Angel Invest Boston is sponsored by Peter Fasse, top life science patent attorney.
Greg Raiz founded app-building colossus Raizlabs and sold it in 2017. He’s now the head of Techstars Boston and has big ideas in mind. Be you founder or angel, listen to this luminous interview for practical advice and inspiration on building startups.
Highlights:
Sal Daher Introduces Greg Raiz, Founder of Raizlabs, the App-building Colossus and Head of Techstars Boston
Founding Story of Raizlabs
“As soon as engineering starts to implement, they learn things, they discover things through the process of implementation that impact the design.”
Steve Job’s Launch of the iPhone Galvanized Greg Raiz to Build Apps for the New Device
RunKeeper Put Raizlabs on the Map, Then Came Rue La La
The importance of Focus on Building a Brand
“I think a lot of early-stage founders, they tried to boil the ocean.”
“Amazon's master plan may have been to dominate e-commerce but in their first several years of Amazon's history, the only thing they did was sell books.”
“Founders really need to think about the long-term growth and trajectory of their business and what elements are okay to outsource.”
Raizlabs Was Sold in 2017, This Intensified Greg’s Angel Investing – Why Raizlabs Ran an Accelerator
Fintech Startup Own Up Grew Out of Raizlabs’ Accelerator and Has Gone on to a Series B Round
Greg Raiz’s Big Ideas for Techstars Boston: (1) Save Lives, (2) Save the Planet and (3) Improve How We Work and Live
Sal’s Story Illustrating How Our Lives Have Improved Since the 1980s
“It's funny we sometimes don't reflect on how fast society and technology can change the day-to-day of interactions.”
Techstars Boston Is Leaning into the Coming Decade of Biotech
“I think biotech and medical specifically, Boston has one of the hottest markets, if not the hottest markets for many of those technologies.”
“...we have an incredible Fintech sector. We have an incredible robotic sector. We have incredible 3D printing sector...”
Sal Daher Talks About One of the Big Differences between Biotech Investing and Software Investing
Sal Daher Expresses a Need to Train Angels in Biotech Investing
“I want to accelerate companies that are really important and meaningful and I expect to get a capital return to allow me to do more of that.”
Check Out Greg Raiz’s YouTube Channel – Half Ideas
What Are Half Ideas?
YouTube Is the Number 2 Search Engine
It’s Hard to View or Listen to One’s Early Content
How Greg Raiz Discovered Computer Programming
The Vast Horizons of Software
How Bad User Interfaces Create Inequality
PURE GOLD: Greg Raiz’s Parting Advice to Angels & Founders
Transcript of, “Big Ideas at Techstars Boston”
GUEST: Founder and superangel Greg Raiz
Sal Daher: This podcast is brought to you by Peter Fasse, patent attorney at Fish & Richardson.
Welcome to Angel Invest Boston, conversations with Boston's most interesting founders and angels. Today, we are really excited to be hosting with us founder, angel investor, and head of Techstars Boston, Greg Raiz. Greg, welcome.
Greg Raiz: Thank you so much. Really excited to be here. It's just fantastic to be at the intersection of all of those exciting things.
Sal Daher Introduces Greg Raiz, Founder of Raizlabs, the App-building Colossus and Head of Techstars Boston
Sal Daher: Greg was the founder of the eponymous Raizlabs, which if you remember, just half a decade ago, if you were building an app, if you didn't build your app at Raizlabs, you didn't have an app. Tremendous. Greg is a colleague of mine, also at Walnut Ventures, I'm very proud to say, and an excellent contributor. Welcome again.
Greg Raiz: Thank you so much. It's just been a fantastic journey, both starting with some of the mobile development and learning how to be a CEO and learning how to grow business, to ultimately exiting that business and starting to angel invest and work with so many early-stage founders in the Boston area. It's just such a great community, and I've loved becoming part of it and giving back to the city that gave me so much.
Founding Story of Raizlabs
Sal Daher: Oh, excellent. People like founding stories. Tell us the founding story of Raizlabs, how did that come about?
Greg Raiz: My first job out of college was actually working at Microsoft. I went to school in the Boston area, Tufts University, and started working at Microsoft. When I left Microsoft, I really didn't know what I wanted to do. There's a number of things that I was exploring, from technology and design and software. My true passion is really making complex things simple. I like to say that, that really lies in the intersection of technology, which is my background and education of computer science, and design and human factors. Ultimately, you can have the most technically amazing artificial intelligence whiz-bang thing, but if humans can't use it, it doesn't matter.
The early days of Raizlabs was really just me in a coffee shop. I would literally go to Coolidge Corner and either sit in Starbucks or in Peet's coffee, and I would work on designs and software. We were really doing that for a bunch of different companies, but I didn't know anything about business. I would literally try to figure stuff out and I would go to the library and read books on stuff. It took me a number of years, but I started to get a little bit of the flywheel all going. We're doing a lot of websites, a lot of usability.
I actually got very involved in the user experience community in Boston. I was on the board of UPA, which is the Usability Professionals Association, and I was on the board of BostonCHI, which is the computer-human interaction society. Ultimately, it was like, "How do you make software easier to use?" We would design these products, these software applications, and ultimately, we would hand them off to an engineering team. We'd check in a couple months later, and be like, "Hey, how's it going?" Everything was sideways. This happened over and over again. I was like, "What is going on?"
