Interview with Author and Renowned Entrepreneur Giff Constable

I had the opportunity to chat with Giff Constable. Giff is a software entrepreneur and maker. Most recently, he was the CEO of Neo, a global product innovation company. He authored Talking to Humans, a book on customer development, which has become required reading in top accelerators and university entrepreneur programs around the world. His skill set merges product management, UX design, front-end development, and sales/marketing.Read on to hear his thoughts on lean startup success regardless of size, getting into the start up scene, qualitative research, reasons to avoid buzzwords, and his favorite food and wine pairing.What was your inspiration for writing Talking to Humans?In 2010, I wrote 12 Tips for Early Customer Development Interviews when asked to mentor at an entrepreneur event. It was one of many things I was talking about, but it turned out to be that slide which everyone was writing down so I wrote a blog post about it. That blog post ended up spreading far and wide.Later, I was having entrepreneurial professors from NYU and Columbia ask me to talk to their classes. One of them said to me, "Look, we use your blog posts, but that's still not enough. We still see our students really struggle with this topic. They sell when they should listen. They're scared on how to get people in. There's just too much confusion. Would you be interested in taking your blog post and expanding it in to something bigger?" I said “sure!” I'm always up for giving back to the community. That was the genesis. I kept it like my kind of business book: short and to the point.How do you recommend companies leverage lean startup methods? Are there any downsides dependent on the size/age/etcetera of a company?That’s a really interesting question actually. It does change as you grow. At the very beginning you are asking some very big questions about your very existence. Once you're past that, you're always evolving and changing, but you don't have to ask those deep questions as to "why?"Lean Startup is about taking a data-informed approach to making decisions in any circumstance of uncertainty – which is most business that I know. The way to success is making the best decision you can as quickly as you can. Let’s learn from the Lean Method, and let's learn from the scientific method. You can't take those things exactly literal since human beings are involved, but everyone can use these concepts to hold themselves accountable.The main reason I like Lean Startup is that it helps me fight against my own cognitive experiences. That's also why Lean Startup is challenging.So yes, in the early stages you have to be asking yourself really hard questions about your whole "raison d'être." Later you can use it just make smarter decisions overall. It's not for the little things either; it's also for the big things. Imagine you're going to make a strategic initiative or are thinking about rolling out a big new feature in the software space. You can run some experiments beforehand to help you figure out if you're heading in the right direction. The good news is that even if you confirm you're in the right direction, you're also going to learn something that is going to make your plans even sharper.It's like customer development or qualitative research. These are something I see a many entrepreneurs start at the beginning, but then they stop. Then the sales person does it, then the customer support person does it, and then it gets pushed off. I think it's a real mistake for people.You never want to stop doing qualitative research, because if you believe in the technology adoption curve, you need to be constantly talking to your customers. Don’t let your product people or your senior people to be totally removed from them through customer support or sales.I will say one thing: when applying Lean methods to a larger company, you must be even more careful about the buzzwords. Big companies go through fads constantly – startups do to, but their lifespans tend to be short. People can have knee-jerk reactions against fads and it's best to focus on the principles and not so much on the language.What advice would you give to other entrepreneurs who are looking to dive head-first into their own startup? My honest answer is be prepared to bootstrap without funding for at least two years.Tell me a bit about the process behind creating Jotto.When I was at Neo (which recently got bought by Pivotal a few weeks ago) I was having a great deal of difficulty keeping everyone pointed in the same direction. We had multiple offices around the world, we had email, we had Slack, but we needed something else to get everybody in sync. I wanted something that was better suited for longer-form content and building community.I love Slack, but Slack and long form don't go well together at all. We tried various tools that were out there but found they're either way too over featured or there are just too many barriers to adoption by a team. So over a few weeks with an engineer, we both worked on building out Jotto together. I did the front end, he did the backend, and we just started using it at Neo. And it worked well.The reason why I kept it as a little side project was to keep taking it forward to see where it went. We don't know yet whether it's a small idea or a big idea, but it's something that's bootstrap-able and we're having fun. It lets me keep my hands in “making mode” rather then “entrepreneur mode,” but I'm not fully ready to go in on a startup 100% right now. We'll see where it goes. We need to invest a little bit in creating the SaaS infrastructure so that people can sign themselves in. We're in the process of doing that right now. I found it really useful for our team and I'm hoping to see sparks fly once we do. What educational preparation would you recommend for someone who wants to advance in your field?It's funny. In some ways I wouldn't necessarily recommend anyone taking my path because I had