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Navigating startups with Dan Shapiro

40m 44s

Navigating startups with Dan Shapiro

The transcription is an episode of "Beyond the Blue Badge," a podcast featuring Microsoft alumni stories. Host T.A. McCann interviews Dan Shapiro, discussing his entrepreneurial journey, successful Kickstarter campaigns for Glowforge and Robot Turtles, and experiences with investors like Brad Feld. Shapiro reflects on his time at Microsoft, transition to entrepreneurship, challenges in fundraising, and the importance of aligning with investors for long-term success. The conversation emphasizes the need for mentorship, strategic partnerships, and understanding investor expectations throughout the startup journey. Shapiro's candid insights provide valuable lessons for aspiring entrepreneurs navigating the complexities of building and scaling successful companies.

Transcription

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This is Beyond the Blue Badge brought to you by the Microsoft alumni network, where we dive into Microsoft alumni stories that inform and inspire. Hello and welcome to another edition of Beyond the Blue Badge brought to you by the Microsoft alumni network. I am your host, T.A. McCann, I'm the managing director of Pioneer Square Labs, a startup studio and venture capital firm based in Seattle. Prior to joining PSL, I was a serial entrepreneur founding five companies and I spent a little over three years at Microsoft, mostly on the exchange team. With this podcast, I connect with founders and funders that previously worked at Microsoft, attempting to understand their entrepreneurial journey, key decision points along the way, and to extrapolate some key strategy and tactics you can use to build your own successful companies. Today, my guest is Dan Shapiro. I've actually known Dan for many years and he's one of my favorite CEOs. I feel like I always learned something from Dan. In this episode specifically, we're going to talk about building buzz, early interest, and community around his products, as he did with Glowforge and Robot Turtles, both of which were massive successes on Kickstarter. Our shared experience is working with Brad Feld from Foundry, one of our favorite investors. When you decide it's time to sell a company and how he's done that a few times, and using his own experimentation with generative AI to drive new features into his products and to improve his internal business process. I hope you enjoy this time with Dan as much as I did, and now onto the show. Dan, welcome to the show. Thank you so much for having me, T.A. It's a pleasure. You know I'm a massive fanboy. I hope I get to work with you on some kind of company at some point in time. We keep looking company number four. We haven't found it yet, but we will. All right. Take us all the way back to your days at Microsoft. What did you do and on what team did you work? So I am straight out of school. I got an engineering degree from Harvey Mudd, Love Tardware, and somebody told me about this job called Program Manager. And I was like, wait, manager is a direct graduate, and I didn't know what jobs were. I was like, that sounds interesting. And so I went over and interviewed with Chris Jones on the Windows Explorer team and the Windows 98 kernel team, Bob Rini at Lou Perzole's team, and wound up going over to the Windows 98 kernel, where I was working on hardware support for Windows 98 and then rolled off on to ME, which we will soon forget about and Windows 2000 and Windows XP. I wound up working on UI elements and PM stuff like control panel and XP and storage drivers, video drivers, and I bumped around a lot over the five years and got a lot of different experiences along the way. Was there a point in time when you thought, I'm going to be an entrepreneur at some point? Well, so my original plan was actually that I was going to be a patent attorney. I thought that was kind of a cool idea to combine writing that I like to do and arguing and talking and also the technology side. And the path for that as I understood it was you work as an engineer and technology for a while, and then you go back to law school. So I kind of had that idea and I started working on my first patent when I was just a year or two at Microsoft and I was working with a patent attorney and I remember sitting across the table from him going, my job is more fun in this exchange. I'm enjoying the inventing side of things more than I am the documenting side of things. Maybe I'm not on the right track with a patent attorney thing after all. So there was always this notion of maybe I could start a company and do something, but it took a while for me to really realize it. And I was there at Microsoft, well, the whole dot com bubble was happening 98, 99. I was just watching everything get funded. And actually, I'm going to tell you something I talk a lot about. I said this is my fourth company, but really there was a company zero, which I'm not counting, which was in like 99 in 2000. I sat down with a coworker and I was like, we're going to start up and it's going to be amazing. And it's going to be a, you know, multiple worlds and MORPG. And we had no idea what we were doing. None whatsoever. Couldn't get any meetings with anybody spent like six, nine months trying to get the thing funded and then basically just gave up. And it was one of the most depressing professional experiences I ever had. There's a total failure in every way. And I kind of licked my wounds and just did my job for a while and even get back into the whole startup and entrepreneurship thing until a friend recruited me to go join his startup a couple years later. Go back just for a second because I'm such a big believer in side projects. And it sounds like you were doing your day job at Microsoft. You were thinking about the next thing. You're doing this side project trying to get it funded or stood up. Was it in fact the side project? It was. I was pretty deliberate. Like we spent a lot of time on it, put structure together. I took some time off work to go with that in place. But we just had no idea what we were doing. I mean, when I look back, it's not like, oh, we were so close. It's like, oh, we weren't even within a hundred miles of