This podcast interview focuses on the entrepreneurial journey to build deep vertical business solutions that deliver 10x value for every 1x in price charged. My guest is Dan Uyemura, CEO of Pushpress.

Dan has had an entrepreneurial spirit from a young age. He was a Dot-com era pioneer: During college, he founded Mixture.com, a platform that was ahead of its time and preceded social media giants like Myspace. 

After working in tech, including a stint at Myspace, he made a dramatic career pivot by opening his own CrossFit gym. 

He quickly got frustrated with the poor software options available for gym management.

So in January 2012, he leveraged his tech background to create PushPress and rebel against manual paperwork and complicated, overpriced software.

Their mission: to make gym management
 the easiest part of starting a fitness business. 

And this inspired me, and hence I invited Dan to my podcast. We explore his journey from MySpace coder to gym owner to software entrepreneur. Dan shares his insights on what it takes to create a competitive advantage that's hard to beat. He elaborates on empathy-driven support, value-based pricing, and the "layer cake" approach that makes his SaaS products invaluable. He emphasizes the importance of focusing on customer value over traditional SaaS metrics and shares innovative strategies to outmaneuver competitors. Last but not least, he shares his data-driven decision-making framework and lessons on team building. 

Here's one of his quotes

"Money is an output. It's the result of energy spent somewhere else. So the problem is, a lot of people build those businesses around money. How do I make more money? How do I generate more money? How do I increase my top line? Or bottom line? The reality is that's an output, and you can never affect an output. You can only affect the input. And the input is the order of magnitude and the sheer volume of value you provide to customers. That's what you got to focus on."

During this interview, you will learn four things:

1. How he's tuning his product strategy to grow a highly defensible position against competitors.
2. His framework for building conviction and speeding up decision-making in feature development
3. How he overcame the balancing act of horizontal feature breadth with vertical depth improvements
4. His approach to innovating pricing models to outmaneuver competitors and accelerate growth.

For more information about the guest from this week:

• Dan Uyemura
• Website: Pushpress

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This podcast interview focuses on the entrepreneurial journey to democratize political data and anticipate regulatory changes. My guest is Victor Kristof, Co-founder and CEO of DemoSquare. 

Victor is a fascinating individual with a unique blend of academic excellence, entrepreneurial spirit, and a passion for leveraging technology to enhance democratic processes.

He holds a Ph.D. in Machine Learning from Ecole Polytechnique Federale de Lausanne, where he developed algorithms and statistical models to study human behavior within social and political systems.

That research became the foundational idea behind DemoSquare, a SaaS startup he co-founded in November 2022. 

Their mission: to "democratize democracy" by making political and regulatory data more transparent and accessible with artificial intelligence.

It will change how companies and their public affairs teams navigate the complex world of politics and regulation and, potentially, how citizens engage with democracy.

And this inspired me, and hence I invited Victor to my podcast. We explore the journey of transforming academic research into a change-making political data platform. Kristof shares his lessons learned by doing customer interviews and pivoting in the right direction. He highlights the value of sharing ideas openly, adapting to constant change, and maintaining resilience in the face of rejection. Last but not least, he offers practical advice on investor relationships, sales strategies, and personal stress management. 

Here's one of his quotes

I've heard several times people saying, "I have this super cool idea. I don't want to share it with anyone until I do it. I had the complete opposite experience. Even when it wasn't completely ready, we were not selling it, just talking about it to people, not even in a professional or formal context. You go to a party, you go to a family gathering, and you meet with some friends. You just share your ideas and see what's happening. The most important feedback I got came from these informal discussions. I cannot count how many introductions to potential customers I've gotten through these informal discussions.

During this interview, you will learn four things:

1. How to gather feedback and validate your idea - and use both positive and negative feedback to refine (or even pivot) your product.
2. How finding the right co-founder can have a multiplicative effect on your business.
3. How to stay resilient in the Face of Rejection from both customers and investors.
4. What to look for to select investors who will make a difference for your business. 

For more information about the guest from this week:

• Victor Kristof
• Website: DemoSquare

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This podcast interview focuses on the entrepreneurial journey to help all of us to have conversations that drive action and meaningful connections.

My guest is Joaquim Lecha, CEO of Typeform.

