Episode 6: Lessons on Resilience & Growth from a Tech Startup Ecosystem Expert with Ian Massingham

Mar 7, 2023 | podcast | 0 comments

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You can find the full transcript for this episode at the bottom of this page

No matter how far you get in your career, how visible your role is, or how many career wins you have under your belt, none of us are immune from experiencing fear, self-doubt, or anxiety.

However, because so many leaders don’t share this more vulnerable part of their story, there remains a pervasive myth that successful leaders are exempt from experiencing these feelings, particularly in the startup ecosystem. This is why I’m so grateful that this week’s guest on the show is helping to bust this myth by sharing some of the mental and emotional challenges he’s faced throughout his career and what’s helped him overcome them.

In this episode Ian Massingham, a leader in the tech startup ecosystem, shares his fascinating story about getting into cloud computing back in its infancy, and how he went on to help hundreds of thousands of startups around the world. First, through his highly visible role at Amazon Web Services (AWS) and more recently through his position as VP of Developer Relations and Community at Aiven

In this episode you’ll get a glimpse at some of his career successes, but not without a look at some of the challenges that he’s faced throughout his career supporting the startup ecosystem, including how he’s overcome them. Tune in for his tips for creating boundaries between work and personal life, overcoming fears and self-doubt, and making the most of receiving critical feedback. This is an episode you don’t want to miss!

“You can experience very intense working periods where it feels like you have no life outside of the office, you sort of commit everything to that. And I think one piece of guidance, I would say is, you can do that, okay, but you should always be sure that if you’re doing that you’re conscious of what you’re doing. You know, you’re spending your whole life tipping everything you’ve got into your work into a company or into your job, then what are you degrading as a result of that?”

Ian is VP, Developer Relations & Community at Aiven, a series-D open source data infrastructure startup headquartered in Helsinki Finland. Prior to Aiven, Ian held a similar role at MongoDB, and before that he spent almost 8 years at Amazon Web Services. His final role at AWS was Global Director, Worldwide Solutions Architecture for Startups. Before the pandemic, Ian was a very frequent traveler and public speaker in his roles at AWS, traveling and speaking on behalf of AWS at customer and developer events across the globe.

Beyond work, Ian lives in North Yorkshire in the UK (close to the real world location used to film the Hogwarts Express and Hogsmeade Station in the Harry Potter movies) with his long term partner and their children.

The ‘personal info’ listed on Ian’s Twitter bio is ‘🖤. Skier. Kettlebell aficionado. Spaceships. (he/him)’ Tune in to the full episode to learn the meaning behind the 🖤.

What You’ll Learn in this Episode:

  • What’s helped Ian to succeed in a highly visible, public facing role despite the inevitable critical feedback
  • The mindset that Ian observes in the most inspirational and effective startup founders 
  • How Ian defines the difference between imposter syndrome and self-doubt
  • The challenges Ian faced at the start of the pandemic that impacted his personal and professional life, and what helped him get through this difficult period
  • Ian’s advice regarding creating boundaries between personal and professional life when you’re working in a startup or a high growth organization
  • A mindset strategy that helps him overcome stress, anxiety, or negativity

Find Ian Online:

Resources & Inspiration from the Show

  • List of resources to help you find a coach, therapist, or peer support If you’d like additional support for your mental and emotional well-being as a founder

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About Founders’ Fears & Failures and your host, Dr. Melissa Parks

Melissa is an entrepreneur, former therapist (PhD in Clinical & Health Psychology), and an executive coach for entrepreneurs with a special focus on startup founders. Her passion for supporting startup founders in particular began after witnessing firsthand the emotional rollercoaster her husband experienced as a startup co-founder.

She started the Founders’ Fears & Failures podcast with the mission of shining a light on the mental and emotional challenges that come with life as a startup founder. Having lived abroad for 10 years herself she realizes how much we can learn from hearing stories from around the globe which is why the show doesn’t focus on a country-specific startup ecosystem.

Melissa is also the co-founder of the Location Independent Therapist Community, and a mom to a toddler who keeps her on her toes, and fuels her passion for helping to make the world a better place.

If you are interested in coming on the show, please get in touch. We would love to hear your story.

Want to connect further? Get in touch with Melissa on social media:

Want to work with Melissa?

Melissa is a former therapist who now provides mindset coaching for ambitious professionals around the globe. Schedule your free discovery call HERE.

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Did you enjoy listening to this episode? Leave your review on Apple podcasts or Spotify.

Disclaimer: The Founders’ Fears & Failures is for educational, informational, and entertainment purposes only. It is not meant to be used for personal health advice and should not be construed to constitute personal or professional consultation or guidance, or to replace medical or mental health treatment. The opinions expressed by this podcast, including the podcast guests, are not meant to replace the advice of your healthcare provider. Always seek the advice of a medical or mental health provider regarding any questions or concerns you have about your medical and/or mental health needs. If you are in crisis, please visit this website to find a list of suicide hotlines around the globe. 

Episode Transcript

Melissa 

Thank you Ian, thank you so much for joining me on the show today. It’s really great to have you.

Ian 

It’s great to be here. I appreciate the invite. Yeah.

Melissa 

So. So we met a few years ago, at the Web Summit in Portugal. And you shared with me, we met at a dinner and you shared some of the challenges that you had faced as a leader in working in the startup ecosystem. So I’m really looking forward to diving into some of those challenges today. And again, thank you for being on the show.

