How do you scale your company to millions and billions in ARR? Well, if you ask your average founder or a VC, there are a couple of steps one must take to quickly scale the business after finding the product market fit.

On the other hand, some founders don't take the usual route but rather build their company over time — often bootstrapping and investing the profits back into the company rather than raising money and aiming for an exit a few years down the road.

One such company is Doist which is behind a popular productivity app called Todoist. Recently, we had the chance to talk to its founder and CEO, Amir Salihefendic, about his experience with scaling the product to 30+ million users while being a remote-first company that doesn't share the usual Silicon Valley values.

Throughout the talk, Amir highlighted how persistence and passion for the product pushed him and the team to deliver value for such a long time. He admits that initially, he only wanted to create a side hustle that generated a couple of thousands of dollars. However, after seeing how users loved the product and how passionate they were about it, he knew that he had to scale the operation.

Still, Amir opted for bootstrapping the company and growing it moderately — only hiring when there was a real need for a new role. Being an asynchronous organization long before work-from-home became a thing during the pandemic, our guest admits that the competition was fierce during the year 2020. Still, since every major tech company is pushing for a return to the office, things have returned to normal with Doist maintaining its reputation among remote-first companies.

Amir was open about the leadership challenges of a bootstrapped company, but he also noted that he firmly believes in sustainable growth and wealth distribution — creating more financial options for the company's employees, who are its backbone.

***

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***

Timestamps:

00:00 - Intro
00:36 - What is the episode about?
01:48 - Growing for 20 years
05:26 - What is CEO's job?
08:19 - Being a good communicator
11:02 - The benefits of writing
14:00 - Stock options for employees
16:33 - Not going for the VC money
18:15 - Sharing the wealth with people
19:29 - Remote first culture
21:41 - Saying NO to meetings
24:55 - Building trust with the team
26:48 - What is a CALM company?
28:29 - You need to shut off
33:49 - Lessons from challenging periods
35:58 - Marketing for 30+ million users
38:57 - Creating unique product
43:06 - Find people that care
46:52 - What is the end game?

"Most people don't get into entrepreneurship because they are passionate about accounting" — says Alex Wheldon, co-founder of Rho Banking, a New York-based technology company that raised 350 million dollars to disrupt the business banking sector in the United States.

Still, it goes without saying that even if you have the best possible product out there, your company has to be good at managing money. Otherwise, you might go down faster than you think. That is the exact reason why Rho Banking was founded by Alex and his co-founder Everett Cook, who grew it into one of the most well-respected fintech scaleups, which is now valued at almost half a billion dollars.

We caught up with Alex during his recent visit to Belgrade, Serbia, where IBB and Mia Biberovic had the opportunity to talk about his beginnings in music production and advertising to becoming a serial entrepreneur with a knack for innovation in the regulated industries.

"I truly believe in challenging conventional solutions and seeing the potential to solve fundamental financial management problems for businesses", said Alex who revealed that he wasn't initially interested in finances, but he learned through experience that managing cash flow and maintaining financial discipline are crucial to sustaining and growing a business.

"Rho, in a way, reflects this philosophy by aiming to simplify and enhance financial operations for businesses".

Our guest explained why Rho is not a bank, but is offering banking services and partnering with banks that are more inclined to offer traditional services such as lending and are not focused on the technology part. That is exactly the gap that Rho is filling in, with Alex explaining how their products are helping various businesses across different industries manage money more effectively — from early startups to well-established companies.

Despite his background in advertising, Alex uncovers why Rho is deeply focused on referrals for customer acquisition and not ads. He firmly believes that this approach allows Rho to maintain a close connection with customer needs and refine the product based on feedback. He also reveals how the company fundraised all the way to Series B and how his experience from the dot-com boom helped him deliver a greater value to investors.

***

Engage with your customers over WhatsApp, SMS and iMessage – just like Uber, HubSpot and Meta → bit.ly/44xYxqy

***

Timestamps:

00:00 - Intro
00:42 - What is the episode about?
01:54 - Not a bank, but...
03:15 - Musician with a knack for advertising
05:39 - Don't be foolish with your (company's) money
07:34 - The rule of First Principles
09:13 - Who are Rho's customers?
12:00 - Starting a business
14:05 - Working with competitors
19:14 - Truth behind funding
23:35 - Disrupting regulated industries
25:44 - Culture of risk evaluation
30:03 - Does the product change with scale?
34:08 - Looking for talent outside US
37:47 - Building out the culture of entrepreneurship
39:37 - The future of Alex in Rho

Why do we hire designers? Is it just to make things look pretty or can they actually drive revenue?