a chance of success. All the resources that we have now, resources like this, resources like so many of the great books that have been written blogs and podcasts just weren't available. And if you are up here in the Pacific Northwest, you didn't have the network of folks who are actually getting stuff done. In fact, the big network was Microsoft. And that startup that I went into was a former colleague from Microsoft who recruited me into a company of all Microsoft alums. Wild seed was the name of the company. And that was my first real experience at a startup and learning how you do a startup for real. What did that feel like to you to want to go to Wild seed? And then your experience at Wild seed going on to now found a company. It was amazing to get to learn all this information about startups and do it on someone else's nickel. So I learned so much at Microsoft. And I'd say like, 75% of it are skills that are essential to being successful. And the other 25% are skills that are counterproductive to being successful and sorting out all the skills and like, oh, how to build and operate a large bureaucracy counterproductive. How to communicate efficiently and get people on board with an idea to bring people along how to inspire an engineering leader with a product vision like all that stuff. Yes, absolutely. And so I got to kind of all sort that out at someone else's startup. And it's one of the things that I recommend highly, which is for folks who are like, I'm thinking about doing a startup, but I'm not quite sure if I want to jump in and lead it myself. It will work for one. Go take a position at somebody's startup and learn on their dime, get to see it from the inside. And that's the cheat code to getting ready to get all that knowledge to go doing yourself. Walk me through from that Wild seed to the idea for the first startup because it happened right after Wild seed. No, no, I took a little detour. So Wild seed, I was there for about three years and the company was sold. There's a lot of untold Dan Shapiro story in here. I feel like it already start up zero the detour. It all just seemed like such a clean line to success where you are today. No, it's so convoluted. And if I may step aside for a moment, one of the things that I find most frustrating about the startup world is the artificially straight line narratives that everybody creates. The 10 years to an overnight success story where the 10 years gets cropped out of the equation. I wrote a book called Hot Seat, the startup CEO guidebook. And it's like eight years old now. But the whole point of me writing it was sort of coming off of my previous startup, having had the experience of like founding and selling a company and writing it down while it was fresh and then sharing like the real dirt of my own experience and the real dirt of other startup founders who were willing to share. So people could see the huge number of failures, the huge number of setbacks. And that every successful entrepreneur on everyone, but most of them have just a huge trail of challenges and disappointment behind them because it's tough going. But to answer your question, after three years, Wild Seed sold, I was actually a part of the last layoff before the company was sold. So I was technically fired. And I'd been looking and like it was it was one of those kind of writing on the wall. And it turned out to be okay. And so I took a job leading the games team at Real Arcade for a year, which I was really excited about because who didn't want to work in games. They're growing up. And so it was a lot of fun. I got to learn a lot about it. I was bit so hard by the startup bug. I wound up continuing to read everything that was available. Probably the thing I've read most religiously was a blog by VC named Brad Felt venture capitalist who was just living his business out loud and was the guy who was opening the curtains to this whole world. And you wrote this book, venture deals be smarter than your lawyer and venture capitalist, which is awesome. And I'd still recommend and refer to it this day. And I was like, someday I want Brad Felt to invest in my company. So partnered up with another friend put together this idea for a company, which was basically cloud sync for feature phones back in the pre-i phone days. I was called on tele. And at the end of a year, stepped out of my role and started pitching at full time. We went all in. And we pitched anyone who would listen to us, pitched everything that would move. Nine months. And we did not raise the first dollar. Brad turned us down very quickly, very politely. It was not, by the way, the last time he would do that. And by the way, spoiler alert, Brad's an investor and go forge my current company, T.A. And I've been working with Brad for years now. But at the time that was someday, I hope to. And for nine months, I could not clear a dime. And as the CEO full time fundraising was my priority one, that was pretty grim. And I remember thinking, if I ever figure out how to do this, if I ever get this done, I'm going to write it down. So I'm not going to keep it a secret. Not going to get keep this. Anybody should be able to raise money. I'm going to say how to do it. And then when it finally happened, when the round finally came together, it was so completely random. And so just like no lesson to be learned, except shrugged that's life sometimes, it was kind of a letdown. What actually wound up happening was this investor who I've been chasing all over Seattle. I was at a conference in Barcelona where I went as sort of a last ditch, trying to drum something up and saw him at a bar and walked up and struck up a conversation and pretended, oh, you're from Seattle. What a small world. Oh my gosh. What do you do? Pretend like I didn't and had no idea. I've been trying to get a hold of him for like three months, schedule meeting. And we scheduled the meeting and he loved the company and he led an investment round and you know, everything came from there. But what's the lesson learned? I don't know. Be sure to head against the wall and try hard for a long time. And it all looks like failure until the moment you're succeeding. Well said. Let's take a slight detour on Brad Feld because we share that and we could spend the rest of the