“As soon as engineering starts to implement, they learn things, they discover things through the process of implementation that impact the design.”
At first, I was like, "Well, they're just bad engineers," and that's actually not the case. There are fantastic engineers, but design, as I learned does not end when the design initial screens are done. As soon as engineering starts to implement, they learn things, they discover things through the process of implementation that impact the design. I started thinking, "Well, how does engineering and design work better together?" We started to A, hire our own engineers, and outline this methodology of design and technology being built together, that way, you could iterate in an agile fashion. We were really lucky. We were in the right place at the right time with that philosophy of design and technology.
Steve Job’s Launch of the iPhone Galvanized Greg Raiz to Build Apps for the New Device
When Steve Jobs stood up on stage and said, "This is the new device," and when he unveiled the iPhone, we were like, "Oh, that's pretty cool." That's a device that appreciates the elements of design and simplicity user experience, a lot of the things that we were already talking about, and it requires new technology. One of the things that we discovered is that, especially large companies have a hard time rethinking technology, especially if they have a lot of technical debt or a big enterprise application. Here was this mobile device where there was no apps, there was no software and there was this need for software and technology.
RunKeeper Put Raizlabs on the Map, Then Came Rue La La
We really started with that philosophy of technology design fuse together, and because there were not a lot, maybe a handful of service providers at the early stages doing mobile app development, we were really able to get a lot of traction initially. RunKeeper was one of our first apps launched into the App Store. It was actually launched under the Raizlabs brand before we actually transferred it over to our client, FitnessKeeper. Obviously, that company went on to be super successful and Jason's done amazing things but that led to other companies, certainly in the greater Boston area, saying like, "That's cool. Who did that? Who's working with you on the app?"
That led to us working with Rue La La on their mobile applications and Care.com, and a number of other Boston area companies. Over time, we cornered the Boston scene and gained reputation here, and started working with national brands like Macy's and Bloomingdale's and Costco and Six Flags and so many others. The company still, we got acquired in 2017 but a lot of my team is still doing amazing work over at Rightpoint right now.
Sal Daher: Excellent. Curious, we were talking before, you have great experience building a niche for your company. Would you care to talk about that? How you approach that?
The importance of Focus on Building a Brand
Greg Raiz: Yes. I think to some extent, it was accidentally discovering this but it's definitely something I recommend to founders at this point. People told me to focus. They're like, "Hey, you need to focus." I was like, "I don't know what that really means because my background was building technology and thinking about design." Initially, when we would talk to customers or clients would be like, "Oh, we can do usability and design and wireframing and software development and engineering and all of these things."
I think it became difficult for people to reference and refer and say, "Oh, Greg is best at X," because I was diluting the messaging. When we focused 100% on mobile, our marketing became easier. I think our second-degree and third-degree connections, it was easier for them to articulate who we were and what we did. It's tricky because I think founders think they're pigeonholing themselves by niching. They're like, "Well, I don't want people to think that I can only do mobile." It's interesting because the opposite ends up being true. Once people know how to communicate about you, then they can ask questions, "Oh, I see you do mobile, can you also do X?"
“I think a lot of early-stage founders, they tried to boil the ocean.”
We were actually able to grow our collective pie or collective share of the market by being really focused. I think a lot of early-stage founders, they tried to boil the ocean. One of the things I talk a little bit about to founders is what I call the master plan. Amazon's master plan may have been to dominate e-commerce but in their first several years of Amazon's history, the only thing they did was sell books. That was it. Because they only sold books, it made their messaging easier, "Oh, you need to buy a book, you can either go to a physical bookstore or you can go buy a book."
“Amazon's master plan may have been to dominate e-commerce but in their first several years of Amazon's history, the only thing they did was sell books.”
Once they had the book space dominated, they were like, 'We're just about books." Then they're like, 'Well, maybe books and music. That's it." Then they slowly kind of grow and grow and all of a sudden, you're buying lawn mowers and toothpaste on there. It took them a decade to get there. I think for founders, they try to go too far too fast rather than niching down and getting really good at whatever their niche should be.
Sal Daher: Very true. The point you were making about the interaction of design and engineering going back and forth, I've been reading some stuff recently about US manufacturing. How the US manufacturing base has, a lot of it has gone overseas and with it the capacity to design a lot of new products because a lot of design is tied to how you build things. Somebody creates a design and if you have to fly around the world to see how it's being implemented, it's a lot harder than if you are designing and the factory is just down the street. That's a point that people think you could just abstract away. The world is highly imperfect.
You design something but once it gets implemented, you have to go back and figure out, "Oh, yes, forgot about this." You got to think about that. It doesn't work quite like we expected.
Greg Raiz: That's absolutely true certainly with hardware products but really products across the board like software is never effectively done because it's always dealing with the human element. Humans tend to want more. If you build a feature or a product that does X, we want X plus one. Oh, it does this thing. Can it do a little bit more? The same is true about physical hardware products as well or really even manufactured goods do a lot of stuff in medical devices or medical products as well. We talk about whether it's vaccines or antibodies or software or B2B SaaS or Greentech or whatever, there's always iteration.