Joaquim (Kim) is a tech entrepreneur on a big mission, bringing over 20 years of experience in high-growth companies. He started his career in M&A, strategy, and financial advisory. In 2012 he joined the tech world as the CFO of Socialpoint, a world-renowned mobile game developer, later taking on the role of Chief Operating Officer.

In 2018 he joined Typeform as Chief Operating Officer and quickly rose to become the CEO. Their mission: to create a world where conversations drive action and meaningful connections. 

Under his leadership, Typeform has grown impressively (+$1B valuation), now serving well over 150,000 paying customers worldwide and achieving profitability. He recently got recognized as one of the Top 50 SaaS CEOs of 2023 by The Software Report.

This inspired me, so I invited Joachim to my podcast. We explore what it takes to profitably scale a SaaS business as it experiences rapid growth. He discusses what fueled their initial growth and what strategic changes he had to make to ensure growth won't stall. Last but not least he offers practical wisdom on product development, customer-centric innovation, and maintaining resilience in the face of challenges.

Here's one of his quotes

I was coming from games. I had not heard from those types of products so many times the word 'Love'. People love Typeform. So my most immediate reaction to all of that is, how can we make more people aware of this great product? 

And I even thought, since I come from a financial type of background; 'if we can find that scalable with quick feedback loop type of motion, and in addition to that, it's got a less than 12 month payback period. Then we can fund it.' 

So with that in mind, we got to work. We grew our customer base by 2.5x and our revenue by almost 4x.

During this interview, you will learn four things:

1. How to ensure your pricing reflects the true value your product provides to customers - so you don't undervalue your offering.
2. How to choose marketing and sales approaches that can bring in thousands of new customers and provide quick feedback loops.
3. How he found a segment in the market where Typeform provided the most value - and what that meant to their growth trajectory..
4. What to focus operations and hiring strategy on - if you aim to create a sustainable, resilient, and easily scalable business over time.

For more information about the guest from this week:

• Joaquim Lecha
• Website: Typeform

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This podcast interview focuses on the entrepreneurial journey to build a successful bootstrapped SaaS company in the highly competitive scheduling software market.

My guest is Bridget Harris, Co-founder and CEO of You Can Book Me.

Bridget has had three distinct careers, showcasing her versatility and adaptability:

She started in the television and film industry. Then, transitioned to politics, serving as a political advisor focusing on constitutional reform and the House of Lords. Her political career culminated in a role as an advisor to the UK Deputy Prime Minister.

Finally, she co-founded YouCanBook.Me, where she now serves as CEO.

Their mission: To provide the best booking experience for businesses' clients and customers. 

Under Bridget's leadership, YouCanBook.Me has achieved impressive growth:

The company has reached $5 million in Annual Recurring Revenue (ARR) without external funding.

That route was a deliberate one. She decided from day one to avoid external funding that might have distorted business priorities, saying "I'd rather make a million dollars slowly than lose a million dollars fast",

And this inspired me, and hence I invited Bridget to my podcast. We explore her bootstrapping journey over the past 12 years. She shares how she's successfully competing in a saturated market against well-funded competitors and tech giants like Google and Calendly. She elaborates on how she's maintaining a customer-centric approach while managing limited resources. Last but not least, she shares insights on how she overcame the challenges of pricing, overcoming feature bloat, refactoring legacy code, and adapting to market change.

Here's one of her quotes

Feature bloat is real. You can say, 'Let's be really generous about our free tool and have loads of features in the free tool.' All you're doing is confusing free users who need a really simple tool and don't want to think because they're not paying for the software. So they just literally want it to work. 

So if you have a problem that your free users can't contact support, it means that your free tool is more complicated than it needs to be. 

During this interview, you will learn four things:

1. How she's aligning her entire team so they deliver on time and grow an eagerness to go above and beyond. 
2. What she learned from refactoring their pricing approach and the lessons nobody talks about is that 
3. How to avoid feature bloat in your development process.
4. What she's doing differently to create the best customer experience. 

For more information about the guest from this week:

• Bridget Harris
• Website: You Can Book Me
• Bootstrappers Manual

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This podcast interview focuses on the entrepreneurial journey from the last 5 years to turn Plum into the best Talent Intelligence solution on the market. My guest is Caitlin MacGregor, Co-Founder and CEO of Plum

Caitlin MacGregor co-founded Plum in 2012 and has been an earlier guest on my podcast (#54 in February 2019). 

She was voted "most likely to save the world" in her high school yearbook, foreshadowing her future as an innovative entrepreneur.