time in Brad Feld, Dan Boy, around I think. Let me tell you what it is that I appreciate so much about Brad as an investor, as a board member and as a friend, so that your listeners may be able to find the Brad for their business and for their field, which really just comes down to like what makes a great VC. So there's a lot of folks who hate venture capital and not without good reason. When I've talked to folks who hate VC or the role of VC, one of the most common reasons for that is because there is a fundamental misalignment of venture capital with their business. And nobody notices it or pays attention to it at the start or may not even be there at the start, but the business grows up in a way that just doesn't work where the founders vision, the direction of the business and the business needs of the VC somehow move out of alignment. And there's a few ways that happen, but the thing that helps you most is by understanding the nature of the problems. You can have those conversations at the very start. So I'll give you a couple of examples. The first and most obvious one is, VCs are there to take a one-in-10 chance of 100-to-one return. They're not really interested in companies that are like steadily profitable, steadily and modestly profitable. They're not really interested in companies that are stable. I'm saying these things like sound good that people would be like, "Why wouldn't you want to come in that was steadily profitable? Why wouldn't you want to come in that was stable?" Eventually, sure, but VCs are interested in investing in companies that are going to take big risks and yield big returns. So if somebody's starting up a restaurant and their goal is to be the best restaurant, they can be that's probably a really poor fit for venture capital investment, probably doesn't meet with their thesis. And that same person says, "I'm going to figure out how to take a restaurant and scale it dramatically, leverage technology to make it one of the most profitable restaurant chains of all time. And here's the plan to do that. Yeah, maybe then that's a better fit." And these things change, right? So you may come in saying, "I'm going to swing for the moon, and then you find this wonderful product and things are going great, and you're growing at a steady 20% per year." And you're like, "I love this." And the VCs like TikTok, that's not what we're here for. We're here to make things grow and make things grow big and fast. And if you're not excited about doing that, then we have to figure something out. We have to replace me, I have to replace you, we have to replace the strategy, like some piece of that doesn't work. That's where I see people really get sideways. Or a company just runs out of growth. And then suddenly the VCs like, "Well, you ran out of growth, I ran out of interest." So understanding from the very start, what your investors see as success, understanding what they see as a fine-base hit and perfectly okay, and the breadth of things that look like failure. Not just the obvious one of bankruptcy, but like what happens if the company doesn't grow for a while. Is that failure? Or is that hang around and we'll keep working on it together? I'm happy to be on the board as long as you need me. Understanding that sort of thing from the start helps you look forward to figure out if this investor is going to be the kind of person who can be a good partner over time. And then there's a lot of things that you just can't anticipate. So your investor moves to another firm and somebody takes over and it's a complete wild card what happens. The firm changes its thesis. Unfortunately in Seattle, we've had a bunch of great firms that have shut down, resized, downsized, changed thesis. Even Founder Group is now not raising another fund, which means that the approach they're taking to investing is going to over the next decade as they continue to run their current funds is going to change. So you can't know that doing your diligence is enough, but you can be pretty sure that if you don't do your diligence, you're going to wind up with an investment partner who isn't going to work for you. So finding that investment partner who loves the business and loves the business, not just the financial forecasts, who is aligned with what you want to do. Whatever that is, the important thing is alignment, not any particular disposition and who works with your working style, whether that is somebody who drives you hard and manages the team carefully closely from a board or somebody who's laissez-faire and sits back and expects you to drive that forward. Are you looking for a mentor? Are you looking for oversight? Are you looking for the money? Understanding what you are looking for will help you find that right person. And so I don't want to say Brad's the best and everybody should have Brad as an investor, even though it's true, because that's not very helpful the most folks. What I want to say is Brad's the best for me and I'm glad to have him as an investor because all those things line up as well as being a decent human, which can sometimes be in short supply and financial community. Yeah, sometimes I build on your thought. I call it many people have heard this phrase called founder idea fit and I've broadened it to call it founder idea investor outcome fit, which is what do we all want from an outcome perspective? Does my outcome align with your outcome? And let's make sure that that is there, which is different than the idea or the founder fit. But they're all inherently related in that sort of sense and that may change over time to your point. May change from when you started the business, whether that's what you wanted as a founder, what they wanted as an investor, what the market wanted from you, what the competitive landscape might have been. So things change over time in a way that you're still looking for founder, idea, investor outcome fit. And in many ways, aligning that on a per round basis. Every time hey, we're going to raise more money, let's reset our expectations on what do we think the right outcome is here for the next 18 to 36 months however long you think that capital is going to last. One other thing I would put into the mix, certainly for my first company, getting mentorship in with my