me, where the biggest risk, the business risk in getting involved, is timing, and I'm also speaking as an ex-founder, so I ran a company for a year, and it was great idea, wrong time. Great lesson. So how do you lower that risk as you go through the stages of growth for your company? You're validating through traction. If you're starting to see that traction lift in market, it's a huge piece of that, that is going to lower the levels of risk in terms of product-market fit. So traction's number one, and that would be number of users, or growth of users, active users.

The other important metrics that can play a role, but less important necessarily, is retention rate. You'll get that question a lot, which is: folks come in, you convert, they're using the product, how likely are they to stay with you. I think that might be more relevant later on in growth, because you want to look at, well, do they just have an engine, are these legitimate users, are they really producing value. But I think it's less important very early on, because you're going to break things, right, you're going to get out. I think it's so much more important to get a speed to market and get something that you build into the hands of your customers, that if things are perfect, it is too late.

So they should be breaking, you should be learning, hopefully you have great relationships with those customers so you can build what they want and you can provide value, keep them with you, but I think it's totally okay to get out there early, learn from mistakes, iterate. The other thing that I've seen, that are really standouts, are total dollar and deal size, particularly in the enterprise space. I spent most of my career in enterprise and consumer, and there were some standout companies that went through programs like YC and others, that would have a marketing program centered around building key accounts with enterprises. And so the number of accounts, the strategies they use, and then the ultimate dollar amount of those deals sent them on a completely different trajectory. I think, of course, wouldn't everyone want five, $5 million deals right away, the important thing that I consider though is how you are building and sustaining that momentum, so what's your plan in terms of getting to market, getting there, and then continuing to grow, because you don't want to be in a position a year or two later where now you have stalled on your growth, on your marketing efforts, and that impacts your business, it impacts your financing. So how can you take that long-term view of creating that curve of adoption for your company?

Will Decker

Yeah, that's a great question. The great examples of timing put through a lot of the noise, so you'll get a lot of "no"s, right, you'll get a lot of "no"s from people, whether they're customers, investors. And so what cuts through that and tells you you're in the right time is the end market. So there have been very crowded spaces of lots of solutions, but they didn't have the one solution that would [win]. In fact, the iPhone was a perfect example of that when it came out, right. So there were a lot of devices, in OEM, you know, the mobile market was there, the development market was there, people were using their phones, they were starting to use phones, but it was the combination of the right device at the right market. There, I mean, I was there, and I remember some of the execs at Yahoo saying, "well, it's an okay phone, we'll build an app for that," right. What I think what guided that, in terms of timing, was that consumers were ready, there was a certain amount of adoption and penetration, and it was the right product for them, where combined, at the time, it was music and screen, right, it was the interface and music.

The App Store came later, but it was the right type of product that the consumers loved. The other types of timing you can look at is: if I had the total answer to this, I would be a billionaire, right, I would be in a totally different category. But I think some tips that I've learned are for that early experimentation, and you've had some prior guests on this podcast talk about that. I think the experimentation is key in terms of discovering whether you do have the right timing. Some ways you can get ahead of that is if you have very deep knowledge of the industry, so if you've lived in the job or in the consumer role that is your ideal customer, and you have [unclear @ 10:07], it's a really great indication, particularly if we've seen this happen before, where there's funding behind it, where you actually get approval to go get money to go buy that solution, right, that is a huge indicator, because the one thing is to have this need, it's another thing to go and argue for dollars to go buy something that fits that need.

So if that's successful, that's huge, and what that sometimes leads to is commercialization, you get these internal companies built, they get internal funding, they go get spun out, it's a really good indication of right timing. The other thing is earned media, so if you realize that your early efforts and experimentation start having an over-amplified effect, that's gold. That is incredible. That's where, all you hear about the other metrics like customer acquisition costs and lifetime value, really it's just about that amplified effect of your initial go to market. If you start seeing people telling people, and a great example is, I joined Plug and Play right after they invested in Honey, they were the second investor into Honey, and Ryan Hudson, I got to see him come up on stage, co-founder, and talk about the story of growth, in one of the earlier days. They got very popular on Reddit, a Reddit thread really exploded their company, and you're looking for those moments where it's [unclear @ 11:28] viral growth, word of mouth. You're looking for opportunities where you get out in front of a group, and then that group starts doing the selling for you, and I mean that. If that happens, that's magic, and that is ultimate timing. So you're looking for those types of moments, and if I could predict when those were, maybe that's the next show I'll do.