Before founding Plum, Caitlin built two other businesses, which gave her insights into the need for change around talent processes in the age of automation.

Fast forward, she was recently selected for the EY Entrepreneurial Winning Women™ North America Class of 2024, a program that supports high-potential women entrepreneurs.

Caitlin's drive to democratize access to psychometric data so that no one would have to rely on luck for someone to realize their superpower still underpins the core of the company - although how this is brought to market has evolved a lot.

And it's noticed - HR Tech voted Plum the best Talent Intelligence solution in the market in 2023

This inspired me, and hence I invited Caitlin back to my podcast. We explore the journey over the past 5 years. How did the market change in general - in particular in relation to how we attract and manage talent? She also shares what this means to all of us in the coming years. She then drills into how this has changed their priorities around product strategy and Go To Market. As we discuss this, she reveals some valuable lessons learned in product development, positioning, and segmentation, and how her role as CEO changed in this period of rapid change.  

Here's one of her quotes

12 months ago, we were working on how we best resonate. It was really just about how you get to that Aha moment, and it really has nothing to do with the product and the solution. It was really like the Why. Why should you care about Plum? How do we align to a top three boardroom problem? And how do we connect to that strategic problem [....] so we were able to get into a strategic conversation with the right people that had the power to decide to do things differently. 

During this interview, you will learn four things:

1. How Plum expanded from talent acquisition to full employee lifecycle management 
2. What made them decide to bet on Enterprise instead of SMBs
3. What internal capabilities organizations need to develop and prioritize to gain competitive advantage and become the winners of the future? 
4. How her role as a CEO had to change to effectively lead the rapidly growing organization that Plum is today.

For more information about the guest from this week:

• Caitlin MacGregor
• Website: Plum
• Plum Flourish Assessment

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This podcast interview focuses on the entrepreneurial journey to make complex code understandable for business leaders. My guest is Matt Van Itallie, Founder and CEO of Sema.

Matt has a diverse background spanning law, consulting, education, and tech, and he has held leadership roles at edtech and govtech companies like Social Solutions, and PeopleAdmin. 

He earned his J.D. from Harvard Law School after studying history at Swarthmore College. He's also a thought leader on the impact and responsible adoption of AI in the tech industry. This multidisciplinary experience gives him a unique perspective as a tech founder and CEO.

In September 2017, he founded Sema, a codebase scanning tool. 

Their mission: to bridge the gap between the technical and non-technical worlds, particularly in the context of software development.

And this inspired me, and hence I invited Matt to my podcast. We explore how most tech organizations carry more debt in their codebase - and the business risks that brings. Matt shares his vision of how to solve this - in a world where AI-generated code and Open Source are rapidly gaining popularity. He discusses the learning process he had as a founder in creating a singular, non-consensus vision for the company - and how their unusual approach upfront helped them gain deep differentiation and first-mover advantage. 

Here's one of his quotes

What I know now that I didn't know as a baby entrepreneur was there are so many different versions of 'No,'  except 'Here is some money.' Everything else is 'No' 

"I love it. So interesting. I can really see this helping. This is a pain point. Yes, I want to pilot Yes, I want to tell my friends." That's all No. It's all versions of No, except "here is some money."

During this interview, you will learn four things:

1. How he uncovered a new, totally overlooked, target market where his product quickly became mission-critical, rather than a nice to have.
2. Why he's prioritizing building trust-based relationships with key players in the industry and how he's achieving this.
3. What he's doing differently around creating a team that is more than the sum of its parts.
4. His recommendations on choosing your business model wisely. 

For more information about the guest from this week:

• Matt Van Itallie
• Website: Sema

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This podcast interview focuses on the entrepreneurial journey to drive change and adapt as a B2B marketer in an evolving business landscape. My guest is Christian Klepp, Co-Founder of EINBLICK Consulting and Host of the B2B Marketers on a Mission podcast. 

Christian is a global citizen, entrepreneur, podcast host, and B2B branding expert with over 13 years of experience across diverse markets. Throughout his career, he worked with major global brands like Philips, Caterpillar, Samsung, and Logitech. 

He is a true "third-culture kid." He grew up in Austria, the Philippines, Singapore and China - and is currently living in Canada, giving him a multicultural perspective and ability to bridge East and West.