Ian 

No problem

Melissa 

Yeah. So before, before we dive into that part of things, why don’t you just tell us a little bit more about how did you get into the world, You worked at AWS, What got you into the world of cloud computing?

Ian 

Yeah, that’s a long story. You know, I’m definitely in the last a third of my career. Now I’m 49 years of age. So I’ve been in tech for a long time. I started in tech in the mid to late 90s. I remember, my first job was in the Internet services space, were back when accessing the internet and services online was still new and novel that was in ’96, that I started working actually October the sixth 1996, I still remember the day I quit college. At the end of my second year, and I would say that I was not somebody that got on well with university life. In fact, I was writing a bio recently for my school, they asked me to write a bio. And one of the things that I shared in that bio that I wrote was that the sort of the unstructured nature of living in a large city, having come from quite a small town living in a large city and having to manage my own, my own schedule, my own attainment at university just did just did not agree with me. I just for some reason did not get on with it. Well, I had a lot of struggles. And I left university at the end of my second year, really to take what I considered to be a really good opportunity in this internet services company. And it was really early then. At the time, there were only about 400,000 internet users in the whole of the UK, which is kind of unbelievable. Now everything we do is online, but back then it was really novel. And I was lucky to join an organization that was in a hyper growth phase. You know, during the period that I was there, in the first couple of years, internet access became mainstream and actually worked on a service that was pivotal to the rise of consumer internet access in the UK, where I’m obviously from, and obviously still located, service called Freeserve. This service was unusual in the removed the need for customers to pay a regular monthly subscription to access the internet, it was over dial up. So you know that weird noise when

Melissa 

I remember that!

Ian 

It was all about that. But during during the couple of years that I was there, internet access in the UK and the use of online services became completely mainstream. It was the rise of retail with Amazon obviously becoming very popular between 1997 and 2000. And actually lots of other services like banking and media consumption and news. They all moved online during the first five or 10 years of my career. And I was working in precisely that space. So it was hyper growth. And because it was hyper growth, incumbent organizations started getting into the Internet access business, most notably telecommunications operators. And the company that I was in with got acquired by Telco. I stayed there for quite a while I was part of a corporate turnaround in the organization, which is called energies and then later that was acquired by Cable Wireless. And that sort of period in my career, took me up to about 2010. In 2010, I moved into my first what I would consider pure tech or big tech company, which was an enterprise organization called EMC. It’s now part of Dell. They were selling data storage infrastructure and software. And I went there to work on cloud computing services. But again, turn the clock back a bit around 2010. All the big telecommunications operators like the BTS, the Deutsche Telekom, the France Telecom, the Telefonicas. They all thought they could build cloud computing services to compete with this upstart Amazon Web Services and Microsoft Azure and they honestly believed that there would be national cloud providers in each country, and that the telecommunications operators would be running them. That was how, if you talk to a telecoms exec in 2009, 2010, 2011, that’s what they would tell you. You know, maybe naively, I also believed that that would happen and I went off to work at EMC trying to help these telecommunications operators build cloud computing services. You know, like a lot of good ideas, that idea didn’t really survive its first contact with the reality. And the reality being, you know, AWS and Microsoft and later Google, they turned out to be really effective innovation machines when it came to cloud computing. You know, it was interesting, particularly for Amazon, they were a retailer, they became a very, very successful technology business. Microsoft were a software company, they became a very, very successful technology infrastructure business. Google, a digital advertising company also became a very, very successful technology, infrastructure business. And weirdly enough, the Telcos who were very successful infrastructure businesses did not become successful in cloud computing, which, you know, it’s kind of interesting, but a separate story in its own right.  So when I was at EMC 2010, of course, I started learning about what I consider to be the real clear cloud, you know, AWS and the other providers that have similar delivery models. And I was really enthralled. By a few things, I mean, the first thing I was enthralled was by was innovation pace, they seem to create services and throw them out with a degree of velocity and have an appetite for innovation. That was just unheard of. And really unusual for me, given my time working in telecommunications, very slow moving and conservative orgs, they don’t move fast when it comes to service innovation. I found AWS from the outside really interesting, simply the rate at which they were throwing out new services, generating new services and launching them at that point. And of course, that was nothing compared to what they do today in terms of pace of innovation, but it was still really fast relative to what I’d experienced elsewhere. And when I started digging a little bit more into why this was, the second thing that I became really enthralled by was their culture, their leadership principles, which they still use today, of course, to hire, promote, and drive the business over there at Amazon and AWS. And I really wanted to be part of this, I thought this is going to fundamentally change the way in which technology is done. It’s just completely unlike what we’ve seen before, it’s genuinely revolutionary, that people will no longer buy and operate their own infrastructure in their own software, but they will consume it as a set of services from the cloud. And I felt that this would have improved, right, I felt this would have really, really big economic impact, really big organizational impact, and would really be truly transformational in so many different ways. And one of the ways of course, it’s how it enables how it enables startups how it enables downstream innovation. So I really wanted to be part of this. I started applying for jobs at… recently, I found my my first rejection email from AWS, which it turns out, I sent in January, I think, 2013, I applied for a solutions architect job there. And I got to know, you know, we’re not looking to hire you for that particular role, which I was disappointed about. About eight months later, they came back to me and said, actually, how about developer relations? How about evangelism, as it was called then? And I was like, Yes, please. I interviewed I had no experience of developer relations, no experience of evangelism, but for whatever reason, they decided they’d offer me the job anyway. And

Melissa 

Fantastic! They made a good choice.