“Founders really need to think about the long-term growth and trajectory of their business and what elements are okay to outsource.”
Founders really need to think about the long-term growth and trajectory of their business and what elements are okay to outsource. I don't suggest that every entrepreneur will try to do everything, but what are the things that are going to create long-term value and lift for your business in need rapid iteration. Again, there are certain places in the world that have the infrastructure to iterate more rapidly, but that obviously has impacts on supply chain and other things like that. As an entrepreneur, you're always thinking like, "How do I balance speed versus redundancy versus taking on dependencies?"
When I was at Microsoft it was very much a, we don't like to take on dependencies as a company, because that means that someone outside of the business can control our potential success or failure. I think that's a very black and white view of it. As an early-stage founder, you have to weigh all those pros and cons for every decision that you're making.
Sal Daher: How did you get into angel investing?
Raizlabs Was Sold in 2017, This Intensified Greg’s Angel Investing – Why Raizlabs Ran an Accelerator
Greg Raiz: I sold my business in late 2017, but even prior to selling my business, one of the things I'd done even while running Raizlabs is I ran an incubator. One of the things that happened in our business as we grew from working on very early-stage small companies and startups to working on massive Fortune 500 clients and companies, we lost the ability to be able to do some of that early-stage work. It was a lot of fun because some of the early-stage work is incredibly collaborative and incredibly fast. When you're working with a Fortune 500 company, all your timelines and deadlines are six months or a year or two years out.
There's a lot of iteration because you're working with massive global companies that require a lot of checks and balances, a lot of signatures, a lot of approvals. When you're working with a small startup team, you're working with a founder they get to greenlight things. They say yes or no. If something works you can rapidly iterate and get a product out to market in weeks and months if you're doing it correctly. In late stages of Raizlabs, we moved into a large office space, and we wanted to get more in touch with the startup community just because we had started to drift more to these large corporate companies.
We ran two incubator classes where we weren't investing capital, but we were investing our time and resources to look at their products to advise them, to help them, and to see where they're going. One of those companies actually went on to raise capital. They actually recently raised their B round. That introduced me to some of the elements of angel investing,
Sal Daher: Would you care to mention that company.
Fintech Startup Own Up Grew Out of Raizlabs’ Accelerator and Has Gone on to a Series B Round
Greg Raiz: Yes. That company is called Own Up. Great Boston company, great founders, they're doing mortgages and mortgage refinancing, and all sorts of interesting tech around there, but when they started in our incubator, it was literally two guys with an idea. They were like, "Hey, we been in this space. We think there's an opportunity, we haven't even incorporated at our company, but we think there's something there." I liked the founders. I was like, "Sure, let's go through this."
That incubator was really them putting in. We had a number of companies go through that, putting their companies together, understanding the basic mechanics of business. Me coaching them on how to hire engineers, how to think about their product, how to think about pitching investors. There is just a lot of fun to vicariously live through other company's growth as success. I did end up angel investing in them, number of other companies as well, but that gave me a taste that I was like, "Oh, that's a lot of fun."
When my company had an exit event in 2017, I ended up selling the business. It put me in a fortunate position where I could continue to do more angel investing and advising. I started doing more in 2017 and when the pandemic came around and I parted ways with my acquiring company. It's like, "Hey, I can spend a lot more time and a lot more capital getting deeply involved in the Boston angel community and mentoring a lot more startups and companies."
Sal Daher: Awesome. Would you care to talk about some of the other angel companies that you're involved with?
Greg Raiz: I love all my startups. There's just a bunch of great companies. Maybe rather than talking about any specific one, I'm really tracking and interested in helping founders that are having a profound impact on humanity. That was actually one of the reasons why I specifically wanted to join Techstars. I started to look at my own investments and the reasons why I was investing. There's obviously the capital return.
Like I want to make money through my investments, but then I started to ask the question, "Okay, beyond capital return which was an angel is certainly important. It gives you flexibility to invest in more companies. What do I really want? What kind of change and impact do I want to have in the world?" I started to develop my own thesis around both angel investing and advising and specifically for Techstars, I'm looking to advance the elements of humanity.
Greg Raiz’s Big Ideas for Techstars Boston: (1) Save Lives, (2) Save the Planet and (3) Improve How We Work and Live
There's three pillars for me in 2021 that I'm particularly focused on. The first is, how can we accelerate companies that save lives? I think saving lives in particular, there's a number of different technical and technology fields, both med-tech, med-devices, biotech, pharma, emergency management, other things in that space that-- There's just so much opportunity to build amazing companies and products and that, to me, feels like something worthy of accelerating as an angel investor or as a Techstars investor.
The second pillar for me is really how do we save the planet. There's so many things that impact our daily lives in terms of health and wellbeing, from the quality of our air, the quality of our water, climate change, things of that nature. Again, there's so many different technology areas that are particularly interesting there, whether it's EVs and batteries and solar or filtration and water and air to all sorts of other interesting innovations in material science and technologies.