In 2019, Christian took a leap of faith and co-founded his own B2B branding and marketing consulting firm called EINBLICK. He's also the host of the popular "B2B Marketers on a Mission" podcast, where he interviews talented professionals in the B2B space and provides a platform for sharing cutting-edge insights with the B2B community.

Being a regular listener of his podcast inspired me to invite Christian to my podcast. We explore why marketing isn't optimally leveraged inside many B2B SaaS companies. He shares insights from well over 100 podcasts on what marketers should do differently to increase alignment and buy-in across the organization to make a larger impact. Last but not least, he explains how to avoid complacency in marketing and how, by leveraging different perspectives, the company can stand out more and increase resilience to adapt faster to market change.

Here's one of his quotes

The way that marketers need to deal with addressing buy-in is they need to understand how their organization works. How does your company generate revenue? Where is the most revenue coming from? Which industries? Which customers? Do you understand what EBITDA is? Because if you don't understand, you better start learning about it quickly because that's what your board cares about.

During this interview, you will learn four things:

1. How to turn marketing into a core driver for the business. 
2. How to get insights that matter beyond just interviewing customers.
3. How to approach podcasting strategically, get instant value, and what to prioritize first to get going.
4. How to go about analyzing competitors' strategies to further strengthen differentiation.

For more information about the guest from this week:

• Christian Klepp
• Website: EINBLICK
• B2B Marketing on a Mission Podcast (Spotify / Apple)

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This podcast interview focuses on the entrepreneurial journey to empower business users, especially in SMEs, to easily find insights in their data without technical complexities. My guest is Thomas Wulff Wilhelmsen, Co-founder and CEO of Less.

Thomas and his co-founder Daniel previously worked as consultants in the data space before founding Less. Their experiences and frustrations in this role inspired them to create an analytics product for people like themselves.

And that led to the birth of Less in September 2022. The name "Less" embodies their goal of stripping away complexities to build a product that focuses on the end goal and takes care of the technical aspects behind the scenes.

Their mission: Set doers free to do what they do best: Roll up their sleeves and solve problems. 

And this inspired me, and hence I invited Thomas to my podcast. We explore what's, after decades of development, still broken in the Business Analytics solutions market. Thomas shares his lessons learned from steering Less' journey as a customer-funded startup. He shares how he got early traction with paying customers and how he's creating a culture of analogical thinking to solve problems in creative ways.. Last but not least, he'll inspire you with his fresh perspective on crafting a compelling narrative that sells. 

Here's one of his quotes

"We've been focusing more on the persona than on the sector or industry. We call them doers. People that are curious by nature, that are frustrated with being dependent on other people and want to build cool things that they can show to other people in their teams and drive that change internally."

During this interview, you will learn four things:

1. Where he finds inspiration from taking Storytelling for his business to the next level.
2. What he's done differently from the start to get traction and stay in control as the business grows. 
3. How he ensures everyone understands what's important, and does the right things right to create fans from the start.
4. Why he embraces being "customer funded" rather than just bootstrapped.

For more information about the guest from this week:

• Thomas Wulff Wilhelmsen
• Website: Less

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This podcast interview focuses on the entrepreneurial journey in identifying an emerging opportunity and building an innovative, fast-growing company that transforms how we shop online. My guest is Angelo Coletta, CEO and Co-founder of Zakeke.

Angelo is a serial entrepreneur who has founded and exited multiple companies. 

In 2017 he co-founded Zakeke, an AI Visual Commerce platform. It's doing groundbreaking work in transforming the B2B customer journey and shopping experience. With this focus, it's now  serving 10,000+ eCommerce brands worldwide across 400+ industries

Their mission:  To improve the industry's environmental footprint through the use of technology in the display process, the shopping experience, and the purchasing experience.

And this inspired me, and hence I invited Angelo to my podcast. We explore how the shopping experience is still broken today - and why. Angelo shares his how he's building an organization to fix this and shares anecdotes about his lessons learned in choosing the right team, fostering a culture of innovation, and setting ambitious long-term goals. He then elaborates on creating resilience across the business, customer-centric product development, and how strategic acquisitions and investment in eco-system helped to scale their business.

Here's one of his quotes

I wanted to create a company that was totally based on a long-term vision. This is one of the most difficult choices to make when you start because it means you burn more money in the first years of the company. My opinion is that if you don't start as a long tail business, it's difficult to transform a company with 200 or 300 big customers into a company able to serve 1000s of customers, maybe most of them small customers.