Ian 

I joined AWS in December 2013. And yeah, the rest is history. I worked there for about eight years in developer relations and evangelism, and then in leadership for that function. And then at the very end, for the last 18 months, I worked in leadership for their startup solutions architecture team. So this was working with, you know, hundreds of 1000s of startup organizations around the world through my organization. And helping brand new companies make their ideas a reality using AWS as cloud computing technology to do so. So that was the last 18 months of my tenure there. I actually left AWS in in September 22, and did a year of MongoDB. And then more recently, on October last year, October 22, I joined Ivan, which is a data infrastructure startup headquartered in Finland, so kind of much, much smaller, much earliest age organization, but operating in a similar space, you know, cloud computing technology. And we also have a startup program and I work with with startups over at Aiven as well as part of my role.

Melissa 

Okay, what you did a great job summing up a very long story, but you give us all the highlights there. I think I’m sure we could dive into to a lot more kind of details of each of those those phases. But we don’t have time to do all of that today. What I’d love to know is so you haven’t been a founder yourself, but you have worked with a lot of founders and in these different roles you’ve had, what are some of your takeaways with working in these really fast paced roles and organizations and interacting so much with startups?

Ian 

Yeah, I interacted with startups a huge amount when I was at Amazon when I was at AWS and actually, my move into the startup focused role that I had at the end. And in to some extent, it was selfish because I needed to progress at Amazon, I needed to find a bigger job in quotes a job with more scope in order to see myself having myself seen as a candidate for promotion to the next level. So that was one of the drivers. But you know, the second thing that’s an obvious question really is why did I choose startups? There’s lots of big jobs at Amazon. Why did I go after startups as an area of focus? And the answer is simple one, really, I encountered a lot of startup customers at Amazon during my tenure in developer relations and evangelism. And I just loved the mindset, the, you know, the creativity, the vision, the singular purpose that a lot of founders have certainly successful ones, you know, they really understand what the problem is that they’re working on, and how solving that problem delivers value for their for their customers. And I feel really privileged to have had the opportunity to work and encounter a few founders that I think really exemplify that mindset, that sort of problem centric mindspace we solve X for Y is a construct that I’ve encouraged a lot of founders to think about when describing their businesses, because the ones that I’ve seen have been really, really inspirational, and I consider to have been really, really effective can typically articulate that very, very clearly and very, very precisely. So that’s definitely something you know, in my roles, I’ve tended to gravitate certainly of late towards roles that have a heavy communications component, Product Marketing, Developer Relations, and evangelism, they’re all quite similar in that respect. And I really feel that some of the most effective founders that I’ve seen, really have that attribute, they are so clear and precise in the way that they communicate what it is they’re trying to do, and how are they going to take steps towards that goal, that I found that really inspiring and I consider myself really privileged to have worked with and encountered a lot of individuals that I consider to be, you know, really solid leaders, but have been really clear and precise communicators? Most importantly.

Melissa 

Wow, yeah, it does sound like such an interesting role. And to have just so much contact with some of the up and coming startups right in the ecosystem.

Ian 

Yeah, maybe regret actually moving into my last role at Amazon was that I was kind of, you know, a few steps removed from I had a large org, with several 100 people in it in the solutions, architecture space, when I left, and I was kind of removed from the day to day, the opportunity to meet a customer every day or hear from a customer every day, you naturally become at that kind of scale, you’re more focused on mechanisms and approaches that can scale across that team to drive the kind of outcomes that you want, there’s still an opportunity to spend time with customers. But it’s not as much one thing that I really loved about my time in developer relations there as an individual practitioner was actually spending direct time with customers meeting that and meeting them at events, talking to them about what they were trying to achieve, what kind of problems they were trying to solve, I found that really, really fulfilling. And I think that’s a bit of a dichotomy that’s kind of, I think, plagued is a bit of a strong word. But I’ve sort of thought about it a lot throughout my career. And I’m somewhat unusual in that I’ve had periods in my career as an individual contributor and periods in my career as an org leader. And most people that become org leaders don’t actually go back into the IC role, again, individual contributor role again, but I’ve done it a couple of times. And in the main part, it’s been motivated by that desire to get into the detail and, and have an opportunity to figure out, you know, how does what we’re doing as an organization impact individuals and impact customers, and I do really enjoy that I still love things like, you know, fireside chats or interviews with customers that I might get to do as part of an event. I’ve got an off site coming up soon. I’ve been in Helsinki at HQ in February, this year, and I’m really excited to have the opportunity to interview one of Ireland’s largest and earliest customers during that event. I’m really, really looking forward to that opportunity. I think it’ll be great to talk to somebody that’s using our products that’s using our stuff and for whom we’re making a difference. I know, I’ll get a huge amount of energy out of that.

Melissa 

Yeah. What’s so interesting for you to say that it’s something I hear from a lot of founders when their companies scale, they lose this opportunity to have so much of the day to day on the ground interactions with those customers. And so it does sound like it’s a unique thing you’ve been able to find in your career, kind of balancing that piece finding space for it.

