Tech Entrepreneur on a Mission Podcast
Tech Entrepreneur on a Mission Podcast
Evergreen Podcasts
Welcome to the Tech Entrepreneur on a Mission podcast. My name is Ton Dobbe. I am the founder of Value Inspiration and the author of ‘The Remarkable Effect’. I envision a world where every B2B SaaS business succeeds because they're creating software their customers would miss if were gone 𝗛𝗲𝗿𝗲'𝘀 𝘄𝗵𝘆:  Research consistently shows 90% of all startups fail. That's bad.  What's worse however is that +75% of SaaS Scaleups fail - companies that are supposed to have product-market-fit. Far too few Scaleups create the traction they aspire for and fail for the wrong reasons I believe this should stop - and hence I started my business and this podcast The goal I have with this podcast is two-fold: to inspire new forms of value creation by sharing compelling ideas and stories about the potential we can unlock when technology and people blend in the right way. Share experiences from tech entrepreneurs like you about what it requires to create a remarkable software business and how to overcome the roadblocks to do so.
#290 - Joe Lewin, CEO Foundy - on enabling life-changing moments in SaaS
This podcast interview focuses on product innovation that has the power to buy and sell SaaS businesses in less than 30 days. My guest is Joe Lewin, CEO Foundy.  Joe Lewin is a two-time SaaS founder who successfully sold his first business in 2022. Since selling his company, his vocation has been to modernize the antiquated M&A process for other tech founders.  The demand for a modernized exit process has been accelerated by the turbulence in the tech sector and the broader economy, especially now that it's become harder to raise funding. However, founders face a bottleneck issue because most investment banks and advisory firms primarily focus on serving the most prominent companies (i.e. £15m + in revenue). Foundry is focusing on the bottom 90% of companies. And this inspired me, and hence I invited Joe to my podcast. We explore what's broken in the SaaS M&A market. Joe shares his vision and the change he's committed to creating. He talks about the fundamental decisions he made and the mindset he follows to create a business that lasts. He elaborates on his learnings on how they created early momentum - and how that's now accelerated through word of mouth. Last but not least he shares what he learned from the mistakes he made in hiring Here's one of his quotes I've met hundreds and hundreds of founders now, even those that may raise double-digit VC funding, and a lot of them really do not have the knowledge or insight on how to maximize their valuation upon an exit. And they haven't laid the foundations to build that deep-rooted value During this interview, you will learn four things: Why community-led growth is underrated - especially as a way to get people committed and create viral benefits. The viability of your SaaS business isn't what you say yes to, but who you say no to. The sticky part of your SaaS business doesn't necessarily have to be the product you create. The value your customers love you for isn't often coming from the software but from the life-changing moments. For more information about the guest from this week: Joe Lewin Website: Foundy Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
Nov 28, 2023
40 min
#289 - George Huff, CEO Opal - on reinventing his SaaS business.
This podcast interview focuses on product innovation that has the power for marketing teams to work better together. My guest is George Huff, CEO of Opal. George has been a business/tech/design geek for a long time. That's manifested in a career that started as a web designer and has culminated in him being the co-founder of a few really great companies. In October 2011 he became the CEO of Opal, a platform Built for Marketers Their mission: To enable marketing teams to spend less effort maintaining internal alignment and more time doing the work that matters. George led Opal till July 2016 - stepped down as the CEO - to then take back the scepter in January 2021.  And this inspired me, and hence I invited George to my podcast. We explore the 12 year journey of Opal and what have been the fundamental choices to grow the business to where it is today. We discuss the lessons he learned from stepping down as the CEO - seeing things from a different perspective - and what that meant when he took on the CEO role again halfway the pandemic. He also elaborates on the challenges he faced managing two innovation S-curves in the business. Last but not least he shares his secret to create a business people want to fight for. Here's one of his quotes As a startup person, you had an initial jump, and your ego is like, 'Yeah, we could do anything, we're so great.' The idea of a slowdown is not even in your mind at all. And so, there's a lot of hubris that happens when you craft all these parts of your product, they are your darlings, and then you have to kill them in order to get to the 'What's next'. You've got to admit failure first. During this interview, you will learn four things: The one thing George tests every time to know they're making the right product strategy decisions  How the pandemic - and NOT being in the CEO seat gave him the clarity it was time to reinvent themselves. What George learned from managing the company through a period of two overlapping S-curves - and what he'd do differently next time. What signals to watch for to uncover 'the rotten core' problem and realize you've entered a dead-end road. For more information about the guest from this week: George Huff Website: Opal Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
Nov 21, 2023
40 min
#288 - Jon Ricketts, CEO of Writerly - on building defensible differentiation.
