19 Entrepreneurs Share the Ups and Downs of Building Million-Dollar Startups

Building a startup is a challenging journey. One of the best ways to navigate this path is by learning from those who have walked it before you.

Imagine the excitement of raising millions in funding, the thrill of a successful exit, or the satisfaction of seeing your user base grow to tens of thousands.

In this comprehensive list, I’ve compiled all of the Startup Journey Interviews our team has conducted with successful entrepreneurs who have done just that.

These founders have faced numerous challenges, from pioneering fintech solutions to revolutionising customer communication, and have emerged with thriving startups.

Each story provides unique perspectives on how to build a startup, offering key takeaways that can help you turn your vision into reality.

Their experiences highlight the importance of resilience, innovation, and a strong team. Whether you’re just starting to build a startup or looking to scale your existing business, the lessons shared here will provide you with the knowledge and inspiration you need to succeed. Explore these interviews to discover actionable advice on product development, marketing, fundraising, team building, and much more.

1. Wade Eyerly — Multi-Exit Unicorn Founder

Wade Eyerly is a remarkable founder.

He started by pioneering subscription-based flying with his airline, which became a unicorn startup and recently completed a successful IPO. He then created an innovative fintech product to address a national student debt crisis.

His background also includes working as an economist at the Pentagon and serving a tour in Iraq.

Key Takeaways

• Innovative Thinking: Learn how Wade built an airline from scratch and revolutionised the industry with a subscription-based model.
• Risk-Taking and Career Shifts: Understand the bold moves Wade made, like leaving a stable, high-paying job to create a disruptive fintech product.
• Passion and Curiosity: Discover why Wade believes curiosity is his definitive superpower and how it fuels his entrepreneurial success.

Full interview: How This Unicorn Founder Built an Airline Out of Necessity

2. Diane Prince — Seven-Time Founder and Startup Advisor

Diane Prince is a seasoned entrepreneur with nearly three decades of experience in nurturing startups into successful businesses.

Having built seven companies that collectively generated over $300M in revenue and achieved five successful exits, Diane has left an indelible mark on the startup ecosystem.

As a business coach, she leverages her extensive experience to guide other founders on their journeys to build a startup.

This interview focuses on her first venture, Onstaff, highlighting timeless core tenets of entrepreneurship.

Key Takeaways

• Clarity in Goal Setting: Diane emphasises the importance of having clear objectives when you build a startup, whether it’s scaling, planning for an early exit, or seeking a strategic merger.
• Timeless Entrepreneurial Lessons: Learn from the foundational principles that have remained relevant from 1996 to today.
• Diverse Paths to Success: Understand the various paths Diane navigated in her career, providing insights for both aspiring entrepreneurs and seasoned business owners.

Full interview: 30-Year-Old Startup Lessons You Can’t Afford to Ignore

3. Bethany Stachenfeld — Sendspark

Bethany Stachenfeld, the co-founder and CEO of Sendspark, is revolutionising how companies connect with their customers through video communication.

In just three years, Bethany and her co-founders have raised over $1 million in funding and grown Sendspark to over 10,000 users.

In this interview, Bethany discusses her time at 500 Startups and how it helped her build a startup successfully.

Key Takeaways

• Insights into 500 Startups: Get a behind-the-scenes look at what it’s like to be part of 500 Startups and how it supports early-stage startups.
• Tips for Accelerator Applications: Learn valuable tips from Bethany on how to apply to startup accelerators and increase your chances of acceptance.
• General Startup Advice: Benefit from Bethany’s startup advice, including strategies that helped Sendspark achieve rapid growth and secure funding.

Full interview: How a Startup Accelerator Catapulted my Entrepreneurial Journey

4. Yaron Samid — BillGuard

Yaron Samid, a multi-exit startup founder, has seen his companies acquired by tech giants like Microsoft and Cisco.

He is also a regular lecturer at Stanford and Columbia business schools and the founder of TechAviv, one of the largest founder clubs in the world.

Yaron’s passion for helping the next generation of entrepreneurs is evident in his willingness to share his story of building and scaling the fintech startup BillGuard.