Will Decker

So the good thing is, everything marketing these days is measurable, most things. I mean, you've looked at a lot of offline attribution, there's a lot of great capabilities around reach and attribution. So the metrics are there, and yes, they don't always have to be truthful, right, but the truth you can [establish]. So the tips that I use when I'm talking to a startup or a marketer: first of all, there's got to be a relationship of trust, right. If you're an owner, if you're a head of marketing and media, and you're looking to work with an investor or an advisor, right, make sure they're going to be part of the team. If they're an investor, there's some negotiation, some natural tension on there, but ultimately they're going to be on the team, got to have some trust. Now what I'll tell you is, things that I'm looking for is, I'm comparing across channels, so it's a bit of a sanity check.

So you've got a product, the consumers, at the end of the day, they're going to be in different segments, they're going to have different profiles, but they're using your product and your service, and the values should be relatively consistent, the value exchange. So there's some natural differences in the cost associated with each channel, that's a really good reality check. So if you're saying that, well, we're advertising on Meta, and we're not spending that much, but we're getting a huge lift from that, but then your search marketing spend is like, if they don't just make sense in terms of alignment to each other, that's a red flag. The other thing is, besides the data, time is the other telling eye. If, over time, there's only so much that you can do to mask those numbers, so that's one thing, time is the ultimate kind of weighing judgment on that, so patience is key.

If I'm looking at it, the other piece though is validating with actual customers, so if you're looking at a story that's a broad picture, while anecdotal, won't be very relevant [alone], to validate with specific customers can be really insightful and give you clues on where to look next, right, so it's again a good indicator to validate where these numbers are real. The other thing is, you can look at industry reports, right, so there's a wealth of information around marketing media, and it's reports both on the activity around spend on platforms, but then also within the competitive set. So if I know the specific company you're working for is within a certain area, of markets, let's say you're in, you know, personalized ad content creation, something like that, you might have a universe of other similar companies doing something related to that field, and so if I get an understanding [of] what their costs are, then that can be a really good... that's a great benchmark for you, right. I think one thing within Silicon Valley, and Silicon Valley by no means has a geographic monopoly on innovation, but what it does have in culture is this open innovation, and so a lot of founders support each other, a lot of the ecosystem supports the growth of these new businesses, and so there's a lot of validation that you can do if you're thinking that your numbers aren't correct, or if you're thinking, well, how do I make sure that people believe this, if you're having conversations with other founders and other folks, they're going to give you a lot of tips and tricks and ammunition as well.

Will Decker

Starting too late. And bet you see this too, you have marketing as a bullet point, or you think that because you're sending some outreach or paid campaigns that you're doing it. Now you've got to spend time really thinking through what's your strategy, plan, what's brand, what's the value prop, what's your strategy to go to market, and then go out there and do it, because if you're not doing your marketing, then you're either lost in the noise, or you're letting the market do the marketing for you. So you've got to own that, and no one's going to tell your story better than you. So understand what it is, be empathetic, right, put yourself in the place of your audience, whether that's your consumers, your business or enterprise customers, your investors, your other stakeholders, and build that message, build that marketing plan. And if you have a marketing background, great. If you can take marketing crash courses, great.

If you have resources like this podcast, fantastic. And even better, get some folks on your team, right, if that's a gap for you around marketing, that should probably be one of your earliest hires, because you're going to be building and selling, and you're going to be fundraising within those areas, marketing is going to support that whole core function. So the most common mistake, as I see, brilliant engineers, they've tackled an incredibly hard problem, they're starting to build some business support, maybe they have a business co-founder, maybe they've got some great investors, but they don't have that marketing person, right, they don't... you can tell, you can tell on the way they communicate, you can tell the way the website's created and positioned, that it's a little bit difficult for folks to kind of get through that, and if you nail it, if you really spend time on marketing and those marketing efforts, it will pay back tenfold in all those different activities.