This podcast interview focuses on product innovation that gives creators the power to supercharge their productivity. My guest is Jon Ricketts, Co-founder and CEO of Writerly. Jon's career in the SaaS industry spans over 12 years. He has established himself in the field of artificial intelligence and business innovation. Jon’s journey as an entrepreneur began as an early employee at Transcard, a pioneering fintech company specializing in payment processing.  In June 2022, he co-founded Writerly, which he leads as the CEO.  Their mission: to make it easy for creators – both individual and enterprise – to leverage sophisticated AI to supercharge their productivity.  And this inspired me, and hence I invited Jon to my podcast. We explore what it takes to build a successful Generative AI startup in a period where a tsunami of companies is coming to market every single day. Jon shares how he started the business without a clear idea of what problem to solve and how he found his sweetspot. He then elaborates on what techniques he uses to build defensible differentiation and stand out in the market. Last but not least, he shares his secrets on how to stay nimble as the business grows. Here's one of his quotes The hardest part about being in a generative AI market and seeing the tsunami of companies that are being released is just simply being patient. You try to weaponize speed, speed in terms of development, speed in terms of commercial marketing and sales. But the faster you move, the further back you fall.   Because when you see something that you would like to replicate this week. Well, by the time your engineers and developers have completed, you've done your testing, and you're moving from staging to production, guess what's happened: someone else has come out and made that essentially obsolete. During this interview, you will learn four things: How being intentionally patient can become your biggest value driver in a crazy Generative AI market. Where Jon is looking for signals on what to build and how to sell. How Jon found his sweetspot - even though it didn't look attractive at all. How to design your business intentionally to create defensible differentiation. For more information about the guest from this week: Jon Ricketts Website: Writerly Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
Nov 14, 2023
47 min
#287 - Melissa Kwan, CEO of eWebinar - on living the Bootstrapped SaaS dream.
This podcast interview focuses on product innovation, that has the power to run hundreds of engaging webinars without having to be there. My guest is Melissa Kwan, CEO of eWebinar. Melissa is a 3rd time bootstrapped founder. Her previous company, Spacio (real estate tech), was acquired in 2019. eWebinar was the product she always dreamt about because she was drowning in sales demos, onboarding and training webinars every day for 5 years. So, in March 2019 she made the jump and founded the eWebinar.  Her mission: to give people their time back so they can do something else more fun because that's what life is about. We don't need to work harder; we need to work more creatively. And this inspired me, and hence I invited Melissa to my podcast. We explore how she built a $1M ARR business from scratch - deliberately going the bootstrapped way. Melissa elaborates on her experiences in building software that helps her customers provide experiences that their customers love to engage with. She talks about how getting her first 200 customers was easy but how growing beyond that became a big challenge - and how she overcame that. Last but not least, she shares some of her secrets to creating a SaaS business without getting into the vicious cycle of desperately chasing funding. Here's one of her quotes: The toughest nut to crack is not getting it launched and adopted with your first 200 customers. The toughest stuff to crack is what happens after you've exhausted your entire network and their friends.  That was a huge reality check for me. Because that didn't happen until about a year after launch. Because all I know is sales I didn't realize that what I need for this business is marketing. During this interview, you will learn four things: Why she's (being an automation-passionate) is betting on SEO and LinkedIn content creation instead of cold outreach automation? What's her secret to creating predictable traction (knowing there are no shortcuts)? How doubling her prices became a blessing for her business in many different ways Why she'd opt for bootstrapping her company again if she'd had the choice again? For more information about the guest from this week: Melissa Kwan Website: eWebinar Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
Nov 7, 2023
51 min
#286 - Yoav Vilner, CEO of Walnut - on creating a new SaaS category