Key Takeaways

• Embrace Failure: Learn how Yaron’s early experience of getting fired for being “too creative” led him to the startup world, highlighting the importance of resilience and learning from setbacks.
• Innovative Thinking: Understand how Yaron’s innovative mindset helped him develop web-enabled solutions and eventually build successful tech companies.
• Building and Scaling: Gain insights into the strategies Yaron used to build and scale BillGuard, making it one of the most popular fintech startups globally.

Full interview: From Being Fired to Building a Multi-Million Dollar Fintech Startup

5. Matt Willamson — Vizzly

Matt Williamson, a first-time founder with an extensive background in business development and product from his time at Skyscanner and Duffel.

He founded Vizzly to make data accessible and digestible through customer-facing dashboards.

Targeting B2B SaaS apps and marketplaces and prioritising data transparency with external stakeholders, Vizzly emerged from a market gap ripe for a solution.

Key Takeaways:

• Importance of Data Accessibility: How Vizzly simplifies the journey from raw data to actionable insights through intuitive dashboards.
• Market Opportunity Identification: Leveraging Matt’s industry experience to identify and fill a crucial market gap.
• Y Combinator’s Influence: The role of Y Combinator in providing mentorship, resources, and credibility to accelerate Vizzly’s growth.

Full interview: Navigating Rapid Startup Growth: From Bootstrapping to Y Combinator

6. Garrett Gafke — Serial Entrepreneur & Silicon Valley Veteran

Garrett Gafke, a seasoned serial entrepreneur, pioneered the digital identity industry with his startup IdentityMind, founded in 2011.

After securing over $21M in funding and establishing IdentityMind as an industry leader, it was successfully acquired by Acuant.

Garrett’s journey is a testament to the challenges and triumphs that come with building a startup.

Key Takeaways

• Mindset and Resilience: Learn about the critical importance of having the right mindset, grit, and resilience in the face of countless rejections and market challenges.
• Scrappiness and Resourcefulness: Discover how being scrappy and resourceful can help you and your team push through difficult times and build a startup successfully.
• Founding Team Commitment: Understand the value of commitment to your co-founders and how these relationships can sustain you through tough times.

Full interview: How a Lot of Rejection Turned into $21M in Funding

Continuing the conversation, Garrett Gafke shared more insights into building a startup, focusing on onboarding early adopters, leadership, maintaining a positive company culture, and the key lessons from his extensive experience in Silicon Valley.

This part delves deeper into the operational and human aspects of startup success.

Key Takeaways

• Onboarding Early Adopters: Strategies for attracting and retaining early users who are crucial for product validation and growth.
• Leadership and Team Dynamics: Insights into effective leadership and the importance of building a strong, cohesive team.
• Positive Company Culture: Tips on fostering a positive and productive company culture that can drive your startup forward.
• Lessons Learned: Key takeaways from Garrett’s extensive experience that can benefit any founder starting their entrepreneurial journey.

Full interview: Lessons Learned From Over 25 Years in Silicon Valley

7. Adarsh Jain — ThirdWatch

Adarsh Jain, a technical founder with over 12 years of experience as a CTO and entrepreneur, co-founded Thirdwatch to combat e-commerce fraud using AI, machine learning, and data sciences.

His startup was the first acquisition of RazorPay, a rapidly growing fintech valued at $7.5B.

Adarsh’s journey is a testament to the power of technical expertise in building a startup that addresses real-world problems.

Key Takeaways

• Identifying Real-World Problems: Learn how Adarsh identified a significant problem in e-commerce fraud and developed a technological solution to address it.
• Leveraging Technical Expertise: Understand the importance of technical knowledge and how it can be leveraged to create innovative solutions in the startup ecosystem.
• Successful Acquisition: Gain insights into how Thirdwatch’s expertise in AI and machine learning led to its acquisition by RazorPay and how it continues to impact the e-commerce industry.

Full interview: From Struggling to Buy a TV to Getting Acquired by a $7.5B Fintech

8. Giacomo De Lorenzo — Moneymour

Giacomo De Lorenzo, the co-founder of fintech startup Moneymour, leveraged his network to build a strong foundation for his business.