Well, according to Andy Budd, a proper design legend, one of the first UX designers in the United Kingdom and a VC nowadays, it's the latter.

We caught up with Andy during our recent visit to the How To Web conference in Bucharest, where we had the opportunity to pick Andy's brain on design and growth. He talked about the things that founders miss when it comes to design and about the things that designers miss and often overlook when it comes to actually running a profitable and scalable business.

As somebody who works on bringing those two sides closer through mentoring and consultancy work, our guest shared his views on product-led and founder-led marketing, noting that many founders are focused on product development and often overlook the significance of effective marketing and sales strategies:

"The founder’s involvement in sales and marketing is crucial for connecting with customers and building a successful growth strategy."

Throughout the episode, Andy took the time to explain why retaining users is a common challenge for startups, as founders often assume customers will instantly see the value of their product. He emphasized the need to prioritize usability and user onboarding, noting that customers usually need guidance to understand and utilize a product’s features fully. He stated:

"Founders should really resist the urge to continually add new features and instead focus on optimizing existing features to provide clear, accessible value."

Continuing our conversation, Andy underlined that UX plays an important role in a product’s success. Our guest encouraged founders to value design not just as an aesthetic element but as a strategic tool that can improve user engagement and business outcomes.

He also noted that design leaders should focus on measurable outcomes and collaborate with other departments to demonstrate the impact of design on the company’s growth and success — especially nowadays when organizations are trying to streamline their budgets.

Saving the best for last, Andy also gave us an insight into his latest book, The Growth Equation. This book summarizes the past 30 years of his work and discusses valuable principles for growing companies, teams, and revenue.

***

Engage with your customers over WhatsApp, SMS and iMessage – just like Uber, HubSpot and Meta → bit.ly/44xYxqy

***

Timestamps:

00:00 - Intro
01:49 - Falling in love with web design
03:38 - Discovering CSS
05:55 - Starting the first UX agency in UK
10:29 - Publishing "The Growth Equation"
13:37 - Founders on the frontlines
15:33 - It's not just about the product
20:47 - Usual mistakes about retention
25:40 - Understanding users
29:49 - What founders need to know about design
32:10 - Designing for profit
33:57 - Proving why design is valuable
37:09 - Design 2.0
39:56 - Being a team player

What is the role of marketing in a successful tech company? Do marketers only care about the brand, or are they more user-focused? In today’s episode, we talked with Andrew Davies, CMO of Paddle, a unicorn valued at over 1,4 billion dollars.

We explored the critical role of marketing in navigating the multiple ceilings that scale-ups face as they grow – particularly the importance of investing in a brand to avoid escalating customer acquisition costs.

Andrew opened up about the thoughts and fears that keep him up at night, particularly the challenge of understanding and reaching new customer segments as the Paddle continues to scale. He emphasized the need for continuous innovation and testing to uncover new areas of growth - especially when expanding beyond a tightly defined ideal customer profile.
 
Paddle’s CMO addressed the challenges of navigating market fluctuations and the importance of observation over prediction in understanding market dynamics. He also discussed the company’s approach to product-led, sales-led, and marketing-led growth strategies and the differences between these strategies.
 
Towards the end, Andrew touched on the importance of branding for tech companies, discussing how a strong brand can reduce customer acquisition costs and enhance demand generation. Our guest concluded with practical advice on fostering a brand that resonates with customers and drives long-term success.

***

Engage with your customers over WhatsApp, SMS and iMessage – just like Uber, HubSpot and Meta → bit.ly/44xYxqy

***

Timestamps:

00:00 - Intro
01:22 - What keeps you up at night?
03:41 - Testing is key
05:08 - Serving small businesses globally
07:09 - Recognizing the challenges in SaaS
09:44 - Signs of recovery
11:56 - Looking for markets outside US
13:36 - Marketing for scaleups
16:33 - How is Paddle helping other businesses?
18:14 - Growing with acquisitions
21:25 - Buying audiences for marketing purposes
23:00 - Different types of growth
27:51 - Product led growth
29:29 - Aligning the team
31:22 - Relationships with analysts
36:50 - Branding for scaleups
38:47 - Branding lessons from Paddle
42:52 - Actually investing in marketing
44:04 - Acquiring ProfitWell (the documentary)
46:36 - Content marketing done right
51:27 - AI impacts marketing talent
53:47 - Scaling skills and expertise

How does one go from a music journalist to a founder and CEO of one of the most recognizable companies in the web dev area?