This podcast interview focuses on product innovation that has the power to create interactive and personalized product demos that prospects will love. My guest is Yoav Vilner, Co-founder and CEO of Walnut. Yoav is a remarkable tech entrepreneur. He was the founder of one of the world’s first tech marketing companies that helped 600 startups grow and a founding CMO of an anti-bullying startup.  He has been active as a startup mentor with accelerators by Microsoft, Google, Amazon, Yahoo, and the U.N. and as a writer for top outlets such as Inc Magazine, Forbes, CNBC, Entrepreneur, and more. In August 2020, he co-founded Walnut - which he leads as the CEO.  With Walnut - they pioneered a category that enables sales pros to deliver interactive and unbreakable product demos.  Then they launched a movement for prospects that had to suffer through frustrating sales processes that took forever.  And then reinvented SaaS sales - by enabling interactive product demos that focus on value at any stage of the sales process. Their mission: To solve the pain of buying software and create a way for prospects to fall in love with your product. And this inspired me, and hence I invited Yoav to my podcast. We explore the journey of a startup that rapidly gained traction in the market. Yoav explains why he prioritized brand building from day one and how that helped them differentiate themselves in the saturated sales product market. Last but not least, he elaborates on the power of creating a movement - not only incorporating your ideal customers - but also their ideal customers.  Here's one of his quotes Every time that we're working on a new video, we say, 'Let's just push it and see if people are sick of it.' It just helps us tell the story in a way that no other company is able to do it. And so every time we push the limits and boundaries, we just find out that the experiment has been successful. During this interview, you will learn four things: That you can capture immense value from the market even at the MVP stage. How you can get potential customers to commit before you've even fully explained your product Yoav's lessons about how he leveraged external funding in a way that only created winners. Why they took an aggressive approach to show as little as they could to prospects - and why that paid off. For more information about the guest from this week: Yoav Vilner Website: Walnut Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
Oct 31, 2023
35 min
#285 - Doug Camplejohn, CEO at Airspeed - on creating magic moments
This podcast interview focuses on product innovation that has the power to improve your team’s happiness, engagement, and collaboration. My guest is Doug Camplejohn, CEO at Airspeed. Doug Camplejohn is a Tech-Entrepreneur on a Mission. Before his entrepreneurial ventures, he was VP of Marketing and Product Management at enterprise (Epiphany), security (Vontu), and consumer (Apple) companies. Then he founded and and became the CEO of three startup companies. Myplay, who got acquired by Bertelsmann. Mi5 Networks, which was acquired by Symantec. Finally, Fliptop, which was acquired by LinkedIn. In January 2020, he left LinkedIn to become the EVP and GM of Salesforce Sales Cloud.  In July 2021, he founded Airspeed, a suite of Slack and mobile apps that provide fun and simple ways to connect with your teammates. Their mission: to help employees feel connected and celebrated And this inspired me, and hence I invited Doug to my podcast. We explore what's broken in the way businesses build culture in a remote-first world. Doug shares his vision of how to fix this by means of technology - creating an operating system for culture. As we discuss his journey, he explains what early decisions had been fundamental to avoid having to do a complete rebuild when his product hypothesis appeared wrong. He also dives into how he arrived at the perfect shipping cadence for his business and his customers, and how he embraced a language to encourage everyone to push the art of the possible. Last but not least, he shares their approach to creating momentum by leveraging customer stories. Here's one of his quotes We've seen tremendous traction, thousands of companies, and tens of thousands of users on the apps in the first few weeks.  It's all about this understanding that employee connectedness is either the number one cause of retention if you're happy and you're really feeling connected to the team and the mission, or the number one cause of unhappiness and people departing when it's not. And so this is really about reinforcing that. During this interview, you will learn four things: How do you build tremendous traction at the launch stage of your SaaS product Why you should be firm on the destination but flexible on the path. Why everyone should be involved in product - not only the product department - and everyone should be looking at the metrics. How to accelerate  growth by leveraging tech to serve product-qualified leads to Sales For more information about the guest from this week: Doug Camplejohn Website Airspeed Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
Oct 24, 2023
45 min
#284 - Josh Haynam, CEO Interact- on building a SaaS business that customers love.