During this interview, you will learn four things:

1. Why have a global mindset from day 1.
2. Why focus on product excellence first before you consider a marketing push?
3. What Angelo specifically prioritizes when it comes to hiring the right people that will help the company grow in good and tough times. 
4. The strategies he applied to establish trust and leverage their growth opportunity via the e-commerce ecosystem. 

For more information about the guest from this week:

• Angelo Coletta
• Website: Zakeke

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This podcast interview focuses on the entrepreneurial journey to make social a positive place again - for everyone. My guest is Matthew McGrory, CEO of Arwen AI.

Matthew is a tech- entrepreneur on a big mission. He has held tech leadership roles: IT Director at Logicalis, Director Managed Services at Acora, and Managing Director at Carrenza (a cloud service provider acquired by Six Degrees Group), 

In the period from July 2018 and September 2020 he took a break from his corporate life to become a House Husband. In that period he developed a passion for using AI to drive positive change.

That led him to cofound Arwen AI in September 2020. Arwen AI is a platform that helps its customers actively moderate and manage their community, across both paid and organic.

Their mission: to make social media a more positive place by filtering out hate speech and toxicity. 

And this inspired me, and hence I invited Matthew to my podcast. We explore what's broken in today's Social Media world. Matthew shares his vision to make Social a place without toxicity and spam. He then elaborates on his hard-won lessons from his journey to speed up direct sales and benefit from using ecosystems to grow even faster. Last but not least, he shares his framework to increase resilience across the organization. 

Here's one of his quotes

I thought, 'This is great, we'll create some technology, fix the problem and everyone will buy it.' I was so wrong on that part. I got to about demo number 200, it was with a US broadcast news organization. And the head of digital said, 'Listen, I'm protected by the First Amendment, I can let anything go up on my channels. I don't have to get rid of it. You're giving me an extra job to do. An extra cost. Tell me why this is valuable to my business. Tell me how it makes me money or saves me money.'

During this interview, you will learn four things:

1. How he gained traction in a market where customers resisted to buy because they saw the solution as an extra job and an extra cost. 
2. What he did differently to gain technical and commercial momentum.
3. What he invested in early on to get access to strategic accounts and speed up the commercial contracting process in enterprise sales situations.
4. How he goes about to keep the business humming, and keeping everyone aligned and motivated - especially in tough times.

For more information about the guest from this week:

• Matthew McGrory
• Website: Arwen AI

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This podcast interview focuses on the entrepreneurial journey to take GTM efficiency to the next level for enterprise SaaS companies. My guest is Josh Ellars, CEO of OpenGTM.

Josh has over 15 years of experience leading successful go-to-market (GTM) functions at high-growth SaaS companies like Metalogix, Qualtrics, and OpenGov. This extensive background gives him unique insights into scaling SaaS businesses.

In 2021 he founded Patri, which was rebranded OpenGTM in 2023. OpenGTM is platform to create content buyers love, capture high-intent leads, and uncover the truth behind your buyers and pipeline. 

It's mission: to unite sales, marketing, customer success, and product around the attributes of highly-retained customers in order to boost revenue and retention.

And this inspired me, and hence I invited Josh to my podcast. We explore what's broken in today's world of Go-to-Market (GTM). Josh shares his wealth of experience in scaling SaaS businesses. He emphasizes the importance of the "sell, design, build" methodology, where market demand pulls product development. He also explains, how their approach helps companies cut through the noise of the crowded go-to-market tech landscape. And last but not least he shares some big lessons learned on differentiation and growing efficiently.

Here's one of his quotes

Too often in Go To Market and in company building in general, we're driven by product market fit. And that's wonderful. But a big portion of that is really identifying: Is there security and regulatory fit? Is there a financial fit? Can we get some sort of return out of this investment we're making in this customer? And I absolutely saw that I had to learn the hard way and lose some very large deals. That got me thinking that I think there's a better way to to vet these opportunities. 

During this interview, you will learn four things:

1. What B2B SaaS companies should look for beyond product-market fit to grow more efficiently.
2. Their framework that drives product strategy in order to build remarkable products. 
3. How they avoid getting caught up in tech-stack rationalization. 
4. How to expand market scope gradually while maintaining a narrow focus on the ideal buyer profile. 

For more information about the guest from this week:

• Josh Ellars
• Website: OpenGTM

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