Will Decker

Well, it's incredibly difficult at that point in time to have one view of your customer. So we have, in the past, there's been great examples of CRM-type startups like [name unclear] and others, that try to reorient the conversation of your customer base with who the customer is, and the way they want to be communicated with. And I think the reason those are so successful is because, as you start to grow up and advance through different stages of growth, you collect fragmented systems, you have fragmented touch points. And so you might be able to be aggressive on your top-line growth, and you might even have some investments in customer success, however, the full suite and the 360-degree view of your customer, anticipating their need, being able to provide proactive solutions, like all that stuff is really hard. It's even really hard for enterprises to do. I've had large enterprise clients, heads of digital, heads of omnichannel, heads of marketing, and they say the one thing I wish I had was a 360 view of my consumer. So that is absolutely the biggest challenge I see.

If you have the opportunity to refactor your view of your consumer, then you can start to be a lot more strategic around your marketing spend and your budget, right, so you get greater dialogue and communication, you get greater strength in how you're going to grow certain segments and engage with certain segments. I think it all comes down to that single view, and so folks who don't have that, I think it's very challenging, and then it's a bit of a guessing game, and you kind of got to rely on talent at that point, so you just get someone in there who's incredibly gifted as a marketer, and how they play that and how they learn that. And then the other [factor] is having a good agency partner, whether or not you need one, right, and the whole agency world is shifting, there's a lot of dynamics happening there, but at the core, if you get a good agency, they're going to be a great partner, they can sometimes provide some of that information and data inside, but they're going to ultimately help you develop the right types of marketing for your brand and your company. Having that, so having the right people and the right talent, having the right view, I think those are often missteps as you start to go down this stage of growth.

Will Decker

Yeah, I got, early on there were a couple folks, really well-funded, raised maybe a hundred million dollars, and went through the program, and I'll just broadly [say], these folks include [names unclear], different companies that had done an extraordinary job of positioning themselves in these new tech markets. There were two things that came to mind as examples. So one was, they were very early stage, they'd just raised a big round, they talked about wanting only five pilot customers, a million dollars each, right, but they really wanted to have these close design partners. It was very clear, it was very simple, their entire message around how they were disrupting the current path to purchase within their field, and what they wanted to do and what they were looking for, and it worked. It totally... and I hadn't seen anything like that up to that point.

A lot of the business models, and a lot of the ask for pilots, was sort of either a talk-call action was closed with later, or it was "here's our SaaS model," but this was very direct, very specific, you look like this, come. It was a slam dunk. I always loved that. The other example that I get impressed with is when you go down vertical marketing messages, so if you have targeted, particularly for enterprise, if you've got a B2B enterprise business, if you are developing vertical go-to-markets and marketing, it can be incredibly powerful. A lot of the enterprises kind of self-segment within their sectors, and so an example within retail, right, could be luxury, could be apparel and fashion, it could be consumer packaged goods, food service, grocery, quick service.

There are all these different components, department and specialty, within an industry, that companies sort of self-align and gather into, and one reason I think that happens is because they see common challenges. So if I have a certain challenge, someone else that looks like me will have that, if they're using this solution I should use this solution. So a super effective example of some marketing, you have very targeted vertical go-to-markets, around everything, right, collateral, content, event marketing, all that story is really tailored to these specific... and then the founders that have been really effective can do that quickly, can see if it hits or not, and if it doesn't, they move to the next segment. And then, boom, so I've had fantastic technology startup companies that I've worked with that could go into any vertical market, but then they maybe start out in media, but then they hit insurtech or insurance, and that's such a smash that they ended up pivoting their entire business to go after that one market. But vertical go-to-market messaging, really good example, and then being novel about where you are at your stage, and what the marketing message they ask is, those are two levers where people have done excellent jobs at.

Will Decker

It's surprising when it really works. It's so hard, it is. I worked with so many different founders that grind and grind and grind, and everyone's got that big vision, but when it finally clicks, it is the most incredible thing, I mean it is just unbelievable. So what I'm talking about is when things start to really take off. I wish it wasn't that surprising, I wish there were many unicorns to be created, but when that does happen, and what I think is interesting is, when that does happen, the founder's reaction, and sometimes there's a lot of fear and anxiety around that success, even early on.

So even early on, you start to get that fit, the marketing takes off, the business, "you were right, you were right, you worked really hard, and things start to take off," like, "whoa, okay, hold on, now I've got so many consumers, or so many enterprise customers," like, "that's a lot of pressure," and, "how do I handle that, how do I deliver against that." Maybe these initial customers are close friends or colleagues or work like... "how do I maintain that trust while I grow, and then how do I look ahead to what's next in the next stage of growth." So when it starts working, I think the biggest surprise within that is the reaction of the founder, and whether they lean in and kind of embrace it, it's like surfing the wave, you go with that, or, how do you let that fear and anxiety kind of navigate your business, and know that you've got a lot of support around you, right, there's a big community you're looking for, it's a great problem to have, that hypergrowth scenario, and I wish, if that's what you want.