Ian 

Yeah, I’ve had a few opportunities. used to do that. And I think now I’ve kind of grown through that I’m confident now that in future roles, I will focus on getting the balance, right and making sure that I don’t lose the parts of the role. But I really, I really enjoy that I really get get, you know, get a sense of fulfillment from

Melissa 

Yeah. Well, Ian, let’s dive a little bit more into the more vulnerable spot of this interview today. I know that you shared with me your Twitter bio. And in that Twitter bio, there is a black heart. I would love if you could share with us more about that, what’s behind that there’s limited characters on that bio. So I know you chose it for a reason.

Ian 

You know, I guess, vulnerability is something that like, I think, like a lot of people I have struggled with, you know, how much do you want to share online, about your own, you know, your own quirks, your own peculiarities, your own vulnerabilities. And that is, you know, an open question that I still feel like, I’m not entirely resolved with an answer for. But I have come to realize, over the years that I consider myself a bit atypical, maybe or unusual. In that I find it often difficult to say that I’m really happy. Whether that is depression, whether that is a kind of, you know, a sense of dissatisfaction, or lack of fulfillment, I feel, it’s kind of hard to pin. But I have thought about that a lot. And I can continue to think about it a lot. But what I’ve also come to realize, you know, and probably have my, you know, internal conversations about a lot is, is there anything wrong with that? Is it necessary for everybody to be happy, smiley and positive all the time? Or do you need to have a mix? You know, is it good to have somebody in an organization that, you know, their core, I’d say, you know, if you want to describe it, and maybe I’m never really satisfied, might be a good way to a good way to characterize it? Is that a valuable trait in a leader. And actually, I think it can be, you know, I’m not afraid to criticize my own work. And actually, Amazon when I joined the changed our leadership principles, while I was that one of the leadership principles that they used to have was vocally self critical, and they took this leadership principle and they rolled it into another one called learn and be curious and became part of became part of their learning be curious leadership principle, essentially saying that by being vocally self critical, you could learn something and seek improvement, you know, but I actually preferred it when it was standalone. And I would say that I indexed extremely highly on that leadership principle, always looking for opportunities to improve and you know, always been open to feedback, even if that feedback looks on the face of brick ridiculous. And I’ll give you an example of where I encountered the second, I would still take it on board and try to act on it. When I was early in Amazon, I was obviously an individual contributor, creating technical content to try to drive awareness of AWS and I did a series created a series of videos, which you can still find on YouTube now. And one of them is actually incredibly popular. I created something called the EC2 masterclass, which is a YouTube video about AWS EC2 service that computing service is garnered hundreds of 1000s of views on YouTube, it’s by far the most popular piece of content that I’ve ever created in my career. And I think part of that was timing, and you know, getting a lucky break with Google’s YouTube’s recommendation algorithm and getting a lot of views. And with views comes feedback. And if you look at the comments on that video, you will literally say, literally see, in sequence in sequence, you talk too fast, you talk too slowly. This video is too high level this video is to detail.

Melissa 

Okay, you got the full spectrum of all everything.

Ian 

You know, I really like even though that sounds ridiculous when you say it because you know, the content creator. That’s the kind of stuff that you have to deal with. Everybody has opinions, right? Everybody wants to share them. But I would sometimes encounter people even in my team over the Amazon working in evangelism developer relations, who would say to discard the feedback if it was critical feedback, and I would say I never ever discard feedback, no matter how critical or personal it is. I always listen to it. And I always listen to then I always try to take action to make improvement even if it seems ridiculous. So yeah, I guess that’s the other side of the, you know, potentially a valuable side of the verbally self critical. I guess I’m down on myself. But somehow I managed to turn that fact that I feel like I’m sometimes down on myself into into something which has enabled me to, you know, in some cases, at least drive good type performance on some of the work I’ve done.

Melissa 

Do you think that there’s that there’s a way that you manage to keep from taking it personally, when you had that feedback?

Ian 

I would say quite the opposite. I take it very personally. But, but for whatever reason, I just seem to be able to plow through it and sort of compartmentalize it or park it and say, you know, it’s, of course, it’s about me, isn’t it? If someone’s criticizing the way you speak, or the way you vocalize, it’s directly about you and your behaviors. So it’s very hard to say that’s not personal feedback. It is personal feedback. It’s how you respond to it, isn’t it? Like, I had a critical comment on one of my videos about inadvertent noises when I speak. So now I have a pop screen in front of my microphone to try and kill them off. And so there are things you can do. And if you think you know, that’s highly personal feedback, it doesn’t mean that you shouldn’t act on it. But yeah, it can be hard sometimes when you’re taking all on board. Yeah.

Melissa 

Yeah, I think it is. For people in a leadership role, right? You’re putting yourself out there for more visibility. And for more feedback.

Ian 

Oh, yeah, you’re putting yourself out there. And if you’re in a highly public role, like a lot of individuals working in developer relations are, you know, I’m not the most public by any means. I’ve got a few pieces of content that have got good traction. I’ve got a couple think 15,000 16,000 followers on my Twitter. So you know, I’ve got a few that you could look across the industry. There’s a phenomenally high impact guy working at a Google called Kelsey Hightower, he’s got almost 200,000 Twitter followers. And it feels to me, like every comment he makes must be under the microscope, but he still does a phenomenal job, you know, and produces amazing work. And I’m sure has contributed to career development for hundreds and hundreds of 1000s of software developers and architects around the world in a really positive way. And he’s way more out there than I have ever been in terms of his public profile. And that is a risk, I guess, that comes with these developer relations, style roles. Your job is to influence your job is to change behavior. And you can’t do that if you’re hiding in a cupboard. You know?