this crazy-arching path. I think that I'm pretty much un-hirable at this point because from the very beginning, when I first got out of college, I wanted to be an entrepreneur. I apprenticed myself at multiple different jobs to learn as much as I could about many different pieces.I did product marketing, sales, finance, M&A, and product management. As I've gotten older, I've actually gotten deeper in the tech space and deeper in the design side as well. Part of the reason I’ve done this is I love the early stage. When you are starting a new company a general skillset is very, very useful.For later professions and bigger companies, the more specialized you are, the more useful you'll be. The best way to learn in the startup world is to just do it. There's no other way.You could open your eyes to the Lean Startup methodology by doing one of the weekend bootcamps, but everyone I know that has tried Lean isn’t good at it in the beginning. Including me. Your first experiments are 3 months, then you get it down to a week, then you get it down to a day.The same thing goes for entrepreneurship. When I talk to young people who know that they're not quite ready to start their own company but they want to psych themselves up for it, I recommend going to a midsize startup. Don't go to one that's super-super early stage that's like 2-10 people- it could be fun and you're going to have a really great learning curve but it is quite risky because the failure rate at one of those companies is really high. You're also going to be thrown a lot of responsibility and the odds are that it's going to fail so you're going to have something on your very early resume that people won’t recognize.If you go to a 300-person company, then you're likely to be kind of lost and your learning curve might not be quite as impressive either. It's that 50-100-person stage, which is also where I started, that seems to be that sweet spot. Trilogy was the first company I joined. It had 70 people and when I left after a year and a half, it was 200 people. So it had a massive growth curve. That 50 to 100-person stage is really interesting. You still get a lot of responsibility, there's still a lot of growth, but there's a little bit more of a support structure. There's a little bit more mentoring. There's a bigger chance that the brand is going to be worth something. So that's where I say just go jump in to the deep end. Find a startup that you're interested in. Convince them to hire you, and just do it.Do you have any habits that contribute to your success? If so, what are they?The key thing that I’m always trying to do is grow and stay fresh. The danger in technology is as you get older it's very easy to get stale. It'd be super easy for me: I'm a decent manager, I can go get a job, I can manage people - and get further and further removed from the actual work.If being an entrepreneur is what you want to do, when you throw yourself back in to the early stage you have to do the work- and you have to do all the work. Manager, cook, and dishwasher is the joke, but it's true. You have to do everything. So what I try to do is stay fresh so that I can expand my skillset and expand the processes that I play with.Right now I'm reading Christina Wodtke's book on objectives and key results called Radical Focus. I've played with OKRs before, but from a self-accountability and process perspective I like what she's writing about. I'm going to put her stuff in to practice. Right now I'm also trying to learn React so that I could be a little more of a front and back end programmer. Maybe that will help me build my own prototypes.I’m constantly trying to expand the way I think, the skillsets I have, and the technologies I'm playing with. It's easy to stop being a maker, especially as you get older, because you get more senior jobs and you lose your hands on the actual material. You have to kind of force that. One, it's fun. Two, it gives you credibility with the people you're working with who are still makers. And three, it keeps you fresh for if you want to do something yourself.As a food and wine connoisseur, what is your favorite type of cuisine and what variety of wine do you pair it with?Let me put it this way, if there's a peasant somewhere in the world making a dish, I probably will make it too. I love comfort food. I love peasant food, whether it's French, whether it's Mexican, whether it's Vietnamese, Indian. So I do a lot of what is called elevated comfort food. I'd probably braise a pork shoulder with a Côtes du Rhône. All those wines from the Rhône are big, hearty and pair well.Any final thoughts?When people are trying to lead a startup, I see two common mistakes. First they try to cookie-cutter-it or they try to take someone else's playbook at try to apply it to their start up and it doesn't work that way. Your startup is in your context and you have to work your way up from first principles. So think about what's important to you, what you need to test, what your risks are, what your assumptions are, and then what your priorities are, because you can't do everything. I see a lot of people say, "show me the path and I'm going to take that path." No, you have to do the hard work – thinking from the bottom up.The second mistake I frequently see is that some startup leaders get too caught up in data purity. They get really enthusiastic about it and want to do it so zealously and religiously that they end up wasting too much time trying to gather too much data. You can't afford that either as an entrepreneur.You can't have your head totally in the clouds and you can't look for a statistical significance in data purity either. That probably means that you're being too risk-adverse and clinging on to this hope that you're going to get clean and clear data when at early stages, you never get clean data. You always get muddy data and you just have to use your best judgment. The whole point of Lean is that you can have an informed judgment instead of always guessing.