This podcast interview focuses on product innovation that has the power to increase your business visibility and tap into viral possibilities. My guest is Josh Haynam, Co-founder and CEO of Interact. Josh Haynam is a life-long entrepreneur, having started his first company at the age of 15 and never held a full-time job outside of entrepreneurship. In June 2014 he and his co-founder started Interact a company that's all about connecting brands and customers at a human level They bootstrapped the company up to this point, and have helped more than 150,000 customers generate over 21 million leads and counting for their businesses. Their mission: to empower digital entrepreneurs, creators, and brands to grow their business through empathetic listening, deeper understanding, and true connection. And this inspired me, and hence I invited Josh to my podcast. We explore his bootstrapped journey and the critical choices he and his co-founder had to make along the journey. Josh explains how he's been able to create defensible differentiation from the start. He shares his big lessons learned to accelerate profitability. Last but not least, he explains how COVID led to a big spike in revenue, that quickly became the worst thing that could ever happen to his company - and the counterintuitive thing he's done to come out stronger. Here's one of his quotes There's always this difficulty around like, we could go faster, or we could build more or we could compete better if we were to have funding or if we would just be able to hire these people.  What I always end up remembering is: There are no shortcuts. We're seeing now a lot of our competition shedding users, because they acquired them in a way that wasn't profitable. And so now they have to get rid of them. And that's just like doubly wasting money because it costs money to acquire that user. And then they're also going to be a detractor for your business. It doesn't actually work. It's just really tempting. During this interview, you will learn four things: What to stay true to when you want to build a SaaS business that lasts. The power of credibly detracting customers you don't want. What to do when you're overwhelmed by a flood of better-funded competitors. His tips about the best way to build marketing that works For more information about the guest from this week: Josh Haynam Website Interact Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
Oct 18, 2023
44 min
#283 - Joel Stevenson, CEO of Yesware  - on competing in a dense market
This podcast interview focuses on product innovation that has the power to enable Sales Teams to do meaningful email outreach at scale. My guest is Joel Stevenson, CEO of Yesware. Joel loves building businesses and has 20+ years of experience doing just that. He built a supply chain business from $2MM to $30MM, a B2C eCommerce business from $50MM to $100MM, and a B2B business,  from scratch to several hundred million. He earned a BS from the University of Illinois at Urbana-Champaign and an MBA from Yale School of Management. In March 2017, he joined Yesware as their SVP of Sales & Marketing. He then transitioned into the COO role - and today, he's the CEO. Their mission: To help sales professionals deliver positive buying experiences and build the valuable relationships their customers deserve. This inspired me, and hence, I invited Joel to my podcast. We explore Joel's journey with Yesware and the challenges he had to overcome growing it in an extremely dense market with many better-funded competitors. We discussed how he'd carved out his niche and what that meant for product strategy, marketing, and sales. Joel then elaborates on how a rise in prices during COVID-19 had an unexpected positive effect on the overall quality of the business. Lastly, we discuss the effects of the merger with Vendasta.  Here's one of his quotes A lot of our early value as a company was driven because we have a very good Salesforce integration. But the peril with that strategy was that with Salesforce as a system of record, we're effectively putting all of our data inside of Salesforce.  And then if somebody decides that they're unhappy with Yesware, for whatever reason [...] it doesn't end up becoming that difficult to switch.  And so I wish we would have done earlier what we're doing now - is completing the story where Yesware becomes more of the system of record. I think that would have massively increased our stickiness. The promise of product-led is easy acquisition. The peril of product-led is retention. And that was the thing that we had to keep working on. During this interview, you will learn four things: How you can create meaningful differentiation in an extremely dense market  The true value of your saas is often about what you offer, but how and where you offer it. It's all about context. How one simple (but controversial) change can help attract much better quality customers The power of reflecting on the potential of the success of your SaaS business - and taking an open mindset (without ego) on how to achieve it. For more information about the guest from this week: Joel Stevenson Website Yesware Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
Oct 11, 2023
40 min
#282 - Stijn Hendrikse,  Author T2D3 - on scaling a B2B SaaS business