Melissa 

Probably not, unless you have you know, you’re not going to have the same type of impact that you’ve been able to have you been if you have your smartphone in that cupboard with you.

Ian 

So, yeah, put yourself out there as part of the job.

Melissa 

Yeah, you said something so important that I talk with a lot about my, with my clients about is that, yes, you’re gonna get the feedback, you might be under a microscope, but you have to think about the influence that you’re going to make. Like that’s that’s kind of the that’s the reason behind the work that you’re doing right, is to impact those people is to make it make a difference and drive change.

Ian 

Yeah, I mean, we could turn this into an interview about developer relations, which obviously is one of the one of the challenges in my, my specialist area of Dev Rel is impact measurement. You know, a lot of people will, will debate what is the what is the purpose of the developer relations role, but fundamentally, it’s changing behavior, driving aware… increasing awareness, to drive adoption of products and services. And that means changing the behavior of, of developers or other technical end users, getting them to use your your technology and preference to others. So you have to be able to influence to do that. It’s fundamental. It’s a fundamental skill.

Melissa 

Yeah. Well, let’s talk a little bit more about some some of the things that you that you shared with me before we had the interview. I know right, before we pressed record, we were talking a bit about self doubt. You mentioned experiencing self doubt. And we were talking about what is, if self doubt, is always imposter syndrome.

Ian 

I don’t think so. I think that when I hear the phrase imposter syndrome, that what it says to me is, it’s to do with one particular thing, or one particular event, or one particular group interaction, maybe that you’re in as an individual where you feel out of place. So you kind of feel like I don’t deserve this might be the I shouldn’t be here might be the way that I would articulate it. And of course, I felt that and I do feel it. But I wouldn’t say that’s quite the same as self doubt. I wouldn’t say self doubt is much more, my take on it anyway, my experience of it has been a lot more long term. And it’s not necessarily related to any particular activity or thing that I do. I would say it’s a little bit more deep rooted a little bit more ingrained than that in me. Now, which is kind of hard and quite challenging to articulate. Maybe it’s linked to value or worth more than it is to a particular activity that I’m doing. So you know, it’s quite a foundational feeling that I have within me. It’s not really you know, I shouldn’t be doing this role or I shouldn’t be giving this presentation or I shouldn’t be here in this particular meeting or having this conversation. It’s a little bit more fundamental than that to me.

Melissa 

Yeah, Well Ian, I would love to know to, you know, one thing I hear a lot from from founders were people working in startups are just the challenge. Some of the challenges that can come to your mental health are just kind of state of mind well-being when you’re working in these fast paced organizations. Did you find that in any of those roles?

Ian 

I’d say yes. You know, I think in a sense, I sort of went down a little bit of the cultural rabbit hole when I was at AWS. And I’ve talked about those leadership principles and how attractive they were for me when I joined the org. But, you know, towards the end of my time there, I started realizing, and this is not a criticism because I think it’s a great organization. But I started realizing there were like, consequences from some of those leadership principles. Some of them were like, just a organizational outcomes. You know, if you’re talking about ownership, for example, which is one of the the leadership principles that they have over there, Amazon, it also a byproduct of really, really high ownership is lack of coordination or is over there, we’ve got very large org. So you can get a left hand and right hand, you know, not only do they not know what each other is doing a lot of the time, they don’t even know that each other exists, because you’ve got very high ownership individuals focused on the problem right in front of me. So you do get, you know, duplication and rebuilding of the same mechanisms or technologies more than once, which can be a bit frustrating. The other the other thing that’s been quite well documented and talked about a little bit in the media is things like regretted attrition and how Amazon historically have sought to drive some individuals to leave the organization with this idea of bar raising, like removing low performers on a consistent basis and replacing them with with high performing individuals. It happens in a lot of orgs. You know, understand that. That kind of culture originally came from GE in the US, US from General Electric, and it’s been adopted by, by other companies. And in my last role, I was doing that, of course, because it’s required at the level I was at within Amazon. But on the other side, I was also trying to hire like crazy at the same time to grow the org. So you kind of bringing people in and taking people out. I found that really difficult at the end. You know, and it was made more difficult by the circumstances, right, you got to remember the last job that I took at Amazon, I accepted the role in mid March 2020.

Melissa 

We all know what was happening at that point.

Ian 

Yeah, yeah. Oh, you know, I hear so many people sharing stories like that, where it wasn’t just the pandemic, right, there was another type of big life event, tragic life event often that it’s a lot and changing roles. At the same time. It’s a lot to have on your plate. Living in Seattle, you know, moving to Seattle, taking that role moving to Seattle and doing it. A couple of weeks later, I had to go back to the UK because COVID, the waves of COVID was starting to break all over the world, on the economy and on public policy. So I went back to the UK. And then I started that job in well, it should have been the 18th of April, I started it 2020, 3 weeks before the UK went into lockdown, COVID lockdown, and then a week into the COVID lockdown my father passed away completely unexpectedly. He had an undiagnosed bowel cancer. He called me on a Thursday evening to say that Thursday morning to say that he was in hospital. And he was operated on that evening, and he never recovered consciousness and he died on the Friday. So my world was kind of from accepting the role to starting it my role and completely, my world had completely changed. I’ve moved back to the UK, I had a very, very unexpected and shocking loss in my family that I found really hard to deal with. And then I spent the next well months alone in my apartment in the UK. So I had a really, really tough period. And I think that was a big factor in my deciding to move on. I wanted to change, you know, I think it was like, I wanted to change everything. So I’m gonna leave Amazon, I’m gonna take a different role, do something completely different. Thankfully, that summer, I met my new partner. And that was a huge emotional support and actually really helped me get through the pandemic, I think it would have been a very, very tough period, if I’d been genuinely alone for the whole of the period that I was working in that role. It was a very difficult period of my life, really. Well, thankfully, my manager was very, very understanding of the circumstances, Bob called Bob van Nortwick really great guy. He was so understanding of what happened, it really helped me to ease into that new role in a kind of gradual way, which was actually in retrospect, very kind and supportive of him really helped me deal with what was a very challenging set of circumstances really.