investor base was essential. It was the only reason we had what measure of success we did. And in subsequent companies that took different roles where I was no longer looking for somebody to tell me like what's a fraud and naive valuation. But I still was looking for somebody where I could say what's the latest trend right now in terms of venture financing is in what multiples are there. And this is a reasonable number, you know, as I'm thinking about this chunk of the market how companies like ours being valued. And having the right mix of folks who are ready willing and able to help with that. And who aren't going to take your time up with those conversations is really important. Because if you have a board of let's say five people who all want to talk to about your business all the time, I can wind up taking up a lot of time and energy. You don't necessarily want five mentors. You may want a couple of people who you are close to and can ask all those questions to talk to all the time and a couple of specialists who are like when I have a technology question, this is the person I talk to. When I have a finance question, this is the person I talk to. Yeah, it's such a good point to look around the table and figure what is each board member, what can they really provide. And even then giving them direction on I need this from you and I need that from you. And that also may change over time. Board meeting and board meeting or as the company evolves the role of different board members being helpful to the CEO or the management team. And let me just channel your 2000 Dan at work at Microsoft dreaming of starting something who would say blah, blah, blah, Dan. Yeah, yeah, you know all these VCs, you're talking about it, choose the best one. I just need a couple of dollars to rub together to get this thing started. I can't afford to be choosy. And I just want to validate that as well. It's really hard to fundraise. It's really hard to fundraise when times are good. And it gets exponentially harder when times are bad. Unfortunately, the numbers show it gets exponentially harder when you come for an underrepresented community. If you're a woman, if you're a person of color, it gets exponentially harder. If you're working on something truly novel that's not in the headlines of whatever the hot technology the day is. And I was a white dude in mobile. Like that's playing it on easy mode. And it still took me nine months to get the darn deal done. So I also want to validate that all of our conversation may be a little useless for the person who's going, I can't find anybody. Like I'm not going to worry about finding the right person. I just need to find something. And that's okay too. Like I'm going to find something I'm going to get this going. And I may deal with the wrong investor or terms they don't love because I believe in this idea and I want to have it happen. The end of the day, one of the best predictors of a company's success is the driving determination of the founder. That can make up for a lot of sins on everything else. Damn, before we get too far, let's just tell everybody what glow forge does. So we created the first 3D laser printer, a desktop tool where you can put in materials like wood, leather, paper, fabric, stone, metal, even chocolate. It uses a powerful laser to cut and engrave creations that you can then sell or gift or use in the home, whether it be lamps or wallets or charging stands by a nightstand spice racks. It lets you create amazing and beautiful things at the push of a button. And we now have a whole product line from the glow forge spark at the low end all the way up to the glow forge pro, which is a 45 watt carbon dioxide laser that can cut 20 inches wide by as long as you can imagine that people used to run whole businesses. Okay, let's turn our attention back to when do you sell? You are somebody who's now had multiple exits in your your background. And I'd love to sort of walk through the how and when did you choose to sell the previous companies before we ended up in glow forge land. We were joking before we started about having to believe this. And I was like, don't worry T.A. I'm G rated, but unfortunately, I'm going to tell you a story that well, at least it has one curse word in it. I was tempted to make this the title of my book when I was at Wild Seed, the company that I went to after Microsoft. I was really concerned about something I'd overheard in the one-room. I'd overheard that we were thinking about selling the company. So I very frightened, crawled up the door of our CEO. He was very intimidating, a guy named Eric Thanksgiving's term is wonderful, but terrifying, knocked on the door and he said, what is it? And I came in and I sat down on this bouncy stool because he got these bouncy stools so that people would leave quickly so that they'd be uncomfortable. And then I really liked them and it was really annoyed because the whole point of the stool was to be uncomfortable. I sat on the bouncy stool and I was like, I heard a rumor that our company was for sale. And I just wanted to ask you about that. And he looked at me and said, of course, the company is for sale. The fucking plant is for sale. The price is right. Get out of here. And there was something about that that's very true, which is if you take outside investment, big caveat. If you take outside investment, then you are in some sense saying that your company is going to be for sale, maybe to another company, maybe an IPO, which is a sale to public shareholders. But you are making a commitment that your investors are going to have a return. Generally, investors need to be paid back through somebody buying their shares, whether it's a public market or selling to a company. So you're going to sell your company. You're an IPO, you're going to sell to private company. The ideal is that you sell the company at the point of maximum velocity and maximum risk. So you sell right before the hot product launch that's going to blow up the world or right after the first days of the product launch, when all the marketing is singing in and has all the potential in the world where people look and say, oh my gosh, it's amazing what's going on. And where there's something head that you look at it and go, you know, could