His approach to gathering valuable feedback and advice from early connections led to a robust project that attracted the interest of fintech unicorn Klarna even before its launch.

Giacomo’s journey underscores the importance of people and relationships in building a startup.

Key Takeaways

• Value of Relationships: Learn how Giacomo’s connections provided critical advice and feedback during the early stages of Moneymour, highlighting the importance of leveraging your network.
• Foundations of a Fintech Startup: Discover the steps Giacomo took to build a solid foundation for his Fintech product, making it attractive to major players like Klarna.
• Early Engagement and Feedback: Understand the benefits of seeking input from advisors, investors, and clients early in the startup process to refine and strengthen your offering.

Full interview: Selling a Fintech by Leveraging Your Most Valuable Resource: People

9. Alex Tonelli — Fintech Founder and Serial Entrepreneur

Back in 2009, Alex faced the daunting challenge of securing a small business loan for his chain of fitness centres, despite having six profitable units.

The bureaucratic hurdles and endless paperwork led him to solve this problem for other small businesses. Today, his solution is a unicorn fintech startup making small business financing easy and affordable.

In addition to his success in fintech, Alex is a Partner at Endurance Companies, leading a Venture Lab focused on building mission-driven companies in healthcare and fintech.

During our conversation, he shared lessons learned as a young founder and offered actionable tips on product development, funding, and hiring.

Key Takeaways

• Overcoming Financing Hurdles: Learn how Alex transformed his struggle with securing business loans into a successful fintech solution that simplifies financing for small businesses.
• Product, Funding, and Hiring Tips: Gain actionable insights on developing your product, securing funding, and building a strong team from Alex’s experiences.
• Mission-Driven Entrepreneurship: Understand the importance of mission-driven goals in building sustainable and impactful companies, particularly in healthcare and fintech.

Full interview: Lessons Learned from the Early Days of a Fintech Unicorn

10. Peter Fishman — Mozart Data

With nearly two decades of tech experience, Peter Fishman’s impressive portfolio includes stints at Google, The Walt Disney Company, and a key role as Principal Data Science Manager at Microsoft.

Three years ago, he set out to build Mozart Data, an innovative startup that democratises the complex process of data management.

Mozart Data allows mid-stage startups to access high-quality data platforms previously available only to large corporations.

Key Takeaways

• Challenges of Building a Startup: Learn about the initial challenges Peter faced while building Mozart Data and how he overcame them.
• Insights from Y Combinator: Discover valuable insights from Peter’s experience at Y Combinator, including the importance of talking to customers and doing things that don’t scale.
• Customer-Centric Philosophy: Understand how a customer-centric approach has been instrumental in shaping Mozart Data’s identity and driving its success, emphasising the value of working for customers, often for free, to build future relationships.

Full interview: How a Y Combinator Lesson Helped Our Startup Scale to $19M

11. Jan-Philipp Kruip — FitSense

Jan-Philipp Kruip is the founder of FitSense, a B2B health and fitness fintech startup used by some of the largest multinational insurance companies in the world.

In this conversation, Jan-Philipp shared how trusting his gut led to some of his biggest wins.

He also provided valuable insights on critical elements of building a startup.

Key Takeaways

• Trusting Your Gut: Learn how Jan-Philipp balanced empirical data with intuition to achieve significant successes in his entrepreneurial journey.
• Product Development: Gain insights into creating a compelling product that meets market needs and stands out in the fintech industry.
• Effective Marketing: Understand strategies for marketing your startup effectively to attract and retain customers.
• Building a Strong Team: Discover tips on hiring the right talent to drive your startup forward.
• Raising Capital: Learn best practices for securing funding and managing investor relationships.

Full interview: Building and Scaling a Fintech Startup by Trusting Your Gut

12. Christian Nothacker — PrestaCap

Christian Nothacker, founder of fintech startup PrestaCap, identified a significant market gap while working at mobile payments company SumUp.