The third is how do we profoundly change the way we live and work? We end up spending a lot of time in front of screens and computers and phones, and because I'm a user experience junkie, I'm not satisfied with the status quo. I want to accelerate companies that are really thinking about how do you change the human experience, either at work or at home, and there's a lot of opportunities of inefficiencies or things that could be of dramatic impact to life and wellbeing. I'm looking for companies that are really thinking differently and trying to take that and put it on its head.
Sal’s Story Illustrating How Our Lives Have Improved Since the 1980s
Sal Daher: It's funny your third category, how people work and how they live. You're a young guy, Greg, let me just illustrate for you. The late 1980s, I was on a business trip to New York. My uncle was picking up my wife and little daughter who was three years old at the airport, and there was confusion about the terminal where they were and so forth. It ended up that because we didn't have cell phones in those days, a few people had pagers, my uncle ended up calling my boss whose husband was from a family of concentration camp survivors so when he hears someone is missing, he goes into panic mode it's like, a missing family member. He revs up.
Somehow my uncle found out that I was also in New York, calls me, and then finally, I can tell him where they are, but this is like three hours of agony. Young wife and a three-year-old, lost at Logan and my uncle couldn't find them. This doesn't happen anymore. Your generation and now the younger people, even less. This stuff doesn't happen anymore and this has used to be commonplace. This has happened all the time.
“It's funny we sometimes don't reflect on how fast society and technology can change the day-to-day of interactions.”
Greg Raiz: It's funny we sometimes don't reflect on how fast society and technology can change the day-to-day of interactions. My daughters who were watching the Olympics with me and it's like, "Wow, look at all these commercials." and I realize we don't watch live TV anymore. That's the only live TV--
Sal Daher: "There are so many commercials. What is this?"
Greg Raiz: "What is this commercial thing? This is weird," because it's literally the only-- We don't watch a lot of live TV otherwise. It's things like that, that change the expectation of reality. This last year, so many people were on Zoom for home for work. This is completely upending our relationship with work, with telecommuting. As I think about the startups of the future, the startups that are going to be successful in the next decade, these are the ones that I get excited about that are transforming and changing our livelihoods and the ways we interact.
If you look at the last decade and the companies whether it was the Ubers and the Lyfts or the Instacarts or the Zooms, they end up touching so many pieces of the fabric of our day-to-day lives. I put that as a filter on what are the companies that are in the future going to have the potential to have similarly profound impacts on the ways we live and work.
Techstars Boston Is Leaning into the Coming Decade of Biotech
Sal Daher: Well, I'm glad that at Techstars, you have this focus on saving lives because part of that is investing in the life sciences, which is my focus now. I've invested at this point almost 70 companies, 66, 67 companies. I found that all the value in my portfolio seems to be in the life science companies. Also, the loss rate is much lower among life science companies. I've refocused, and I'm targeting life science companies. What you've been describing like the Ubers and all this stuff that's changed our lives, has been part of software eating the world as Marc Andreessen talked about that.
Greg Raiz: Of course, yes.
Sal Daher: Talked about back in 2011. I think the next decade, starting now 2021, is the decade of the life sciences, the decade of biotech. Because you think about all the infrastructure that made the software businesses so much easier to launch. The cost of launching a startup in the software world, just came down radically during that time, so many factors. Similar things are happening. They're not exactly commensurate because life science is very different, but there are a lot of trends towards, the technologies are cheaper, a shared lab space, 3D manufacturing. If we're creating devices, you're familiar with that.
All these things are getting to the point where we're going to have an explosion of these life science companies. With academic founders, they're not going to be richly funded, but they're going to have tremendous impact on humanity. And my... for me is how do I support these companies? Because they're going to be a lot of them, and the VCs are not interested. VCs are trying to do moon shot projects. They're trying to do mRNA, like Moderna, that's a VC project.
“I think biotech and medical specifically, Boston has one of the hottest markets, if not the hottest markets for many of those technologies.”
Greg Raiz: I think there's a couple really exciting things. One, I've been thinking a lot about Boston/founder fit. We talk about product-market fit, but it's actually important for founders to think about their markets of where they want to be, and where their customers are. A question I get a lot as the managing director of Techstars Boston is like, "Why Boston?" Again, we see a lot of folks saying why Boston in comparison to a program similar to Y Combinator, where it's out in the Bay Area. Again, it used to be that you needed to go out to the Bay, if you wanted to raise capital.
We've been fortunate and founders are super fortunate that there is a lot of flexibility for fundraising, because of Zoom that you can raise capital really anywhere in the world. From that perspective, the founder should really be asking what is the right market, where either my customers are, or there are network effects that could be really positive for my long-term growth? I think biotech and medical specifically, Boston has one of the hottest markets, if not the hottest markets for many of those technologies.
“...we have an incredible Fintech sector. We have an incredible robotic sector. We have incredible 3D printing sector...”
Again, there are lots of other technology fits for Boston, in particular, like we have an incredible Fintech sector. We have an incredible robotic sector. We have incredible 3D printing sector and other things like that, but founders really need to position themselves for whatever's going to help their ultimate company be most successful. It used to be, I just need to be in a location to raise the most capital. I think there's new dynamics that actually put Boston on either level playing field or in some markets in some sectors in accelerated playing field.