go either way. And I'm going to take all the value that I created and all the excitement. And I'm going to harvest that. And I'm going to take all the risk that's around the next corner and I'm going to sell that. And that worked out for me pretty well with Spark Buy, which was comparison shopping for consumer electronics. We built a prototype. We put it out in the world. People thought it was super cool. And then we had to do the hard work of starting to build a consumer user base. Right about that time Microsoft and Google were coming to me saying, hey, what you're doing is pretty cool. We want to use your data feed. Can we license it from you? Can we buy you? Et cetera. Meanwhile, I was looking at the numbers and saying, okay, well, we have a cool product. I've got two Fortune 100 companies who want to buy the data feed underneath. And I could build a business out of that. So I can sell on the excitement of the product we just launched. So we got a great offer from Google, sold the company, investors made money off of it. I got an interesting like resume item and got to work at Google for a couple of years, which is fascinating. And you know, then on to the next startup. I can go just one level deeper. Did you primarily sell from what I'll call an economic perspective or risk perspective or a lack of excitement for the future? Yeah, everything lined up. The company was exactly six months old. So this was brand spanking new. We'd launched the business after three months. We had three months of a close beta under our belt. We could see what was working. We could see what wasn't. And Google was kind of jumping up announcing, let's do this. It turned out they were doing something similarly internal and they got stuck. And they said, your team made enough progress quickly enough. We think you could do this better. If we added you to that team, then we'd be successful. So it all kind of lined up well there. It was a wild time. I will say funding the company, building the company and selling the company all in six months. It was a wild six months. Okay. I've been such a fan of watching how you operate as a CEO. And I feel like every single time I get together with you, I learned something about how you're operating the company. And I'd love for you to sort of talk through maybe just briefly the Glowforge story. A couple of things that you do that are maybe unique to you as a CEO and maybe even some of that sort of co-founder dynamic that you've had through the sort of history of Glowforge. So when we started the company, actually, I'll talk a little bit about the arc at my first company on Tele which became photo bucket. I remember saying to one of the three women in the company, I don't understand why it is that are hiring is so lopsided that we're almost exclusively hiring men. And she was like, oh really? I thought you wanted it that way. And I was like, what? And she's like, well, it just feels like a boys club, not like people are going out doing inappropriate things after work, but like there's remote control cars everywhere and it's paintball and like all the social events are like that. And it just like that was just the vibe I got that I thought you wanted. And I realized that I was pursuing the ostrich theory of equality, which was if I stick my head in the sand and pretend that sexism and racism is into thing, then it'll go away, which doesn't work. And so I just utterly failed it and being any sort of diversity in that company and it really bothered me. My next two companies spark by was tiny. So I never really had enough of a data size to make an issue. And robot turtles was me on a couple of contractors who made a board game and had an amazing year of it. But it was just a small little lovely thing that's still going to the day. I get royalties. It's wonderful. And then when I started Glowforge, I realized I had to get it right. And I say that because what Glowforge does is it builds products that help people create things. And the people who make things in this world do not all look like me. Old white dude. People from all different backgrounds love to create things. And in fact, the best selling maker product in the world, then and now is a company called Cricket that sells to like 90% women. So if we just built a company that looked like the founding team, which was all white guys at the start, things weren't going to work. And I was like, I actually said we're starting ourselves in a white guy hole. We have to dig out of this really fast. So one of our very first priorities was recruiting amazing talent with different backgrounds than ourselves. And really focusing on building a product that would appeal as broadly as possible. And sure enough, at this point, our customers are more than 75% women and we don't have statistics, but real meaningful representation from people of color and various different backgrounds. And it's something that's helped make our company strong. And so figuring out over the while that we needed to do that and then figuring out some pieces of how to do that were really important. One of the things that we learned really early on is that if you are really sincere about building a great supportive environment for folks that are underrepresented, word gets out fast. Not a toxic hellhole turns out to be a really great selling point for a company. And people talk. So if you can build a company that's supportive, if you can build a company that has clear values and lives those values, that's something that word gets out. And suddenly you can hire better people than you could otherwise. Here's our values. Here's our product. Here's what we're about. Then suddenly you're looking at the set of folks who care deeply about you and what you stand for. And it turns out it's much easier to recruit in that world. You don't need every engineer to come work for you. You just need a couple of great ones and you need a reason for them to do that. The same goes true for every other discipline. So it became this really positive feedback loop where it helped recruiting, it helped us build a great team, a great product. And building that into the company culture from the outset was really important. I talked to a few people who work with you and they said you're amazing at delegation. Tell