Join Matt Watson and Steve Satoru Naito, Co-founder and CEO of Anyplace, as they explore his journey from immigrant to Series B and the creation of digital nomad accommodations. Steve and Matt share insights into the unique challenges faced as first-time entrepreneurs. They delve into the shifting focuses between Series A and B and the intricate dynamics of supply and demand in the short-term rental market.
 
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This episode is sponsored by Full Scale:
https://fullscale.io
 
Learn more about Anyplace:
https://www.anyplace.com
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From Immigrant to Series B and Creating Digital Nomad Accommodations

Startup Hustle is a podcast for entrepreneurs, by entrepreneurs.&nbsp; With the mission of telling the real story of startups and entrepreneurs, topics range from funding to failure and beyond.&nbsp; If you want to start, own, or build a business then you're in the right place.&nbsp; &nbsp;

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In this compelling episode, join Matt Watson as he sits down with Stefan Schmidt, a seasoned CTO coach and author of the acclaimed book "Amazing CTO." Together, they discuss the pivotal role of a Chief Technology Officer (CTO), exploring crucial insights on when to bring one on board and the critical errors to avoid in the selection process.
Stefan underscores the importance of idea validation before engaging a CTO or developer and suggests starting with a PowerPoint slide deck to gather feedback. Moreover, he advocates for aligning with a co-founder who not only shares the product vision but also has industry expertise.
As the conversation unfolds, Stefan navigates the intricacies of company expansion, underscoring the pivotal role of delegating tasks and strategically appointing team leaders. He underscores the critical need for CTOs to shift towards strategic direction, avoiding the trap of being consumed by routine coding tasks.
Leveraging his wealth of experience, Stefan's book serves as a treasure trove of wisdom, providing CTOs with 140 actionable rules meticulously tailored to their needs. From mastering delegation techniques to nurturing employee growth and circumventing common challenges, his insights offer indispensable guidance for navigating the ever-evolving realm of technology leadership.
 
Takeaways

Validate your idea before hiring a CTO or developer
Find a co-founder who shares the product vision and has experience in the industry
Delegate tasks and hire team leads as the company grows
Focus on strategy and vision as a CTO, rather than getting caught up in day-to-day coding

 
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
 
This episode is sponsored by Full Scale:
https://fullscale.io
 
Visit the Amazing CTO website: 
https://www.amazingcto.com
 
Learn more about Stephan Schmidt:
https://www.linkedin.com/in/stephanjschmidt
 
Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz 
 
Highlighted Discussion Points

Validating startup ideas before hiring developers. 0:51
Finding a technical co-founder for a startup. 5:22
Hiring a CTO for early-stage startups, with insights on product vision, ownership, and team leadership. 10:13
Challenges faced by CTOs in scaling their teams, including delegation, team leads, and maintaining technical expertise. 17:30
CTOs prototyping and delegating tasks to bring joy to the job. 26:37
CTO coaching, delegation, and leadership challenges. 30:47

  See omnystudio.com/listener for privacy information.

The Evolving Role of the CTO

In this episode of Startup Hustle, Matt Watson interviews Robby Yates, co-founder and Chief Everything Officer of FollowApp, a networking software company. They discuss Robbie's journey from being a salesperson to becoming an IT guy and starting his own company. They also talk about the importance of networking, the challenges of being a non-technical founder, and the benefits of white labeling. Robby shares tips for effective networking and emphasizes building a strong team and listening to others. He also highlights the importance of perseverance and believing in oneself as an entrepreneur.
Important Takeaways

Networking is a valuable tool for entrepreneurs and should be approached with intention and a focus on helping others.
Building a strong team and listening to advisors are crucial for success as a non-technical founder.
White labeling can be a game changer for a business, allowing for easier promotion and increased revenue.
Effective networking requires being yourself, not wearing a mask, and following up with contacts.
Raising funds can be challenging, but networking events can lead to unexpected opportunities.
It's important to embrace rejection and keep going, believing in oneself and the value of the product or service being offered.

Don't miss this insightful conversation about becoming a non-tech founder in the tech world. 
 
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
 
This episode is sponsored by Full Scale:
https://fullscale.io
 
Visit the Follow App website: 
https://thefollowapp.co 
 
Learn more about Robby Yates:
https://www.linkedin.com/in/robert-yates-130105 
 
Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz
 
Highlighted Discussion Points

Creating a software company, challenges and lessons learned. 0:31
Entrepreneurship, trust, and business growth. 6:03
Pricing sensitivity and value-based pricing, with a focus on B2B vs. B2C. 10:53
White labeling software, networking, and app deployment. 12:43
Networking strategies for introverts and extroverts. 17:49
Using software to manage networking at events. 22:33
Entrepreneurship, networking, and fundraising challenges. 25:41
Building a tech company, overcoming challenges, and staying motivated. 30:44

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From Sales Guy to Tech Founder

Join us as Chase Harmer, a seasoned entrepreneur with over 20 years in the fintech industry, dives deep into the challenges and innovations of building a fintech company with heart. In this episode, we explore the intersection of financial technology and charitable giving through Chase's latest venture, Wishes—a platform designed to transform how we support causes we care about.
Episode Highlights:

The Genesis of Wishes: From overcoming compliance hurdles to raising $30 million, Chase shares the behind-the-scenes of starting and scaling a fintech venture focused on solving real-world problems, such as hotel booking issues and incentivizing charitable donations with cashback rewards.
A New Era for Charities: Discover how Wishes is redefining charitable giving by ensuring transparency, reducing administrative costs, and enhancing donor engagement through innovative features like virtual cards and a rewards system.
Blockchain Meets Charity: Learn about the role of blockchain in fintech and how Wishes utilizes this technology alongside traditional systems to create a hybrid model that promotes transparency and efficiency in charitable transactions.
The Cost of Innovation: Chase breaks down the financial realities of building a fintech company—from the initial $2 million launch cost to ongoing platform and compliance expenses.
Strategic Nonprofit Partnerships: Hear how Wishes is not just a tech platform but a community builder, fostering strong connections between nonprofits and donors, and addressing challenges like homelessness through financial technology.
Looking Ahead: Chase discusses the future of fintech in the nonprofit sector and his vision for scaling Wishes to ensure a positive impact on the charity landscape.