Sal Daher Talks About One of the Big Differences between Biotech Investing and Software Investing
Sal Daher: There are barriers we're talking about one barrier of geography, which is a barrier that is shrinking in many ways, but it's still important, but there are other barriers. A life science company just develops differently. I have experienced one life science company involved with, and they have a device. They had to build this device. The original device was handmade in the lab. Two years later, they have a supplier who manufactures a device for them. They don't have to have a PhD student tooling that thing. They can just spend a few bucks and somebody produces it at scale. The consumables, they have 'em cartridges. Now. They don't have to have somebody pipetting stuff anymore.
Biotech company, you can't talk about traction. What's a traction? What are your KPIs? "Well, we don't have to pipette anymore." It's a huge thing because then you can iterate much faster. You can have a lot more experimental cycles.
Greg Raiz: I think it's a great point. Every startup category has different metrics that give you an early indication of the track record or progress. A lot of times people say like, "Well, I don't have revenue," and I'm like, "I don't care if you have revenue." There's multiple ways to track KPIs, and there's multiple ways to track traction. Many consumer social companies have no revenue in the way they track traction, maybe daily active users. That's not a revenue traction. That's a, "Hey, can I get to break out success and scale for a product like a Clubhouse or a Facebook or whatever."
Other biotech and medical devices again, the traction is going to be early clinical trials or progress through the FDA phase gates.
Sal Daher: Most of these biotechs, it's way before they get clinical trials. There are pre-clinical trials or even before that to the point where the device is being used in research. That's what's really hard. Software investors are like, "Nothing is happening in this company." I think there's a lot that's happened but they're like, "Oh, it's the same. What are they doing?" "Oh, they're still doing this or doing that." "Well, that's what they do, but they're doing it much better."
They're outsourcing a lot of the drudgery to focus on their real business which is whatever process they're carrying out in the lab. Life science inventors don't know how ready the technology is because what works in a lab is very far from what works in the industry. There are whole bunch of reasons why.
Greg Raiz: Yes, absolutely.
Sal Daher Expresses a Need to Train Angels in Biotech Investing
Sal Daher: I think some kind of retraining, angel investor formation for life sciences is necessary. I'm noodling over how to do this and how to support angel investors in investing in the life sciences.
Greg Raiz: I 100% agree. I think there's a lot of opportunity, in general, to do angel training because a lot of angels-- I was in the same situation where I hadn't done a lot of angel stuff and I got involved in I think five or six different angel groups during the pandemic just so I would have maximized my deal flow because at the end of the day it's about muscle memory. You're getting better in biotech investing because you've made enough investments that you know what goes and what doesn't go.
It's that muscle memory that you're like, "Oh, I've seen this show before, I know how the story goes, and I know how this compares to something that's brand new." The same thing is true for me as well. Through my work at Raizlabs, I've seen and developed, and worked with enough founders that I know what product traction looks like. I know something that looks significantly differentiated from something that looks ho-hum. Again, that comes from muscle memory of having done either built hundreds of products or made hundreds of investments. We're seeing thousands of pitches.
“I want to accelerate companies that are really important and meaningful and I expect to get a capital return to allow me to do more of that.”
I think absolutely, there are ultimately for angel investors and I think this is a worthwhile exercise to think about why you're angel investing beyond the capital return. Again, I don't view angel investing as charity. I want to accelerate companies that are really important and meaningful and I expect to get a capital return to allow me to do more of that. For angel investors to think through, like, what are the types of companies that really matter to you, what are the things that are important for you to invest in because angel investing as you know, there's a high failure rate. If you're going to have a high failure rate, ultimately, you're choosing what domain of types of companies you're okay having a high failure rate.
For me personally, I'm okay having a high failure rate with companies that save lives because at the end of the day, even if 90% of my companies fail, the 10% that have some success, I'm like, those effectively save people's lives, I think that's pretty important and valuable. There are other sectors that are equally exciting and interesting. Again, I'm not downplaying any of the other fields. I've invested in B2B, I've invested in SaaS, I've invested in Cloud and other things like that and it's just understanding why is this particular field area entrepreneur important for me to invest in?
Sal Daher: Great. Let's pick up a little bit on what you guys are focusing on, Techstars. Offline, we mentioned medical device companies, what's going on there in the medical device space?
Greg Raiz: Like I said, I'm particularly interested in saving lives, saving the planet, or changing the way we live and work. I think specifically in the saving lives category, there's so many innovations that can and are being developed. Because of Boston, a strength in the hospital, again, we have one of the best hospital networks and some of the most profound facilities doing incredible clinical research and incredible surgeries and things like that, it does end up being a ripe target market for medical device companies to really ascertain whether there's a there there, whether they have a need, whether they're building something truly revolutionary.
I was talking to a founder earlier this week. She was out of Australia building a really innovative medical device product. She recognizes the strength of Boston and her questions is around, "Well, who can help me with supply chain and what the right contacts with the FDA?" She views the American market as the right place for her to grow and show that traction. It's really, for me, within Techstars, it's thinking through what are the phase gates that I can help accelerate her business to be successful?