Will Decker

Yeah, it's real, it is real, right, but I think it's also very human, and if you go understanding that and that's why founder communities, right, that you're a part of, are hugely important, and paying that forward. So if you've been through that process, Etgar, you've been through that, and the help that you do and the way you [give back] for it, is incredibly powerful for the entrepreneurs to come, because if it's your first time and you're going through that and you need the extra resources or validation, it is there, and it can be really exciting.

Will Decker

Gosh, I think the idea that it's this sort of dream, that "okay, running a successful startup is something that you can just decide to go and do," which is sort of like a Hollywood picture of what being an entrepreneur and founder is, that sort of myth, the, like, where money's just thrown at you and you go out there and you run your own company and you live the dream. Beautiful myth, beautiful dream.

Will Decker

Yeah, right, exactly, yeah, it's just, it's a myth, or [unclear]. Or, I mean, go back to 2000, right, the original dot-com boom, there are these bubbles, and there are moments where that might be true. However, the reality of starting your own company is, it's so hard, there's so many blocks, so you need to have partners to get over those challenges, you need to have support, you need to have the timing align, and all of that. But you also, I think, need to have something special in terms of trying to find [a way to] make it work, like how hard are you going to work to make it work.

I'm not talking about working off-hours through the night, that's sort of an individual choice in terms of how much drive you've got, I'm just talking about how are you going to stick with it and try to find something that works for your business. It's just an incredibly tough job. It's very rewarding, you're your own boss, you are, you know, you're steering your own ship, and you've hopefully got a good group behind you. I also think there's no one path to do that, so there's a lot of playbooks around raising venture capital, and what that path looks like, that is not the only avenue, it's fantastically supportive for high-growth companies, particularly technology, that could then go public, but there are many avenues to building companies. So explore those, be aware of those, learn about those, and see if that's right for you. But yeah, there's more than one way to build a company, and it is very hard work.

Will Decker

Keep following your hunger. It is going to be that curiosity that drives you. And don't be afraid, or, understand it's like a dune, let it flow through you, but understand that fear is natural, and embrace it, find the support where you're going to need it, and follow that hunger. So I think if I were to look back, I think the most I was ever fulfilled and joyful, and in the moments where I found the most success, it was because I was in a place where there were all the things going on, but for me personally, it was something I was deeply hungry to learn about or go do.

That could be a job function, right, there might have been a new area that I wanted to explore, whether it was my first product marketing role, or product management role, building something, like whether it was doing something that was really compelling for me, at the time, for an industry or a space, like now it's a circular economy, what's happening there around food and [agriculture], and around regenerative farming, like there's these different areas and these different challenges out in the space. And I think if I were in those moments and I had those as things driving me, then the rest of the stuff usually clicked, not all the time. Find what your hunger is. The other advice you might hear about, as far as upside and opportunity, is what are the hardest challenges out there right now. So if I'm thinking about starting a company, or if I'm telling my old self, "hey, think about this, what's your hunger," and then, "what are the real tough things out there to solve, that if you solved that, you'd unlock something really cool, right," and then, "if you're not the smartest person that's going to go do that, who is, and go talk to that person." I think those are some of the early pieces of advice, and people are friendly, want to help, so don't be afraid to be the first one to go ask for help.

Will Decker

Well, what are my favorite startups to date, and I'll tell you, I can't choose favorites, but definitely, follow me on LinkedIn, connect with me if you want, I tend to highlight some of the startups and the technologies that I'm working with today, and I choose those ones to work with because I like them, I like their founders, I like the companies that they're building. And other resources and events, what's next, right, so make sure you're following this podcast, I think this is a tremendous resource. Also go out and look at the different events that bring together communities, what types of communities are involved, in the US we have CES, it's the largest gathering of technology that we have, it's a really great community, they have startups from all over the world. There are many others, find that community, get engaged, get involved, and good luck conquering the world.

Will Decker

Thank you so much for having me. Thank you, thank you.