me a little bit more about that. I feel like that might have been lying to you. I say that only because it's one of the areas where I feel like I have the most to learn. I know other CEOs who are so much better at it. I watch and I'm like, other folks, I know who do an incredible job of having everybody come in and say, here's what's going on. I'm going to look at the dashboard. I will help you with the two things you ask for and I'll step out. I have a different perspective on this and I realized it when I was talking to an executive on my team, Marlos Struve, amazing product and marketing executive and she'd just taken over a major new responsibility and she said, you know, Dan, I cut my teeth in the valley and startups in the valley. In the valley, the ultimate sign of success for a CEO is delegate everything. But I get the sense that that might not be the paradigm of CEO that you think about. And I was like, whoa, that's really interesting. I never thought about that. And she said, like, who are your CEO, role models or who do you think of? And while role models, not the right term, the CEOs who I saw operate most closely or at least could see the impact in how they operate were probably bill when I was at Microsoft, Bill and then Steve and then Larry when I was at Google. And there was something about how they operated that stuck with me and very much informs the way that I think about this. And it was probably influenced by my mom a little bit too, if I may take a momentary, momentary side note, my mom is a retired professor of speech and communications. And when I was in school, she was always researching something, running a study, whatever. And I remember around the dinner table, her talking about organizational communications and situational leadership, which was a really powerful notion. The short version is that style of leadership to use isn't a writer wrong. It's a horses for courses. Pick the right style for the circumstance you're in. It depends on the leader, the topic and who you're leading. So with that framework in mind, what I saw back in the heyday was that Bill delegated all the finance stuff. He delegated all the marketing stuff. He delegated all the sales stuff to Steve, but he led from the front when it came to engineering and product. As a young PM a couple of years out of college, I was presenting to Bill and Bill had like my spec in front of him and was grilling me about what it was and asking me her question like he was in there. He was for that moment playing a role that could have been like my immediate boss or like technical mentor at the level of detail and engagement. And he did that all over the company. He led those functions from the front. And during those years, Microsoft was an amazing powerhouse of technology and product. And then Steve took over. Steve led sales from the front and he delegated technology and product. And you know what? In the years Steve led that Microsoft was a powerhouse firm for sales and revenue and finances and maybe not so strong in product and engineering. And I saw the same thing in how Larry led Google. And so that's the model that I think of. There are some pieces of the business where as a CEO, you delegate to those who know way more than you do. And you hire for people who will be the expert and who can educate you. You can keep you up to speed and bring the important questions to you. And in some areas you lead from the front. In some areas, you are the person who sets the strategy and who gets into the details that matter and bring those forward. And you know, I'll say, you know, Bill, Steve and Larry are all folks who have their own quirks and details of their leadership. That was the one thing I saw that was the same for all them. And I seen many other leaders as well. There's one piece of what they do that they are really good at and they work closely with the leadership of their company in that area to lead from the front and they delegate the rest. Yeah. Well said. I have my own memories of the product reviews with Bill and the sales reviews with Steve, both of which were incredibly intimidating for a young product manager that I was experiencing as well. I have them very clear in my mind right now. Some of your listeners may be having mild flashbacks. It's okay. But yeah, then that can evolve with time. A lot of mature companies are led by professional managers who are not leading any area from the front. They're just leading leaders. But that's not what I've seen work, especially at the early days of startups. Dan, we've both been through the startup journey. We know there's lots and lots of up and ups and downs. What do you do to stay even keeled as it were or what advice might you give to other founders to deal with all of those ups and downs? Boy, it's true. And the highs are high and the lows are brutally low. During that startup zero, when that failed, I spent weeks, maybe months sitting on the couch after work, playing video games and kind of being a bump on the log. My then fiance now wife had to stage a bit of an intervention and tell me if I did not quit ever quest bad things were going to happen. Because that was the game I was addicted to. And ever since there's amazing moments and challenging ones, the things that I find personally most useful, my wife's a therapist, so I know like nothing works for everybody. But the things that for me are personally most useful is it helps me a lot to talk to other folks who are going through the journey. I'll hear what they're going through and say, oh yeah, that's actually similar. It's not so bad. I kind of read the news and think about all the stuff going on the world and think how can I help with that and how lucky I am that my worst day is better than the best day of a lot of places in this in these troubled times. And then I look for other things to keep me centered whether it be time with my kids, with my wife, with friends, I'm lucky to have an amazing family. We do stuff together and I can have a terrible day of work and a nice dinner with my wife and the kids and it's a good day. We've mentioned side projects in the past and now you're running a very successful company. Is there another side project happening? I love dabbling and the modern wave of generative