Again, some businesses will be successful, some businesses won't, but if I can unlock the access of the network and the doors for some of those conversations, ultimately, that company should be more successful than if I hadn't done that.
Sal Daher: Is there a particular company that you would like to talk about? Companies are always way more interesting than general concepts.
Greg Raiz: Right now, you're catching me at an interesting time where Techstars Boston literally has their applications closing today. I have 300 and some odd companies that have applied. We haven't made our selection and we won't be making those public until further on down the road. I can't really speak about a particular company on that front, but collectively, just some amazing companies and entrepreneurs. I think for startups, looking at acceleration programs, it's really thinking of them as an investor, as a partner, as effectively a co-founder, like, what is the right program and what is the right city for me to be in, as opposed to, "Hey, here's a check."
Techstars generally invest about $120,000, up to $120,000 in each startup that we accelerate. Ultimately, for that startup, they should really be looking for-- you've heard this expression, smart money.
Sal Daher: [laughs] Yes. Well, Techstars is about as smart as money gets.
Greg Raiz: That's our hope. [chuckles]
Check Out Greg Raiz’s YouTube Channel – Half Ideas
Sal Daher: That is awesome. Now, I understand that you have some videos that you've been putting on YouTube, tell me about those.
Greg Raiz: When I first started my business, I started blogging, because blogging was the thing that you did in early 2000. My blog got traffic and it helped me think through some of the topics and some of the things that ultimately became Raizlabs. When I started thinking about going on my own, I was like, "I want to put content out into the world and I need to find whatever the new modern medium is."
It wasn't blogging. Blogging is great and I still do a little bit of that, but it's very hard to reach audience unless you want to curate a newsletter. I had done podcasts, and I enjoy podcasts but I'd rather be a guest on a podcast than host my own. I'd always been fascinated by video content. For me, it was a learning exercise. I created a YouTube channeltube.com/halfideas around entrepreneurship and just started producing videos and learning the process of making them. It's been just fantastic to both dive into a number of different technology fields, both technology and design, which is the intersection that I'm interested in.
Then specifically diving into topics of angel investing, venture capital, raising funds, advice to founders. For me, it gives me an opportunity to get my message out to many founders that again, I can't have every single conversation with founders. On YouTube, I get actually thousands of views now a day of different people viewing my content of, "Hey, what's the difference between angel investing and venture capital? Or how should I think about enterprise sales? Or what are the right ways for me to think about an accelerator," or what have you? It's just been a creative outlet for me. It's been a lot of fun learning stuff, learning the medium, and man, making content's really hard. [chuckles]
Sal Daher: It's very hard. [laughs] It's very hard. Getting it found is really hard. Let me give you the URL for this as well.
Greg Raiz: Hold on. If you just do youtube.com/halfideas, it should work.
Sal Daher: Half ideas on YouTube.
Greg Raiz: Yes.
Sal Daher: Go on YouTube and search for half ideas.
What Are Half Ideas?
Greg Raiz: Yes, you should find it or just search my name, you should find it. The idea for half ideas was when I was CEO of Raizlabs, I used to always tell my employees that I have this half an idea. I would say that because it was disarming, I didn't want them to think, "Oh, I'm the CEO, I'm telling them what to do." I wanted to say, my style of leadership is I want people to come along on the journey with me. I want them to feel the ability to poke holes at my ideas and find something that collectively we think is the right thing to go do.
I may say something like, "Oh, I have this half idea that maybe we could do X and that would be better." That way, they don't feel like it's the CEO telling them they have to do something. I'm really looking for the reaction and their input to fill in the other half, like, do you think this is good? Or is it should we go in a completely different direction? That phrasing has always led me to discover all sorts of new things that I never would have dreamed of doing myself. That was the idea of the channel as well as like, "Let me put some half ideas out to the world of cool, interesting things." I'm thinking about, and let the community discover them and engage with me as well, so it's been a lot of fun.
Sal Daher: That's tremendous. I'm a little daunted by creating video because the ante for production value goes way up. With sound, you just have to make sure you have very good sound. What you can do with sound, you can edit it a lot, so that a lot of the ums and ahs are taken, out and you sound really coherent and so forth. Video it's harder to edit, and then you have to have much higher production values. You have to have such that visually interesting. Talking head doesn't sell.
Greg Raiz: I don't know, like I've had videos that have been very successful, and gotten lots of views, that were really about the conversation and the topic. I think it depends on the topic. Ultimately, if you can keep people's attention, and keeping people's attention on a podcast for an hour is hard. Again, if they're trapped in their car maybe that's easier.
Sal Daher: Yes, that's the use case, is a commute. People say 45 minutes I listen to a conversation, and I hear about a couple of startups. I hear a founding story, and I hear how somebody built the career. That's the use case.
Now, with YouTube, for somebody who's going to be focusing aurally and visually at the same time. That means that the person is searching, is doing research in the field. They're looking for knowledge in that particular space.