This week, we talked with Mathias Biilmann Christensen, who, alongside his co-founder Christian Bach, started Netlify - a web builder / hosting company that supports more than 35 million websites globally.

Matthias shared his journey of building Netlify and the concept of Jamstack, which he coined to revolutionize web development by separating the user experience from backend logic. Throughout the episode, he explains how nurturing a community and investing in it pays off big time.

Our hosts IBB and Mia Biberovic explored the early days of Netlify, including the company's strategy of targeting key influencers in the developer community and the importance of a product-led approach. Mathias talked about Netlify's pricing model, which included a free plan that catered to open-source projects, helping to drive adoption.

Speaking of supporting the community, Biilmann explained how he and his team intentionally branded Jamstack to be inclusive and larger than just Netlify. He emphasized the significance of genuine community building and the pitfalls of trying to position oneself at the center of a new category.

We also touched on the cultural differences between the tech ecosystems in the United States and Europe, with our guest highlighting the unique optimism and risk-taking mentality found only in Silicon Valley. He shared personal anecdotes about his background as a music journalist and how his journey into tech was shaped by his passion for programming and problem-solving.

Finally, Matthias opened up about the human challenges faced in entrepreneurship, particularly during his co-founder’s battle with cancer, and the importance of maintaining a healthy perspective on identity and roles within a startup.

He concluded the talk by discussing the value of a distributed company culture and how music continues to play a significant role in his life, drawing parallels between music and programming - saying how composers were the first programmers!

Interested in the whole interview? Click the video below or find us on Apple Podcast, Spotify, or Pocket Casts!

***

Engage with your customers over WhatsApp, SMS and iMessage – just like Uber, HubSpot and Meta → bit.ly/44xYxqy

***

Timestamps:

00:00 - Intro
01:18 - What is Jamstack?
04:24 - Scaling Netlify
11:26 - Make scaling easier and more successful
17:38 - Early investors
20:54 - Why is Europe GOOD and BAD for startups?
26:16 - Setting up corporate and human values
37:25 - Personal story of Mathias Biilmann

What does it take to become one of the most prominent players in Web3 / blockchain community? How do you build tools for Web3 developers and how do you market them? How do you do all of this and become one of the fastest growing developer tooling companies?

This week, we talked to Bogdan Habic, co-founder and CTO of Tenderly, a full-stack infrastructure for Web3 professionals which was founded in 2018. and has so far raised almost 60 million dollars from VC’s such as Accel, Point Nine, Version One Ventures and Spark Capital. 

In this episode, Bogdan shared his experience with starting a Web3 company by coming from a Web2 community, highlighting the importance of understanding developer mindset and the need for reliable tools that they can use.

Our hosts, IBB and Mia Biberovic, explored how Tenderly transitioned from a tooling company to a broader infrastructure provider thanks to their investors and mentors. Habic emphasized the significance of community engagement and direct communication with users, which was pivotal in shaping their product offerings.

He also touched upon the subject of hiring in Web3 space, noting that most of their team comes from Web2 backgrounds and required training in order to adapt to the new enviroment. This nurturing approach became a cornerstone for their successful growth.

Throughout our conversation, Bogdan shared valuable lessons on navigating the complexities of developer marketing, the importance of building a strong company culture, and the need for continuous learning and adaptation in a rapidly evolving industry. Habic noted the parallels between the current AI boom and the Web3 landscape, suggesting that both fields are on the brink of mainstream acceptance.

Towards the end, our guest emphasized the importance of giving back to the community through initiatives such as Garaza which is aimed at supporting and mentoring the next generation of founders.

Timestamps:

00:00 - Intro
01:52 - How do you scale in Web3?
04:15 - Build it and they will come?
06:45 - Engineers as consumers
08:33 - Investor pep talk
10:52 - Market effect on Tenderly
12:52 - Web3 over promised the timeline not the value
15:24 - Hiring for Web3 space
18:57 - The NEW 20% RULE
23:49 - Community is everything
27:01 - Communicating with developers
28:32 - Giving back with Garaza

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Have you ever wondered what building and scaling products from the frontlines is like? To be at the intersection between customers and teams shaping digital tools and products?