AI has been one of the most exciting and empowering things because I'm a terrible coder but now I can make the AI do the coding and I always wish I could do art but now I can have the AI create things for me. And so I have been spending like an hour or two at night multiple days a week dabbling in AI creations. And what I found is I'm like writing these AI side projects and then I wind up with something I'm like, oh, like how for what you could do something from this. And so like some months ago I was playing around with generative AI images and figured out how to really consistently create beautiful images for engraving. And so that turned into a feature that became magic canvas that you know, real engineers with actual coding ability wrote up and shipped that came from that prototype. And I'm working on cooking up some other stuff now which I probably created five things of which four of them just went into the rubbish bin but one of them actually turned into a feature that's now one of our customers top reasons for subscribing to our premium service. And so always reserving a little piece of your time and a little piece of your energy to be creative and to go play. I think yields enormous results. Sometimes it comes back to your day job sometimes it takes you to something new but it is always for me always reinvigorating and always exciting. Okay, the last topic I want to hit with you which you're so good at as well is really bot leadership and I'm not even thought leadership product promotion. I'm not quite sure how to say it but you did so well with robot turtles you've done it so well with Glowforge building community and excitement around your product which you have done incredibly well as a CEO. Tell me about how you think about that, how you do it, how other people might benefit from some of your experience. I'll tell you the one secret weapon that I learned and I figured this out during robot turtles and then proceeded to make my life very difficult by completely ignoring it when I launched Glowforge. It was the one sentence that when any person hears it they either say I'm super excited about what you're doing or cool I'm out. And let me invent a board game with my kids just for fun. It was a board game that was pretty closely based on fundamentals of programming but that was just because I thought it would be an interesting basis for a board game and kind of a neat idea that my kids who are at the time my twins were four couldn't read yet could start following the principles of programming. But I didn't know what to do with it. I was kind of throwing around ideas a friend of mine who's in television asked me to help him pitch a TV show and as we were doing that TV show involve the a crowdfunding element as part of the pitch. And I was thinking about crowdfunding and I was thinking about what makes ideas work and what makes them shine. I got to talk to a bunch of producers of like the voice and the amazing race and hear from them a little bit of what makes ideas click. And I realized that there was this phrase a board game that teaches programming principles to kids as young as preschool that would make 90% of people yawn and 10% of people go ooh I'm in like you don't have to tell me anything else I'm in I'm so excited about that. For context this is 2013 so there were not a ton of STEM toys that were really focused on programming for early learners offline computer learning wasn't a thing everybody thought you had to learn computing on a screen. And so this was novel and even maybe a little heretical that preschool kids would learn programming made some people angry which is great. You want people to react strongly to your ideas. It's much better when it's strongly positive but you want people to react strongly to your ideas. It's much better than ambivalence. It was only when I came up with that phrase that I said I'm going to do something with this because now I have a tool that I can use. A tool that I can use to market effectively a tool that I can use to build momentum and community a tool that will get people excited. Because you know the classic elevator pitch you're trapped with somebody an elevator for 30 seconds what do you say I'm looking at this like how if I have one sentence what do I say and the reason robot turtles worked was because I had a great sentence and honestly the reason glow forage has been amazing but challenging to market is because we never found that sense. It's challenging to say there's this technology that you may think is impossible that's actually possible we developed something like the Star Trek replicator it makes things you push a button it's easy to use everybody says everything's easy to use this is actually easy to use it makes anything you can think of okay everybody says things like that like about blenders no this actually makes like all the thing here let me show you a video like that that was the early pitch and and it's not all that different now you kind of have to see it in order to understand how amazing it is and for me that's so gratifying and it's so fun and that kind of invention and bringing something new into the world is so fulfilling and I do wish there was one sentence that we get people as excited as they did about turtles well there is a great place to leave it Dan and I hope that you will keep working on that one sentence and keep sharing your wisdom with all the founders out there I really appreciate your time today thank you to you thanks for having me thank you for everything you're doing for the startup community into those listening I hope you're inspired and whether you're inspired to take a leap and do something new or inspired to hang tight and let others take the first love risk to join a startup to start a startup whatever it is such an incredible world out there and you know best time to to start something is yesterday and the second best time is today so I hope you have a chance to jump in and take a leap of your own thank you Dan thanks for listening to today's episode if you like what you're hearing be sure to subscribe to the podcast on your favorite podcast app make sure you leave a rating and review and share it with someone you know we hope you join us again for the next episode of Beyond the Blue Batch