YouTube Is the Number 2 Search Engine
Greg Raiz: Yes, and that was the aha, at least for me was that YouTube is the world's number two search engine. People start their search on either Google, or in the second one being YouTube. Again, it's not great for everything, but for me, I was trying to create those relationships with audience. It's been just really fascinating to learn that platform, how it works. Again, at the end of the day, content is content. You create compelling content you can-- like I'm sure Sal if you wanted to create a YouTube channel and focus on it, you'd be great at it. Just because you have the eye and the ear for it. It does take time in either direction.
Sal Daher: You do learn.
Greg Raiz: You do learn.
It’s Hard to View or Listen to One’s Early Content
Sal Daher: I can tell you that. Your technique improves over time, and you figure out what engages people, what doesn't engage people.
Greg Raiz: I can't watch my old videos. It makes me cringe.
Sal Daher: [laughs]
Greg Raiz: But it's probably the same thing for you and some of your early podcasts. You've learned and you get better.
Sal Daher: Like some of my earliest podcasts I had Michael Mark was my first interview. I was terrible. I couldn't stop talking in the podcast, and I should have just shut up and let Michael talk. [laughs] That's the first thing. It's just less. Less Sal was the big lesson that I took on. My daughter was very good at this. It's like, "Let the person talk. Let the guests talk."
Greg Raiz: That's awesome.
Sal Daher: Because I have an adult daughter, who is an avid listener to the podcast, Coach of the Host.
Greg Raiz: Nice.
How Greg Raiz Discovered Computer Programming
Sal Daher: Let's talk about discovering your career. Let's go back when you were a high school kid in Newton. How did you figure out that you wanted to go into software?
Greg Raiz: I remember I went to high school in Newton, and then to BB&N in Cambridge. I remember it was one of the early computer science classes. I think it was either Logo, or some kind of early Basic class. All of the other students, again, the teacher would be like, "Hey, we're going to do something simple like a four-loop, or count to 10," or something of that nature. Everyone was having trouble with it, and I was like done and playing with other stuff. For me, it was just magnetic. My father was actually into software, so to some extent, it runs in the blood. He started Revit which was-
Sal Daher: Oh.
Greg Raiz: -a well-known 3D CAD company, so I had big shoes to fill in terms of entrepreneurship. I'd always just internally personally been interested in computer science, and the idea that I could type keys on a keyboard and make cool things happen. I remember as a kid, my friend had a Commodore 64, and he wasn't able to afford a hard drive or disk drive for the computer. The way we would play is like he had a programming book, and we would literally type in a game from a coding book. We would type the game, we would play for--
Sal Daher: [chuckles] You wrote the code, you had to load the code every time, every instance?
The Vast Horizons of Software
Greg Raiz: Yes, I went to typing in the code every time we play the game for a couple hours, and then our mom would be like, "Time for lunch," and we'd shut off the computer and it was gone. That was my very earliest programming experience but I felt it was such an empowering tool that you could literally make anything you want. I think to this day, the imagination, literally anything you can think of its hands-on keyboard touching and you can make all sorts of different-- You can build any large company in the world today in the Facebooks, Googles, Apples, Amazons, whatever, it's all typing on keyboards and doing something really extraordinary.
There is this power and awe that comes from that. That has always fascinated me. My first job out of college I studied computer science in college, but I got a job at Microsoft working on the Windows XP operating system. That's where I got more of the passion for design and it was this notion of like, "Wow, you can have this amazing company that can do all these things, but it's really about making things easy and intuitive. I would remember going to the usability lab and watching people struggle to use computers, which were so natural and easy for me.
I would watch them just clicking all over the place, trying to do something simple, like changing the wallpaper on their computer or trying to send an email, and just being completely flustered and lost. For me the empathy of this shouldn't be hard. I could see people struggling with it and I understood why it was hard and I was like, "Man, we, we really need to think about accessibility and ease of use," and all of those things.
How Bad User Interfaces Create Inequality
Sal Daher: I see it hands-on because I own apartment buildings and I use Buildium and Buildium has apps and all that stuff designed for the average American who was quite conversing with apps younger people. My tenants are typically immigrant populations who are not unless you're like 18 years old, but if you're somebody in your 30s, you're not really very conversant with apps and just like, just opening up, just finding your email address on your phone. They know how to use WhatsApp, but they don't know how to use the email because they've never used email, but the thing runs on email, you need to sign the lease on the email and all that stuff. Oh, it's like, I'm a customer assistance desk.
Greg Raiz: People who are familiar with technology and computers, they intuit a lot of things that they think are easy. We will look at a screen with a label in a white box and we'll be like, "Oh, that's an input field, we need to type something in there." People who are not familiar with computers.
Sal Daher: Do I type outside, where do I type?
Greg Raiz: A, it's a white box. They're like, I don't know what to do. Again, we assume it's intuitive that I need to click in the box and the keyboard comes up and that is not normal. We are the minority, the thing that's super eye-opening and I do recommend this to most founders is to run usability tests and it's not a complex, scary thing. It's a go into a coffee shop or send your app to someone who is non-technical. My family, I've subjected them to a lot of usability tests where I'm like, "Hey, try this." You learn things that are intuitive to you but are not generally intuitive and it's through repetition that you make your product easier and simpler to use, you remove the steps of friction.