Small business owners faced major inefficiencies in traditional bank financing processes. Seeing an opportunity, Christian built a team to digitalise these processes, creating PrestaCap.

Although the initial business model required adjustment, Christian’s strategic decisions led to PrestaCap being acquired by DEPObank, one of Italy’s largest private-equity-backed banks, for over $20M just five years later.

Key Takeaways

• Identifying Market Gaps: Learn how Christian spotted inefficiencies in the traditional banking system and seized the opportunity to create a fintech solution.
• Aligning Value Proposition and Business Model: Understand the importance of aligning your value proposition with a sustainable business model, and how Christian navigated this process.
• Successful Acquisition: Gain insights into the strategic decisions that led to PrestaCap’s successful acquisition and what it takes to build and scale a fintech startup.

Full interview: The Key Decisions When Building a Fintech

13. Bilal Dahlab — Moneco

Bilal Dahlab transitioned from financial consulting to launching Moneco, a fintech startup that simplifies setting up bank accounts and making international money transfers for the African diaspora living in Europe.

His journey through Y Combinator provided him with invaluable resources, mentorship, and a powerful network, significantly enhancing his startup experience.

Key Takeaways

• The Decision to Join an Accelerator: Learn why Bilal chose to join Y Combinator and how this decision impacted his startup journey.
• Access to Resources and Mentorship: Discover the benefits of tapping into Y Combinator’s resources and the mentorship opportunities that come with being part of an accelerator.
• Building a Supportive Network: Understand the importance of the community Bilal became a part of and how it has supported his entrepreneurial efforts.
• Advice for Aspiring Entrepreneurs: Gain practical advice from Bilal for those considering the accelerator route, highlighting the real-world benefits and challenges of participating in Y Combinator.

Full interview: Raising $3.3M Pre-Launch Bridging Europe & Africa’s Financial Chasm

14. Ali Halabi — Volt Lines

Ali Halabi moved to Istanbul in 2013 and quickly fell in love with the city but was frustrated by the daily traffic.

Determined to solve this problem, he left his corporate job and founded an on-demand carpooling service called Volt in 2014. However, Volt struggled to achieve product-market fit and eventually failed.

Ali’s commitment to solving the traffic problem led him to pivot. He shifted focus to a B2B subscription-based travel solution for corporate users, rebranding as Volt Lines.

Since its launch in 2017, Volt Lines has raised over $7.5M in funding.

Key Takeaways

• Fall in Love with the Problem: Understand the importance of focusing on the problem rather than a specific solution, as demonstrated by Ali’s journey.
• Dealing with Failure and Pivoting: Learn how Ali navigated the failure of Volt and successfully pivoted to create Volt Lines, a solution that resonated with the market.
• Actionable Entrepreneurial Advice: Gain insights from Ali’s experiences, including dealing with mistakes and what he would do differently in hindsight.

Full interview: How to Build a Million Dollar Startup by Falling in Love With a Problem

15. Illit Geller — TradAir

Illit Geller, a serial entrepreneur, founded TradAir, a fintech startup that recently raised $11M in its latest funding round.

Illit’s approach to building a startup involved close collaboration with her target market, developing solutions directly with their input. Her focus on team dynamics and leadership has been a key factor in TradAir’s success.

Key Takeaways

• Market-Driven Product Development: Learn how Illit developed TradAir’s product in partnership with a bank, ensuring the MVP was perfectly aligned with market needs.
• Team Focus: Discover the importance of focusing on your team as a CEO, ensuring everyone understands the bigger picture and is supported in their roles.
• Leadership Insights: Understand the value of taking care of your staff, as emphasised by Sir Richard Branson’s famous quote, and how this philosophy leads to better customer care and overall success.

Full interview: Building a Successful Fintech by Listening to the Market

16. Gary Lin — Airwork

Gary Lin, a seasoned software engineer with experience at tech giants like Facebook and NVIDIA, built Airwork, a platform that allows workers in Canada to pick up shifts at local businesses and get paid the same day.

Accepted into the Winter 2022 batch of Y Combinator, Gary’s startup has rapidly grown, raising over $1.5M and revolutionising accessibility to shift work in the Greater Toronto area.