Melissa 

Yeah. I’m so curious, because I know we have people listening here who might be facing really difficult person circumstances in their personal lives while you know, growing in their professional role. Do you have any advice for people who are in that position?

Ian 

Well, it’s a really tough one, isn’t it? For someone that is quite solitary, you know, I don’t really have a large circle of friends. In fact, it’s hard for me to really sort of count people I would say my friends very, very, very, very tight in terms of the relationships that I have. I was, and this had been a couple of cases where this has happened and it’s kind of made me feel like I’m not alone. I got a huge amount of positive support and sympathy and warmth I’d say from people that I consider barely acquaintances, people who really kind about my bereavement. And actually when I went on to leave Amazon, you know, I’ve been there for eight years and it was somewhat daunting to move on to another role. And the same, I got a huge amount of support from people that I consider again, you know, in some cases, barely acquaintances and colleagues, I got 1000s of positive comments on my impact over there. So those things really helped me. And I guess that’s the positive side of social media is that I’ve come to really have, you know, mixed feelings about whether or not social media is a good thing. It certainly is highly polarized and can be really divisive. And I think people with vulnerabilities can often have them exposed badly on social media. And this is one of the reasons that I have diminished the amount of activity that I have on public platforms like Twitter, for example, and tried to keep it focused solely on on my work. But, you know, in those two circumstances, I did actually get a lot of support from people on social media networks, and did actually help me so kind of arguing against my own point of view. Certainly something. Yeah.

Melissa 

Yeah, yeah. Well, I guess we can, we can agree there’s pros and cons to social media that you really, you got that sense of connection and support on there.

Ian 

In those two circumstances where I probably needed it most. Yeah, I did. Yeah.

Melissa 

That’s fantastic. Well, one other thing I’m just curious about is in your role, like, in your role, working with startups, is there anything like any thing that you’ve seen in terms of I mean, I hear all the time and I hear in my work, and it’s one of the reasons I’ve created this podcast, is there are so many struggles with mental health and mental well being within the startup community within that fast paced, lots of pressure community, did you see that happening with with your work and supporting the startup system?

Ian 

I think it will be tough for me to say that I’ve seen a lot of instances of it. You know, as a in quotes, vendor, somebody that’s providing technology to companies, you’re not always in right there, are you? You’re at arm’s length to some extent. So it’s a little bit difficult to say that I’ve seen a lot of examples of it, I’ve now got a relationship with a startup where I’m doing an advisory role. It’s a fintech. It’s my first sort of attempt, working with a startup outside of the sort of supplier customer relationship that I’ve been engaged with AWS and Mongo, and now in my new role. So I’ve just got started with that fact, we just had our first Advisory Board meeting earlier this week, and I’ve been working with them for about three months. So I’m seeing a lot more there. And I help them find one of their early one of their early tech hires as well to move into that org. And I suspect that I’ll get to see a lot more of the internals, you know, maybe experienced some of that in this in that role, but I have, of course, you know, in my time at Amazon, I’ve been in really, really high growth, or it’s not a startup in technical terms, but I came to AWS is about the 50th employee that they had in the UK.

Melissa 

Wow. Yeah, right at the early stages.

Ian 

I was really, it was really, really early. They had almost no enterprise customers back then, in 2013, they announced News Corporation and Infor in 2014, when I’ve been there a few months. And that was what I consider to be the sort of touch base for being late on enterprise cloud adoption, really. So yeah. And we had to support each other a lot. Because we were doing all kinds of jobs, you know, within startups and within high growth organizations, generally, role boundaries just don’t really exist, do they? You know, people in the US often say, I’m the janitor, the accountant, the office cleaner, you’re doing absolutely, absolutely everything. And it’s the same in high growth organizations, even if they’re inside big companies, boundaries get blurred. And, you know, you can experience very intense working periods where it feels like you have no life outside of the office, you sort of commit everything to that. And I think one piece of guidance, I would say is, you can do that, okay, but you should always be sure that if you’re doing that you’re conscious of what you’re doing. You know, you’re spending your whole life tipping everything you’ve got into into your work into a company or into your job, then what are you degrading as a result of that? And the answer is probably something and you should certainly think about that.

Melissa 

Yeah, I think that’s fantastic advice. Yeah, just to be very conscious of it, and the possible repercussions that it can have as well, right. It’s not just like, everything’s gonna turn out fantastic when you do that.

Ian 

The older you get, the more you realize that life is just all about trade offs, right. And business actually is very much all about trade offs as well. So if you do X, Y might happen. Just make sure you know.