We're so accustomed to apps and software and websites and login screens and confirmations. It's going to text me a link and do that all those little pieces are friction and all of those friction lead to lower conversion rates, lower satisfaction, lower retention, and the companies that are really, really successful, you have to look at the details. They are really detail-oriented around every step of the process and every screen is very intentional and every word is very carefully chosen. Being a student of that, especially in the apps that you're like, why do I keep coming up on this app? What are the apps on your home screen? How did you even discover them? What is their onboarding flow that makes them so compelling?
The same is true again for non-consumer apps as well, for business apps. Why is Slack or Dropbox or Salesforce, why do these products work better or are more successful than many of the other products that don't get the later day?
Sal Daher: Slack is an excellent example of that and previous generation Apple in its obsession with experience tremendous.
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As we reach the end of the podcast, I like to open up the forum to my guests and just say, what would you like to leave my audience with this audience of people who are founders, angels, people who'd like to start companies, people who are working in startups, what would you like to communicate to them, that we haven't covered?
PURE GOLD: Greg Raiz’s Parting Advice to Angels & Founders
Greg Raiz: Yes. I think for founders, for angels to collectively lean into the relationships and helping one another. Help is not necessarily writing a check, looking at this right now, we have an incredible mentor network and a lot of mentors who are like, "Hey, I want to help, but I don't know how, like if you're working with a founder or if a founder has pitched you, the easy thing to do is say, "No thanks, that's not a fit." The hard thing to do is write them a page of feedback on what you liked about the deck and what you didn't like about the deck.
Founders often get this like, they don't get a lot of feedback. They send in a lot of pitches and they hear a lot of nos, but they don't hear a lot of, "Here's what I liked or didn't like." If you're an investor angel, try people's products, like it's surprising how many people don't kick the tires in the website or don't create a free account or don't like, if it's a consumer product, go spend 50 bucks and buy the product and tell the founder, why you think it's awesome or why you think it's junk.
At the end of the day, if founders and angels can create more of a feedback loop, it will accelerate the learning. Ultimately, it's the learning that leads to traction that leads to funding that leads to success and builds those relationships. For an angel, if you send the founder a feedback and a month later, the founders like, "I listened to everything you said, I agree with five of those and I actually took action and it helped me. Thank you." Do you think that the angel is going to be more interested in the company or less?
Sal Daher: The angel’s going to be very impressed because that founder is displaying the quality of coachability.
Greg Raiz: Exactly.
Sal Daher: Which is one of the most important qualities for a founder.
Greg Raiz: That value that the founder gets is equal to the value that the investor gets because a lot of times investors who do give feedback, they never hear back again.
Sal Daher: Yes, after falling off the chair, the investor will think very highly of the founder.
Greg Raiz: Yes, and it's leaning into the relationship. Again, if angels can engage with founders and founders can equally engage with investors, again, not every relationship is going to end up in, "Hey, I'm participating in your round," and that's fine but collectively, if you're building stronger relationships, you're building more trust and my belief is that stronger trust leads to more rounds, more traction, more success.
Sal Daher: Yes, that is very true. That deserves to be said very frequently to founders and to angels to understand that the angels to give the feedback, and to founders to listen and cause an angel to fall off her chair in surprise that her advice listen to.
Greg Raiz: I've given some bad advice too. So take it always with a grain of salt but when you do that repeatedly, you'll start to see those trends in those things that are like, "Okay, I've heard this feedback. I should act on it."
Sal Daher: I think the best advice is the advice that’s sort of like, it's the third time you've heard it and it's like, "Everybody's telling me, maybe, I need to change my pitch. Everybody's telling me that I'm burying my lead. I'm burying my theme in the pitch. Maybe there's something to that." That's really valuable.
Greg Raiz: Awesome. Sal, thank you so much for having me really appreciate being on the show.
Sal Daher: Well, Greg, this is great fun, I've been hoping to get you on. Really grateful that you made the time and I hope that it's profitable for the listeners.
Greg Raiz: Yes. No, it's been a great conversation and yes, love to give back to like I said, the Boston ecosystem and the greater angel and entrepreneurship community, so just thanks so much and hope to hear from many of you.
Follow Greg Raiz on YouTube and on Twitter @graiz
Sal Daher: For listeners, remember YouTube Half Ideas. Remember the focus that Techstars Boston has that Greg is running. If you want to run through that again.
Greg Raiz: Yes, sure. Folks want to check me out they can follow me on Twitter @graiz or on YouTube as Half Ideas. Just excited to meet many amazing companies as part of Techstars Boston. We're going to be hopefully hosting more in-person events as the world hopefully returns more to normal.
Sal Daher: God willing.
Greg Raiz: God willing. I think there's a lot of opportunities. I'm just excited to accelerate entrepreneurship especially for the companies that are profoundly changing humanity.
Sal Daher: Awesome. Thanks a lot. This is Angel Invest Boston, I'm Sal Daher. Thanks for listening.
Greg Raiz: Thanks, Sal. All right.
Sal Daher: I'm glad you were able to join us. Our engineer is Raul Rosa. Our theme was composed by John McKusick. Our graphic design is by Katharine Woodman-Maynard. Our host is coached by Grace Daher.