Stephen Cummins talks with Tyler Koblasa, Founder and Ex-CEO of CloudApp – a platform enabling instant collaborative communications via shareable videos, GIFs and screenshots. Tyler is now CRO of Invisible Technologies.He talks about his career, the value of building an agency targeting the domain where you intend to build software, Los Angeles v San Francisco for startups, why StartUp Weekend v Hackaton for creating a new business idea, mentorship, the value of bootstrapping …… “Moving over to San Francisco you jump into this massive pool and, you know, it’s easy to drown on it. It’s also easy to get distracted and just, you know, from different companies with their inflated valuations and, you know, raising these large financing rounds to then seeing, you know, them all – many of them also die because the revenue wasn’t there.”
TRANSCRIPT
Episode 15
0:00 Tyler koblasa (excerpt) “And, moving over to San Francisco you jump into this massive pool and, you know, it’s easy to drown on it. It’s also easy to get distracted and just, you know, from different companies with their inflated valuations and, you know, raising these large financing rounds to then seeing, you know, them all – many of them also die because the revenue wasn’t there.”
Stephen Cummins
0:47 In this episode we have Tyler Koblasa, CEO and Founder of CloudApp, a platform that lets you record, host and share a visual media to enhance your conversation.
Stephen cummins
0:57 Tell me a little bit about how about you where you grew up and… and little bit about you as a person.
Tyler koblasa
Yeah. So I… I grew up in Los Angeles, Dad worked in entertainment and, so he spent most of his career in that and I kind of shied away from it. Started writing code in high school. This is kind of the beginning of the journey. That was kinda the early 1.0 period. And we had an early hosting company that I launched during high school. Been an entrepreneur now for about 20 years and just have always loved building stuff. That kind of led into working with other early stage companies during dotcom 1.0, and moving up to San Francisco for the first time around 2,000 – then saw it all collapse and, moved back to Los Angeles – was enjoying the weather down there. But, yeah, I grew up and grew up in LA and I’ve love always building stuff.
Stephen Cummins
You founded it a couple of interesting companies in Los Angeles, earlier in your career. What were those experiences like?
Tyler koblasa
2:14 You know, kind of coming back to the whole aspect of building … You know, I’ve always thought about if there’s a problem to solve it. And, definitely it’s been a journey. I think the reward has always been if you build something and people actually use it – and even more so actually pay for it, you know, you’re creating value and it’s a value exchange. That journey, I would say, as a teenager and early twenties – as a entrepreneur back in the day was much more difficult to find other entrepreneurs to work with especially technologists so definitely felt pretty alone. You might need a few other roles here or there – but I think on of the lessons I learned (and also through the later companies) around the power of advisers and mentors … and I think as an entrepreneur it’s incredibly important to find any type of mentor adviser that’s been there before to work with. But, yeah, those are definitely learning experiences. And I think the other thing is getting into focus and, you know, we at the time kinda shred ourselves thin – got into multiple different lines of business which ultimately lead to more distractions and taking your eye off the ball and so forth.
Stephen Cummins
So focus and double down on one thing and then get some amazing mentorship … they’d be two things you would advise other entrepreneurs to really look at when they’re early on in their careers.
Tyler koblasa
Definitely… definitely and also just really understanding that… that funnel. So getting as quantitative and qualitative as possible. I wish I did that some more early on, you know, talking to as many of your customers as possible and trying to validate assumptions. And it’s hypotheses. And also just really trying to get that sales and marketing machine going earlier.
3:49 I think commonly founders are builders, makers, dreamers …. and if the ways to externalise that and get the word out and then validate your messaging earlier – that’s one thing that I definitely would have done differently.
Stephen Cummins
Does that give you a sense of satisfaction happiness? … Now that you would have your own methodologies and for you it’s a process you’re comfortable with – building and scaling a company.
4:13. Do you really do appreciate that all the more having gone through all of that.
Tyler koblasa
Yeah. I would definitely say going through those struggles of entrepreneurship and the challenges that lead you to see patterns that you’ll recognize – and then obviously plays into future businesses and other entrepreneurs you work with.
Stephen Cummins
So, when you moved to San Francisco and then created Mingly for managing and nurturing relationships online, how different was this? … you know, building a company in San Francisco compared to LA.
Tyler koblasa
Well the tech ecosystem in LA was a small pond – pre silicon beach, as they call it .. and moving over to San Francisco you jump into this massive pool and, you know, it’s easy to drown on it, easy to get distracted with these different companies and their inflated valuations … and these large financing rounds … to then seeing many of them also die because the revenue wasn’t there. So I think definitely it’s easily been a place you can get distracted. There’s a lot going on, but there’s also a rich pool of intellectual capital. So if you can focus and be selective, I think anyone that gets through the first year – there’s just so much going on you want to go to everything – will progress… but definitely there was a lot to take in.
Stephen Cummins
One thing I noticed about you was, and it… it plays into what you’ve just said … you don’t seem to be the type of guy that goes running after venture capital early on. You seem to prefer to build users and build customers and get that product market fit rather than give away a chunk of your company at the beginning … at least that’s the impression I get looking at how you’ve you raised a little bit later on with your current company. And I think you raised about 500K with Mingly and exited with that. Is that part of your philosophy? Do you believe in doing that?