Podcast Summary

Key Points:

  1. Introduction to the podcast "Beyond the Blue Badge" by the Microsoft alumni network.
  2. Discussion on entrepreneurial journeys of Microsoft alumni, focusing on Dan Shapiro's experiences.
  3. Insights shared on building buzz, early interest, community, and fundraising for startups.

Summary:

The transcription is an episode of "Beyond the Blue Badge," a podcast featuring Microsoft alumni stories. A. McCann interviews Dan Shapiro, discussing his entrepreneurial journey, successful Kickstarter campaigns for Glowforge and Robot Turtles, and experiences with investors like Brad Feld.

Shapiro reflects on his time at Microsoft, transition to entrepreneurship, challenges in fundraising, and the importance of aligning with investors for long-term success. The conversation emphasizes the need for mentorship, strategic partnerships, and understanding investor expectations throughout the startup journey. Shapiro's candid insights provide valuable lessons for aspiring entrepreneurs navigating the complexities of building and scaling successful companies.

FAQs

To dive into Microsoft alumni stories that inform and inspire.

T.A. McCann, the managing director of Pioneer Square Labs.

Entrepreneurial journeys, key decision points, and strategies for building successful companies.

Originally considering a career as a patent attorney, he shifted focus after enjoying inventing more than documenting.

He recommends gaining startup experience by working at someone else's startup before leading one yourself.

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