Don't miss this insightful conversation about the fusion of technology and philanthropy, where passion meets purpose in the fintech space.
 
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
 
This episode is sponsored by Full Scale:
https://fullscale.io
 
Visit the Wishes Inc. website: 
https://www.wishes.inc
 
Learn more about Chase Harmer:
https://www.linkedin.com/in/chase-harmer-657a5b5
 
Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz
 
Highlighted Discussion Points

Entrepreneurship, FinTech, and building a charity-related FinTech company. 0:32
Building a tech company in FinTech, compliance challenges, and scaling. 3:42
Charity platform Wishbone, its features, and how it solves problems in the charity space. 9:48
Charity work and nonprofit alignment in FinTech industry. 15:31
Blockchain technology and its potential in the financial industry, with a focus on transparency and revenue generation for non-profit organizations. 18:07
The high costs of building and maintaining a FinTech company, including compliance, platform fees, and ongoing expenses. 23:45
Startup challenges and nonprofit fundraising strategies. 29:08
Nonprofit fundraising and payment processing. 31:38
Disrupting the nonprofit charitable giving industry with innovative technology. 37:01
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Navigating FinTech Challenges and Charitable Giving Tech Solutions

Steve Wolfe, managing partner and co-founder of Growth Street Partners, joins Matt Watson on the Startup Hustle podcast to discuss practical fundraising for founders. They explore the challenges faced by practical founders in raising money and the drawbacks of traditional venture capital funding. They emphasize the importance of founder market fit and the advantages it brings. They also discuss the benefits of having a growth equity firm like Growth Street Partners as an investor, including the ability to provide liquidity to founders and the flexibility to scale at a pace that suits the business.
The episode reveals the following insights:

Founder market fit is crucial for success. Entrepreneurs with experience, expertise, and passion for solving the problems their business addresses have a competitive advantage.
Traditional venture capital funding may not be suitable for practical founders. It often requires raising large amounts of money and focuses on rapid growth, which may not align with the goals and needs of practical founders.
Growth equity firms like Growth Street Partners provide an alternative for practical founders. They invest in companies that have proven their product but need capital to scale. They offer a unique solution for practical founders serving medium-sized addressable markets.
Having the right team, industry connections, funding and resources, a first-mover advantage, an existing customer base, and a world-class team can all contribute to a founder's success.
Growth Street Partners helps practical founders navigate scaling challenges, providing guidance on hiring, sales and marketing, and strategic decision-making.

So, jump in and learn about practical funding and founder-market fit!
 
 
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
 
This episode is sponsored by Full Scale:
https://fullscale.io/
 
Visit the Growth Street Partners website: 
https://growthstreetpartners.com 
 
Learn more about Steve Wolfe:
https://www.linkedin.com/in/stephen-wolfe-ba5a596/ 
 
Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz/ 
 
Highlighted Discussion Points

Raising money for startups with a focus on practical founders and scalability. 0:31
Venture capital funding and growth strategies for startups. 4:25
Investing in startups, prioritizing financial stability. 11:30
Potential downsides of venture capital funding include loss of decision-making control and unrealistic expectations. 16:12
Startup funding, founder market fit, and the risks involved. 20:36
Investment philosophy, industry connections, and funding resources. 24:57
Key factors for startup success include team, capital, and existing customers. 29:22
Scaling challenges for B2B SaaS companies, with product, sales, and marketing insights. 36:00
See omnystudio.com/listener for privacy information.

Practical Funding & Founder-Market Fit

In this episode, Matt Watson interviews Rob Snyder, the founder and CEO of Reframe, about product market fit and the challenges of being an entrepreneur. They discuss the definition of product market fit, the importance of customer case studies, and the need to focus on solving specific problems for a target audience.
Rob shares insights from his program for founders and emphasizes the value of talking to customers and iterating on the sales pitch. They also touch on the difficulty of scaling and the limitations of traditional business education in teaching early-stage startup strategies.
The conversation explores the challenges of finding product-market fit and starting a business. It emphasizes the importance of focusing on customer needs and simplifying the process of building a startup. Matt and Rob discuss the common struggles of not knowing how to build the right product or sell it effectively. They highlight the need to listen to customers' problems rather than their proposed solutions and to frame everything in the context of a customer success story. The conversation also touches on the value of a Harvard degree in entrepreneurship and the ongoing desire to start new ventures.
Tune in to learn that product market fit is not all that complicated.
 
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
 
This episode is sponsored by Full Scale:
https://fullscale.io
 
Visit the Reframe website:
https://www.robsnyder.org
 
Learn more about Rob Snyder:
https://www.linkedin.com/in/rsnyder1
 
Highlighted Discussion Points

Product market fit, with a focus on repeatable customer success stories. 0:31
Helping startups find product-market fit through customer understanding and messaging. 3:47
Finding and serving early customers for startups. 9:18
Product market fit and scaling a business. 16:21
Product development and customer feedback. 22:02
Product development and customer success. 28:14
Product market fit and pivoting in startups. 31:22
Product development and scaling startups. 37:08

  See omnystudio.com/listener for privacy information.

From Immigrant to Series B and Creating Digital Nomad Accommodations

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