This week, we discuss those questions with Hamid Palo, a former Director of Product at Trello and Uber with extensive knowledge and experience in product development. Our hosts, IBB and Mia Biberović, caught up with Hamid in Brooklyn, where this seasoned product leader talked about his career and experiences and shared valuable insights into the world of startups, scale-ups, and large organizations.

Hamid talked about his time at Trello, where he joined the company as employee number five. He recounted pivotal moments that led to Trello's acquisition by Atlassian, shedding light on the emotional rollercoaster and strategic decisions that followed. He reflected on the importance of people-first leadership and the challenges of letting go of ownership in a rapidly evolving organization.

Since our guest spent almost nine years at Trello and Atlassian, he also discussed people development in large organizations and how decision-making works from top to bottom.

After a short sabbatical in 2022, Hamid joined Uber, where he worked on grocery delivery, a new product at the time, bringing it to market from zero to one. He highlighted the significance of team ownership, accountability, and the iterative process of scaling a new product while emphasizing the value of storytelling and innovation.

As the conversation unfolded, Hamid shared his transition to working on his own AI company (like everybody these days!), showcasing his entrepreneurial spirit and commitment to tackling inefficiencies in the construction industry. Join us as we explore the intricacies of scaling products in the ever-evolving landscape of technology and business!

Timestamps:

00:00 - Intro
01:14 - In the beginning there was a developer
03:10 - Working on Trello for mobile
04:02 - Transition to product management
06:00 - Product management at Trello
09:06 - Localization vs. internationalization
10:59 - Trello's acquisition
13:35 - Atlassian did it the right way
14:30 - Culture is the key
15:28 - Atlassian's mistake
18:17 - Personal growth at Atlassian
21:05 - Taking time off
22:24 - Working on M&A
24:37 - High level decision making
26:38 - Putting out fires
30:09 - What makes a good leader?
32:35 - The importance of team ownership
34:13 - Boosting people's creativity
37:01 - Building new products at Uber
38:02 - How do you go Zero-to-One?
41:19 - Starting an AI company
43:33 - Pen and paper baby!

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What's the secret behind scaling not one, but two multi-million dollar companies?

What better person to talk to about growing businesses than Jason Cohen, the founder of WP Engine and someone who has been navigating the world of technology for more than 30 years!

In this episode, our hosts IBB and Mia talked with Jason about his passion for blogging and how it has been a key aspect of his journey as an entrepreneur. He emphasized the importance of writing to organize thoughts, share ideas, and receive feedback from the audience. Cohen highlighted the ego-driven aspect of blogging, where positive feedback and impact on readers serve as motivation.

Throughout the episode, our guest shared his experiences from bootstrapping to scaling using VC money - both with SmartBear and WP Engine. He talked about the critical shift in focus from exploration and experimentation to optimization and defense of existing strategies post-product market fit. He pointed out the challenges of managing rapid growth, including the need for effective delegation, as well as hiring the right people and adapting to changing organizational dynamics.

Cohen also touched upon the importance of hiring individuals who are not just skilled, but also passionate about their work. He shared his views on the need for hiring individuals who are better than the founders with the work they do, in order to drive further improvement and growth within the company.

Along with the hosts, our guest also discussed why founders choose to hire CEO's, why it's not an easy choice, and why the decision is always hard because of the ego. Stay with us for the rest of the interview as we explore the lessons behind scaling to hundreds of millions in revenue, and why starting a company is much about personal growth as well as it is about money!

Timestamps:

00:00 - Intro
01:20 - Blogging since 2007.
03:24 - Growing your audience
06:31 - Writing as a form of marketing
10:33 - This can help with the hiring
12:30 - Bootstrapping WP Engine
13:05 - Growing was a choice
15:30 - How to price your services?
16:51 - Why 2nd time founders fail?
17:13 - Bootstrapped vs. VS money growth
19:41 - Founders can be obstacles
22:06 - Hiring a CEO
26:35 - Solving bigger problems
32:04 - Why do OKR's fail?
32:36 - You can't use off the shelf solutions
34:05 - Should EM's be good at coding?
38:01 - Hire passionate people!
45:51 - Difference between juniors and seniors
48:11 - Navigating acquisitions
51:40 - Why is culture important?
54:49 - Why do founders leave?
56:32 - Ups and downs
58:54 - What is next for Jason Cohen?
01:02:06 - Life after scaleups

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Is there such a thing as overscaling the company? Is growth at all costs a good thing or can it actually harm the company and its culture?