Tyler koblasa
Yeah, I think it’s common misconception that financing is an answer to the problem. And I mean that’s just fuel in the gas tank … if you can operate as financially lean as long as possible early on, you’re going to be able to iterate on a product to find product market fit and ultimately product channel fit for distribution. And I think definitely entrepreneurs commonly will look at financing rounds as milestones to put money back into the gas tank or fuel. But as long as you can operate in an efficient manner and commonly leveraging, whether that be remote teams and, whether that be far away places, I definitely highly recommend it …. but also just trying to bring that communication together which also creates challenges.
Stephen Cummins
You helped lead product and customer development in Hero labs for amazing clients like IDEO and StartUp Weekend … and it must have been a kaleidoscope of incredible learning experiences. So how was that in terms of your personal development as an entrepreneur.
Tyler koblasa
I think consultancies provide you with the ability to have insights into many different businesses and also leverage patterns you’ve seen before as an entrepreneur … so they commonly use the phrase ‘intapreneur’. So if you can take lean start-up philosophy, lean UX and bring that into a problem set to validate that early on before a company goes and spends, you know, large sums of capital trying to build and solve something incorrectly … I think that experience really let us work with early stage companies and clients like IDEO. And the Startup Weekend project was fascinating.… we built a platform called Startup Digest which is a global network of events taking place around the world. I think it’s the largest collection in the world. And we did that with Up.co which is the parent entity before it was acquired by text.
Stephen Cummins
Kaleo as well was one of your customers. I think wasn’t it. (yes!) … You had a relationship before that I think with Startup Weekend and that’s ongoing for you .. tell me a bit about that.
Tyler koblasa
Yeah. So the early Startup Weekend experience was back in around 2008.
8:56
And we’d always heard about Startup Weekend. A close friend of mine named Josh and I … and we were always considering flying out to Colorado to do a Startup Weekend, then we found out, hey, they’re going to be hosting one in Los Angeles. So we bought our tickets, showed up and pitched this concept, which at the time we called Mingly – which is about being able to nurture relationships throughout your network and making sure that they don’t slip through the cracks. Yeah. And we pitched that … ended up winning the events and then .. you know, that kind of catalysed over a series of 48 hours starting that company. Then we started to work with a group down called Idea Lab and Bill Gross in Los Angeles – one of the early incubators of all the first dotcom 1.0 companies. The Startup Weekend after that event … we were asked to start organising that …. we brought it to Santa Monica to a little co working space called Coloft and met another couple of close friends and I think we did a series of like 8 to 10 events there over the years and we had many companies come out of there. One of them called Zarly. We had Ashton Kucher on the judging panel. Ashton had been investing in Zarly .. and they brought Meg Whitman on their board. There’s another company called Lootcrate that also launched out of that Startup Weekend events and they went on to be a huge success. So I think the whole aspect of Startup Weekend, if someone is considering entrepreneurship or they’re a seasoned entrepreneur … being able to find other that are kind of in that same time in their life … I think that journey being able to connect with others and be able to tap into that global network has been phenomenal. I definitely made some very close friends through that community.
Stephen Cummins
Isn’t it insane what people can do when they really focus and they just go crazy for 16 hours for a couple of days in a row … isn’t it insane what thy can do?
Tyler koblasa
It’s definitely mind blowing because I think we today, you know, we… we definitely struggle with like how long things take and with scope … and longer blown out product requirement documents.
11:04
Startup Weekend is a little bit different to a hackathon where you have business people and marketing people also thinking about the problem not just devs. Yeah. But just to be able to have a hard deadline – you can actually time box something that is actually validated and potentially has maybe, you know, a potential customer lined up. But to the point of like focus, I think it’s definitely powerful.
Stephen Cummins
And when you pitched Mingly, did you do that with a friend? Or did you guys actually find anyone else there that ended up working with you?
Tyler koblasa
I pitched the concept. We had a team with a gentleman that was at Hulu … we also had someone else on the team that was coming from the NBA business side. A brilliant HPS person. And also my friend Josh … we worked together that weekend and. There was this vision around how do you nurture business relationships. And ultimately, you know, the business we ended up winding it down because it was really more of like a B to C business. And then that kind of led into future endeavours of really focusing on B2B and SaaS. But I think the problem still exists – there’s a great company today chasing the same problem called Cloze. And there’s been quite a few companies that have gone after this problem. But yeah it’s a challenge.
Stephen Cummins
Yeah, it’s red water. It’s a very competitive space. Congratulations! Yesterday. You pitched. I believe the theme was the future of work – obviously connected with CloudApp – for the judges here at Pitch and it’s very difficult to make the semi final. It’s whittled down from. 70 great companies get invited over here. So to make the semi -final was unbelievable. Tell us a little bit about what your pitch about yesterday.
Tyler koblasa
Yeah, I think the… the pitch was really around how can we kind of bring that message and the value prop together and concise manner to communicate that to .. they had like judges piled on there …which was nteresting. And I think just the opportunity to bring what we do to the surface of the audience was awesome. I’m just kinda connecting with other companies in the group and hearing their journeys their stories – different stages of companies, all different dimensions and verticals. We’re definitely honoured to be a Collision and, you know, part of this.
Stephen Cummins
And that’s one of the beautiful things about entrepreneurship. I think people are out there competing, but when entrepreneurs get together, they understand what each other are going through – even if they’re in different stages in different businesses. And there’s always a great sense of community at events like this …..
14:20
Next episode is the concluding one with Tyler Koblasa. He goes a little deeper into CloudApp, and chats about innovation, work-like balance, self awareness as an entrepreneur, his daily routine, some thoughts around technologies like machine learning and augmented reality.