Key Takeaways

• Pivoting for Success: Learn how Gary’s initial startup idea, Litebulb, pivoted from a B2B SaaS platform for tech interviews to Airwork, focusing on the gig economy.
• Experiences at Y Combinator: Gain insights into the valuable lessons and experiences Gary acquired during his time at Y Combinator.
• Building a Resilient Startup: Understand the challenges and strategies involved in successfully launching and scaling a startup, including the importance of adaptability and market fit.

Full interview: How Y Combinator Taught Me What Matters When Building a Startup

17. Sean Yu — Paraşüt

Sean Yu began his career at Lehman Brothers and Gryphon Investors, with a rational path leading him towards business school and a stable finance career.

However, his interest in economic development led him to work with an NGO in Turkey, where he discovered his entrepreneurial passion.

Inspired by the local entrepreneurs, Sean decided to stay and launch Paraşüt, a startup that has since been acquired by Turkey’s largest private equity firm.

Sean continues to lead Paraşüt as CEO, managing a team of over a hundred people.

Key Takeaways

• Following Your Passion: Learn how Sean transitioned from a stable finance career to entrepreneurship, driven by his desire to build and create.
• Startup to Acquisition: Gain insights into the journey of building Paraşüt from the ground up and achieving a successful acquisition.
• Maintaining Startup Culture: Understand the challenges and strategies Sean employs to maintain the qualities of a startup within a larger company structure.

Full interview: How an Experience in Turkey Led to a Million-Dollar Startup

18. Reed Taussig — Outseer

Reed Taussig, an entrepreneur, business leader, and VC with over 35 years of experience, has led, advised, and invested in numerous tech corporations and startups.

He notably managed Callidus Cloud from inception to IPO, spearheaded ThreatMatrix from pre-product launch to acquisition by Lexis Nexis Risk Solutions, and currently serves as CEO of Outseer.

Reed was brought in to transform Outseer from a traditional corporate environment into a lean startup.

Key Takeaways

• Adopting Startup Culture: Learn how Reed successfully integrated startup culture into Outseer, moving away from traditional corporate structures.
• Leadership through Change: Discover the challenges and strategies involved in managing cultural transformation and the impact on staff retention.
• Effective Transformation Tactics: Gain insights into the core values and processes Reed implemented to revolutionise Outseer’s operations, creating a more agile and innovative company.

Full interview: Applying the Startup Mindset to Big Corp & Losing Half Your Your Staff

19. Ankit Singh — MyPoolin

Ankit Singh, a Forbes 30 under 30 founder, has extensive experience in the financial technologies landscape.

In 2015, he founded MyPoolin, a peer-to-peer payment platform that disrupted the Indian fintech market.

Less than four years later, MyPoolin was acquired by California-based fintech startup Wibmo, where Ankit continued as Director of Business and Product for an additional three years.

Key Takeaways

• Disrupting the Fintech Market: Learn how Ankit’s innovative approach with MyPoolin disrupted the Indian fintech market and set the stage for success.
• Path to Acquisition: Understand the journey from startup to acquisition and the strategies Ankit employed to make MyPoolin attractive to Wibmo.
• Building a Fintech Startup: Gain valuable tips from Ankit on how to build a successful fintech startup, drawing from his years of experience and insights in the industry.

Full interview: Starting And Selling a Fintech Startup in Less Than 4 Years

Wrapping Up

The insights shared by these successful entrepreneurs provide invaluable guidance on how to build a startup.

From navigating the complexities of funding and pivoting business models to leveraging accelerator programs and fostering strong team dynamics, each story offers unique lessons.

The key takeaways emphasise the importance of resilience, innovation, and a customer-centric approach.

By learning from these experiences, you can better prepare yourself to build a startup that not only survives but thrives in today’s competitive landscape.

I hope by exploring these interviews, you’ve come away with a slew of practical advice to help you turn your vision into reality.

If you’re looking for more advice directly related to your startup journey, reach out directly. I’d be happy to put you in touch with the right person from our team to help.