Meet Wistia, a Cambridge-based video marketing platform for businesses which was founded in 2006. with a vision to create a competition website for filmmakers, and which later evolved into a fully customizable video solution for businesses with various editing and marketing tools at the user's disposal.

The story of Wistia is not the story of your average scaleup. Our hosts, IBB and Mia Biberovic, had the opportunity to talk to Wistia's CTO and co-founder, Brendan Schwartz, who shared the experiences of scaling rapidly and investing heavily in growth and the lessons behind the strategy that almost bankrupted the entire business.

Brendan gave us an insight into the decisions to go the standard VC route, why other paths were not as common a decade ago, as well as other challenges that he and his co-founder, Chris Savage, faced along the way. He talked about the importance of pivoting and how Wistia did it early on, and how working with experienced people affects the culture in the beginning when the team is still searching for product market fit.

One of the key moments for Wistia was when its co-founders started receiving offers to sell the company. After much deliberation, they decided not to do it but to instead raise $17,3 million in debt to buy out the investors and employees who had the equity. Schwartz also talked about shifting strategy from growth to profitability and how this move is especially important in 2024. when profitability is what everyone is talking about.

This episode of podcast puts special emphasis on open communication and transparency within the company, as well as the value of creative projects and long-term investments into content marketing. Join us as we share the unusual story of Wistia and share the business lessons that drive sustainable growth.

Timestamps:

00:00 - Intro
01:18 - From living room to first users
04:13 - Pivoting to video marketing tools
06:27 - Raising venture capital
08:51 - Hardest moments at growing the company
10:48 - CTO that loves the product
12:36 - Invest your profits back
15:21 - What went wrong with growth?
19:50 - Reaching the bottom
22:49 - Feeling depressed about work
24:18 - Should we sell the company?
27:38 - Deciding not to sell
30:34 - Buying out the investors
34:22 - Clear vision for the future
36:59 - Profitability over growth
39:46 - Investing back into content
42:33 - Running the business our own way
46:03 - Paying off the debt

Actually engage with your customers over WhatsApp, SMS and iMessage. Grow your startup or scaleup with Infobip’s platform – just as Uber, HubSpot and Meta! → bit.ly/44xYxqy

Boston-based office management tool Robin Powered faced a significant challenge at the beginning of 2020 when the world went into lockdown, making their business model obsolete overnight. Forced to adapt quickly, the company experienced its fastest-growing period by pivoting to meet the demands of the new work-from-home era.

During a visit to Boston, we interviewed Robin’s co-founder, Brian Muse, and current CEO, Micah Remley. They discussed the company’s evolution, the enduring relevance of hybrid work, and the mixed responses from companies regarding a return to the office. Brian shared the company's journey from an agency experimenting with various startups to creating a successful office management tool that helps companies manage workspaces and book desks and conference rooms.

With over 20 years of management experience, Micah talked about leading Robin through these changes and adapting to the shifting market landscape. He highlighted the need for companies to focus on revenue and sustainability, moving away from the era of raising large amounts of capital based on growth alone. 

Join us as we share the story of Robin Powered and the lessons behind running a scaleup in the ever-changing world of office space and the future of work!

Timestamps:

00:00 - Intro
01:16 - It all started with an agency
05:30 - Going all in
07:27 - Reaching Product Market Fit
09:02 - Why should we even exist anymore?
12:13 - Co-founders leaving
14:32 - Hiring a new CEO
17:04 - CEO's role in a Scaleup
20:26 - Biggest mistake founders make
21:40 - Onboarding a CEO
27:21 - What should CEO focus on?
30:16 - Being a CTO and a founder
32:27 - Impact of remote work on scaling Robin
34:11 - Downsides of remote work
36:30 - Working remote (States vs. World)
37:49 - Acquiring Flow n Form from Croatia
40:27 - Shifting to product mentality
44:26 - The impact of layoffs
47:10 - Art and science of running a scaleup
50:08 - Investing into relationships

Actually engage with your customers over WhatsApp, SMS and iMessage. Grow your startup or scaleup with Infobip’s platform – just as Uber, HubSpot and Meta! → https://bit.ly/44xYxqy