Melissa 

Exactly. Well, that’s the tough thing about life, right? And you have to go through so much of this stuff to actually have those like that those kernels of wisdom

Ian 

To learn those lessons. Yeah. And you know, in the, we used to joke or AWS, about best practices and how it was better to learn from other people’s mistakes and your own, you know, I’ve been singularly bad at applying that same principle to my personal life, I’ve made a lot of mistakes, and had to learn lessons from them.

Melissa 

Yeah, yeah. I mean, my hope is on this podcast, though, that people are going to listen to some things and you know, listen to leaders like you and to take some of that glean some wisdom from it. So let’s, let’s talk a little bit more about that, too. You mentioned that you have some kind of, you called them low level hacks that you use to help with your mindset. Can you share some of that?

Ian 

Oh, yeah, I mean, some of it’s like, really, really even consider it a little hack, you know, when I used to go on stage a lot at Amazon and give those big public presentations that I used to give. And some of them were big. I remember doing a keynote in Beijing, China with over 5000 people in the audience. And I was speaking in English, and it was simultaneously translated into Mandarin. So it was like, really, really? Yeah, wow, I think it’s the biggest thing I’ve ever done in terms of public speaking. You know, the biggest trick that I have is before you do anything, which is high pressure, or when you’re really, really anxious, and really, really nervous about X, I was really, really anxious and really, really nervous is to stick a smile on your face and grin as hard as you can for 30 seconds. And for whatever reason, it’s like sensory response to that is you’re flooding your body with some kind of brain chemical with the stresses. Yeah. So if you grin, your nerves will just in mind anyway, my nerves just dissipate out. So that’s definitely something that I use. If I’m feeling stressed, or negative, or really anxious, I do feel anxious a lot, then just jamming that grin on my face in private, is actually really effective. And it sounds really stupid. But it really, really works for me.

Melissa 

Oh, that’s fantastic. And I appreciate you sharing with the audience that you know, you you it sounds like that that speech went really well. The presentation went really well. But you were nervous, right? Even though you were willing to take it on. You are nervous. I think a lot of times people think that we have to get rid of that anxiety before we do things

Ian 

You can? Well, I certainly can’t Yeah, you can’t ever completely get rid of it, the trick is being good enough at hiding it. So nobody knows. And I’ve been told many times great presentation, or that was amazing. When I’m giving a talk. Every single time I get those butterflies and I feel like I’m not gonna get as I always go through it, of course, but it’s masking, isn’t it? You know, it’s like hiding that feeling that you’ve got, it’s not gonna go? Well, that’s one thing. And the second thing I was going to talk about here was about feedback. Well, we already talked about that a little bit earlier, you know, when I was talking about those YouTube comments that I used to get. And the fact that, like I said, I’ve heard many people just ignore critical feedback. You know, I really don’t think that’s a good idea. I think you should hear everything and act on the stuff that’s important. And yeah, people will make personal comments about you, they will say that they don’t like the way you talk, it’s very hard to change the way you talk, if you’ve got an accent, or you’ve got interruptions in your speeches I used to have, it takes years of conscious practice to try to eliminate those. But I still worked on it, even though it was hard to hear it and kind of difficult to take. And I consider that I’ve made progress in my public speaking as a result of that. I’m a lot clearer now. And I used to be but it was hard feedback to to hear at the beginning.

Melissa 

Yeah, I’ve heard people describe it as shifting, like sorting through your mail, right? Like, okay, this is junk mail. Like you don’t need to take that feedback. But you can’t just throw all your mail in the bin.

Ian 

No, that will be a really bad idea. There’s probably a bill in there, or maybe a check. You don’t want to do that.

Melissa 

Exactly. Yeah. Yeah. So I hope that people will hear that and, you know, find a way to take feedback that that works for them because it is its data, right? It’s data that you can take and learn from.

Ian 

It is and finding ways to make feedback less anecdotal and more data driven is a really good thing. You know, I mean, always read the comments because the comments are where the gold is often, but it can make it a lot easier to read the comments if you’ve got some quantitative numerical score that you’re using to measure your trajectory as well. So if you get one of those increases of feedback. And I have considered some of them mean over the years. If you’re getting a, you know, 4.9 out of five, Speaker satisfaction score, you weigh that off against the critical feedback that you’re getting. And maybe you don’t need to take it on board. If you’re getting a 2.1, then you’ve got to listen to everything and read everything and try to improve on the narrative feedback, because that’s where the opportunity for getting better is.

Melissa 

And yeah, I would love to know what about some of the successes that you’ve had in your career? What would you mark as the best successes, because that does help our mindset, right? It’s focusing on the good.