This podcast interview focuses on the art of successfully scaling a B2B SaaS business. My guest is Stijn Hendrikse, Author of T2D3.  Stijn Hendrikse is a serial entrepreneur and author and has been a growth leader with over 20 years of experience in both SaaS and AI industries. Early in his career, He was a GM at Microsoft and then served as CMO and CEO for multiple B2B SaaS companies, including MightyCall and Acumatica.  Then he founded Kalungi, a growth-as-a-service provider, and wrote T2D3 (Triple, Triple, Double, Double, Double), a book on how to scale SaaS businesses after finding product-market fit. And this inspired me, and hence I invited Stijn to my podcast. We explore the big lessons Stijn learned in growing a range of B2B SaaS businesses - and dig into the typical mistakes companies make trying to scale their business too early, too fast. Stijn discusses his 10-step framework to measure whether you've received product market fit and shares his assessment technique to understand whether a SaaS company has future potential or not. Last but not least, we discuss the art of segmentation, particularly if you're addressing a totally new market. Here's one of his quotes If you're a CEO or founder, it's your number one job to answer two questions. Who's it for, and what's it for? What's the value proposition that you're bringing to the markets? And why is that important for the people that you're trying to serve? You cannot delegate those two questions to anybody else.  And a great way to test your theory: if you're unable to articulate that in some content, either a podcast episode like this or in a blog article, you're really not ready to scale your company. During this interview, you will learn five things: What's the most important indicator of long-term success for a B2B SaaS company?  The 10 steps to measure whether you have product market fit - or not. Three of most important questions a B2B SaaS CEO needs to answer after finding product market fit. The three things to nail if you're looking to attract investors for your SaaS business How to go about segmentation if there's no market yet For more information about the guest from this week: Stijn Hendrikse Website T2D3 10 steps to measure product market fit Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
Oct 3, 2023
47 min
#281 - Kelsey Bishop, CEO Candor on making the dreams happen
This podcast interview focuses on product innovation that has the power to put your team culture on autopilot, share authentically, and discover how to work better together. My guest is Kelsey Bishop, Founder and CEO of Candor. Kelsey is a tech entrepreneur on a mission. She started her career as an employee in early-stage startups. She is also an angel investor in companies that include Primer, Roster, Alongside Finance, Noula Health, Candid Health, Taiyaki, Areyo (acq. Zillow), and Channeled. Throughout her career, she worked on teams that felt like magic and worked on teams where that wasn't the case. Curious as she was, she started digging into why that was the case.  But getting visibility on how a team really works together is hard. Tools like LinkedIn and Glassdoor are cluttered with spam, virtue-signaling, and fake or toxic profiles. So, without finding a solution, she decided to create one herself and founded Candor in May 2021. Their mission: help people find belonging at work. Candor believes true job satisfaction in tech comes when you can be yourself in a team where you are included and accepted. And this inspired me, and hence I invited Kelsey to my podcast. We explore what's so hard about qualifying cultures inside organizations. Kelsey then shares the steps that were critical on her journey to get the company off the ground without a tech team and obtain the funding to accelerate its growth. She then elaborates on what she did differently to make users come back every single day to build the culture they desire. Lastly, she explains how she's able to grow the business without spending anything on marketing - purely leveraging the remarkable effect. Here's one of her quotes We're building some of those tools for day-to-day culture. What we hear from users is, 'A profile is great for onboarding or for this one moment, but company culture happens every single day. And so candor actually can help you manage how you celebrate your people, how you do retros, how you do one-on-ones. All of these moments that require intentionality. And on the flip side, startups usually get them wrong. They're not thinking about this stuff every single day. And when you don't think about it, you usually let it fall by the wayside, and you get it wrong. During this interview, you will learn four things: You can start a successful Tech Startup and your first raving fans without a tech team. Delivering your promises to investors is about doing what makes value sense to your customers and the business - even if this means delaying or even abandoning the original vision you promised them.  Finding your sweetspot starts with finding the people that care about the same.  The reason why people fall in love with your product is not what it does but how it will make them feel.  For more information about the guest from this week: Kelsey Bishop Website Candor Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
Sep 19, 2023
39 min
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