Ian 

Oh, yeah, yeah, well, I mean, turning back to what I said about social media, and some of the positive comments that I got, when I leave, when I left, when I left Amazon, when I left AWS to go to MongoDB, there was one thing that really stuck with me. And it was, again, from somebody that I would consider an acquaintance that I’ve met a few times at a few events, but they wrote something that really, really resonated with me, and I can still remember the wording that they use now, which probably indicates quite how much it stuck with me. And it said, think of the impact that you have had, you have made 1000s or influenced 1000s of people in to make them reconsider the way in which they think about technology. And that was from somebody that I didn’t know, I didn’t really know them very well. But what they wrote about me, it really made me reflect on my role. And, you know, of the impact that I had there. Honestly, I believe it was significant because of comments like that, that I received as part of my as part of my transition. So that’s definitely something. And then the second thing is, there are people that I’ve had the opportunity to work with, you know, and I’ve been called a non empathetic leader before, before somebody that doesn’t really know consider or care for the individuals in their team. And probably that feedback has been warranted at the time I’ve been through restructurings to let people go, like any business leader does have had to deal with performance issues, you know, where one set of individuals has not met my expectations or the expectations of the org, and of course, you’ve got to deal with that if long term effects of not dealing with it and much more significant than the effects of taking pain and dealing with it. But weirdly enough, even those those things have been said about me probably fairly, actually consider some of my biggest successes, the trajectories of some of the individuals that I’ve worked with, and some of them as customers. Some of them are team members, for example. There’s the lady and I won’t name her a woman who joined AWS in Africa as developer relations persons shortly after my tenure ended, who previously been a customer. Several years earlier, she contacted me to say I’d like to work in developer relations, what should I do, and I gave her a few ideas of things that she should focus on. And she went on to become AWS, his first black woman, developer advocate located in Africa. And not entirely by following my advice, but in part by following some of the guidance that I gave her, I found that incredibly rewarding and satisfying. There’s a few people in my team have gone on to what I consider to be great jobs. And actually, do I consider my influence to be significant? No, it’s more, I feel privileged to have worked alongside them, and been able to observe some of the great work they’ve done. But you know, obviously, it created an environment as the leader of that function where they could have that success and go on to better things. This person is working for a machine learning startup in France now that worked with me that I consider an amazing developer evangelist, a huge, technologist and incredible in terms of his level of output. So I was privileged to work with him. And the person in the Nordics, who now works on an AWS service team, same thing, he came to my team, very unsure of his capabilities, and actually unsure whether he could be successful in in the role and went on to be a phenomenal success and move on to a very, very senior engineering role elsewhere within Amazon. So no, it’s weird that despite those things haven’t been said about me. I still consider people development and specific examples of people development as some of the things that I’m most proud of in my role.

Melissa 

Yeah, it sounds like you’ve really served the role of a mentor for those individuals.

Ian 

Those individuals I think I did, yeah, yeah. Yeah.

Melissa 

I think we could do a whole show about empathy as a leader, but we will not have time to dive in that to that today. Yet, I would love to know, you already mentioned some words of wisdom for yourself. I did actually want to ask you, what’s next for you in your career after this? You have a lot of roles that you’ve had already. What’s next for you?

Ian 

Yeah, well, I just moved to an organization that’s at a much earlier stage in its lifecycle with Aiven you know, they’re a series D startup headquartered in Helsinki, Finland. We did have about 580 employees, but we just went through a little bit of a force reduction to about to let some people go as part of restructuring exercise. So back down around 450 people now. So that’s very early. And, you know, again, like I said earlier in writing my school bio, which I did quite recently, which is quite a timely, you know, opportunity to reflect, I wrote that I figured out that working with companies and organizations that are a formative stage that are still building that have got a lot of decisions to make, and therefore a lot of opportunity for experimentation of it actually realized of late that that is something that I found find really fulfilling. I like the ambiguity. I guess it’s having experience that I can apply, but uncertainty about how effective that experience is going to be. So it’s not mechanically repeating the same actions over and over again, that idea, it’s a lot more trying to figure out how does my experience apply into this particular problem or this particular challenge. So I’m definitely going to seek opportunities that have that early stage, openness, that kind of breadth of field, that decision making that experimental opportunity within them, and want to do more than just be employed. Like I said, with the with the advisory role that reasonably taken with this Fintech startup, I’d really like to do more of that like to have lightweight advisory roles of that type. Plus my main role at Aiven for the foreseeable future, I feel like that is a good setup for me for the next, you know, maybe 10 to 15 years as I finish up my career.

Melissa 

Yeah, well, I can completely understand that, especially after you were mentioning how rewarding fulfilling it was to have those those mentorship roles, that sounds like a good fit for you.

Ian 

Yeah, enjoy it, I really enjoy it.

Melissa 

Any last words of wisdom that you would give your younger self, actually, if we could go back in time, getting you started off in your career, and maybe when you made that shift to cloud computing.

Ian 

So just be more aware of those trade offs? You know, that’s the key, I think. And it applies all over the place. It applies in your personal life, it applies in business, if you’re going to make a decision, it’s going to have side effects or byproducts. You need to be thinking about that. And maybe I would have had a less turbulent life in some ways, if I’d been a little bit more aware of that, when I was when I was in the formative stages of my career, and that’d be my formative stages of my life as well.

Melissa 

Wonderful. Well, thank you so much, again, for being here today. Where can listeners connect with you?

Ian 

You can find me on LinkedIn. If you look me look for me Ian Massingham. Of course, and you can still find me on Twitter, not that active but you can find me on Twitter. It’s Ian with four M’s after So Ianmmmm. And I’ll say the backstory to that is no more complicated than Ianm, Ianmm and Ianmmm had already gone when I joined Twitter, so I was left with that with four m’s. You can find me there as well.

Melissa 

Wonderful. I will link to those to those accounts in the show notes. Thanks again for having this great conversation with me today. Appreciate it.

Ian 

Thanks for having me. Appreciate it as well. Bye bye.

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HI I’M MELISSA

I’m an executive coach for entrepreneurs who want to make an impact without sacrificing their mental health or relationships along the way.

I'm also a former therapist, host of the Founders' Fears & Failures podcast, and co-founder of the Location Independent Therapists (LIT) Community.

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