Startup Hustle

In this episode, Matt Watson speaks with Joseph Ruscio, a partner at Heavybit, a venture capital firm focused on investing in software development-related companies. They discuss the evolving landscape of venture capital, the unique value niche VC firms provide, and the impact of AI on software development. Joseph shares insights on the challenges developers face, the importance of finding product-market fit, and how AI can enhance developer productivity. They also explore Heavybit's recent investments in AI startups and the future of software development in an AI-driven world.

Takeaways
AI is not going to replace developers but will enhance their capabilities.
Niche VC firms like Heavybit provide specialized support to early-stage companies.
The pressure to integrate AI into products is significant for developers.
Finding product-market fit is crucial for startup success.
Developers are increasingly seen as the key decision-makers in technology.
The cost of software development varies widely across different markets.
AI tools can help reduce the toil in software development processes.
Investing in specialized AI models is essential for enterprise applications.
The landscape of AI investments is rapidly evolving with new startups emerging.
Understanding the unique challenges of selling to developers is vital for success.

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This episode is sponsored by Full Scale:
https://fullscale.io/

Find out more about Heavybit here:
https://www.heavybit.com

Learn more about Joseph Ruscio here:
https://www.linkedin.com/in/josephruscio/

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https://newsletter.startuphustle.xyz/

Sound Bites
"AI is going to make developers more valuable."
"The pressure to build AI functionality is real."
"Finding product market fit is crucial."

Chapters
00:00 Introduction to Heavybit and AI in Software Development
03:01 The Evolution of Venture Capital and Specialization
05:58 The Value of Niche VC Firms
09:01 Challenges in Selling to Developers
11:48 AI's Impact on Software Development
14:46 Investments in AI Companies
17:51 The Future of Software Development with AI
20:54 The Role of AI in Developer Productivity
23:53 Investing in Emerging AI Startups
27:08 The Importance of Specialized AI Models
30:12 The Landscape of AI Investments
33:06 The Economics of Software Development
35:54 Conclusion and Future Outlook

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In this episode, Matt Watson and Yoni Kozminski discuss the intricacies of hiring talent in the Philippines, exploring Yoni's journey from creative advertising to building a recruitment agency. They delve into the challenges of scaling a business, the importance of value creation in sales, and the need for clear job definitions and onboarding processes. 

The conversation highlights the evolving workforce in the Philippines, cultural nuances in communication, and the economic factors influencing hiring decisions. Yoni emphasizes the importance of having in-house expertise and leadership when hiring remote talent, while also acknowledging the incredible capabilities of Filipino workers.

Takeaways
Hiring in the Philippines can provide high-quality talent at competitive rates.
Value creation is essential in every interaction with potential clients.
Understanding business needs is crucial before defining job roles.
A clear onboarding process is key to employee success.
Cultural nuances can affect communication and understanding in remote teams.
The Philippines has a rapidly evolving workforce with increasing capabilities.
Investing in emerging world talent is beneficial for both parties.
Sales growth often comes from existing clients and referrals.
Defining success metrics for roles helps in effective hiring.
Building a strong company culture can enhance employee satisfaction.

Find Startup Hustle Everywhere:
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This episode is sponsored by Full Scale:
https://fullscale.io/

Find out more about MultiplyMii here:
http://www.multiplymii.com

Learn more about Yoni Kozminski:
https://www.linkedin.com/in/yonkoz/

Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz/

Sound Bites
"We could help a lot of people if they just understood."
"You really have to have visibility across how each of the pieces connect."
"How do we focus on adding value at every single stage?"

Chapters
00:00 Introduction to Hiring in the Philippines
02:59 Yoni's Journey into Recruitment
06:04 Scaling the Business: Challenges and Strategies
09:13 Sales Growth and Value Creation
12:03 Understanding Roles and Hiring Needs
15:04 Defining Success in Hiring
17:58 The Importance of Onboarding
20:49 Expertise and Leadership in Hiring
24:02 The Evolving Workforce in the Philippines
26:58 Opportunities and Economic Factors
30:08 Cultural Nuances in Communication
32:57 Conclusion and Final Thoughts

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In this episode, Matt Watson interviews Andrew Plato, a seasoned entrepreneur and author of 'The Founder's User Manual.' They discuss the challenges of entrepreneurship, the importance of differentiation in a competitive market, and the role of trust and credibility in business. Andrew shares insights from his experiences, emphasizing the need for startups to establish a unique identity, navigate employee relationships carefully, and maintain a clear company culture. He also addresses the importance of avoiding controversial topics at work and the necessity of perseverance in the face of challenges.

Takeaways
Writing the book was a therapeutic process for Andrew.
Books can provide valuable insights but cannot replace real experience.
Startups must differentiate themselves to stand out in a crowded market.
Building trust is essential for successful business relationships.
Establishing boundaries with employees is crucial for effective leadership.
Company culture should prioritize safety and open communication.
Avoiding controversial topics at work can prevent division.
Choosing the right customers is vital for business integrity.
Perseverance is key to overcoming challenges in entrepreneurship.
Successful entrepreneurs refuse to give up and take ownership of their choices.

Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5

This episode is sponsored by Full Scale:
https://fullscale.io/

Find out more about Zenaciti here:
https://zenaciti.com

Check out Andrew Plato's book Founder's User Manual here:https://zenaciti.com/founders-user-manual/

Learn more about Andrew Plato:
https://www.linkedin.com/in/andrewplato/

Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz/

Sound Bites
"You can't go into a marketplace and say you're unique and special and different if you do what everybody else does or you sound like everybody else."
"Less is more. I get emails all the time and I get marketing all the time and it's like a wall of text. I don't care. I don't care that you have this guy on your board. I don't care that you know so-and-so. I don't care that you worked at Microsoft back in the 90s."
"You need to go out into the marketplace and speak about the things that are interesting to people. Don't talk about your product. Don't talk about your competitors. Talk about things that are relevant in your field."
"I wanted to be a likable person."
"The harder I tried to be everybody's friends kind of, the more it ultimately backfired on me."
"If you allow your business to become dominated by any or either of those sides, you are excluding a huge chunk of the population."

Chapters
00:00 Introduction and Background of Andrew Plato
04:02 The Challenges and Learning Curve of Entrepreneurship
07:57 Standing Out in a Crowded Marketplace
11:56 The Power of Clear Messaging and Niching Down
14:49 Building Trust and Credibility
18:15 Building Mutually Beneficial Partnerships
20:28 The Challenges of Being a Leader
28:40 Setting Boundaries and Creating a Safe Space
30:33 The Impact of Discussing Controversial Topics
34:40 Focusing on Customer Needs and Avoiding Judgment
40:50 The Power of Perseverance

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Adam Robinson, founder and CEO of Retention, discusses his new product RB2B and the importance of simplicity and profitability in building a successful business. He emphasizes the value of bootstrapping and achieving $10 million ARR before considering raising funds. Adam challenges the traditional venture-backed model and highlights the benefits of owning a profitable business that generates millions of dollars in revenue. He also shares his experience with scaling companies efficiently and the dangers of over-hiring and overspending. 

The conversation explores the challenges of outbound marketing and the importance of creating a disruptive offer to drive growth. It emphasizes the value of using satisfied customers to fund business growth through referrals and expansions. The concept of inbound-led outbound marketing is introduced, highlighting the need for strong, intense signals to capture attention. The conversation also delves into the power of thought leadership and organic social media content in driving demand. The discussion concludes with a focus on the benefits of engaging in public battles and the importance of building a personal brand and thought leadership to create a following and generate referrals.

Takeaways
Bootstrapping to $10 million ARR before considering raising funds can lead to a more profitable and sustainable business.
Simplicity and ease of use are key factors in building a scalable product.
Many SaaS companies struggle to achieve profitability due to over-hiring and overspending.
Focusing on long-term profitability and cash flow can be more rewarding than pursuing a quick exit.
The traditional venture-backed model may not be the best fit for all businesses, and alternative paths to success should be considered. Outbound marketing has become more challenging, making it important to create a disruptive offer to stand out.
Using satisfied customers to fund business growth through referrals and expansions is a sound way to run a business.
Inbound-led outbound marketing requires strong, intense signals to capture attention.
Thought leadership and organic social media content are powerful tools for driving demand.
Engaging in public battles, building a personal brand, and thought leadership can create a following and generate referrals.

Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5

This episode is sponsored by Full Scale:
https://fullscale.io/

Find out more about Retention.com here:
http://www.retention.com

Learn more about Adam Robinson here:
https://www.linkedin.com/in/retentionadam/

Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz/

Sound Bites
"The best free product I've ever heard of in my life."
"I will make millions of dollars a year, every year."
"Bootstrapping to $10 million ARR will make your product so good."
"Outbound has gotten so weird. Like it's just not as easy as it used to be."
"Using your customers, your satisfied customers to fund your growth."
"Inbound-led outbound, how do we do lead gen, identifying warm leads, and then reaching out to them."

Chapters
00:00 Introduction and Sponsorship
02:20 Adam's Background and RB2B's Launch
04:19 The Value of RB2B's Free Version
07:09 The Billion Dollar Challenge and Realistic Expectations
10:09 The Importance of Simplicity in Product Development
13:07 Balancing Growth and Profitability
14:56 The Downside of Selling a Successful Business
16:51 The Challenges of Managing Rapid Growth
18:53 The Benefits of Owning a Profitable Business
21:14 The Challenges of Scaling Sales and Marketing
24:23 Inbound-Led Outbound Marketing
29:13 Driving Demand through Thought Leadership and Organic Social Media Content
35:22 Engaging in Public Battles and Building a Personal Brand

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Tyler Lieber, co-founder and CEO of Coconut VA, joins Matt Watson on the Startup Puzzle podcast to discuss the benefits and challenges of hiring virtual assistants (VAs) in the Philippines. They share their personal experiences with remote hiring and highlight the importance of trust and communication in working with VAs. Tyler explains that VAs can assist with a wide range of tasks, from email and calendar management to event planning and project coordination. They also discuss the unique advantages of hiring VAs in the Philippines, such as their strong work ethic, English proficiency, and cultural compatibility with US clients. 

Tyler emphasizes the importance of providing competitive pay and benefits to attract and retain top talent. In terms of sales and marketing, Tyler and his team rely heavily on referrals and content marketing to build trust and establish relationships with potential clients. They also discuss the value of strategic delegation and how VAs can help founders become more efficient and focus on high-value tasks. The conversation concludes with a reminder to prioritize work-life balance and take strategic vacations to assess task dependencies and delegate effectively.

Takeaways
Hiring virtual assistants (VAs) in the Philippines offers unique benefits, such as a strong work ethic, English proficiency, and cultural compatibility with US clients.
VAs can assist with a wide range of tasks, including email and calendar management, event planning, project coordination, and more.
Building trust and establishing relationships are crucial in the sales and marketing of VA services, with referrals and content marketing being effective strategies.
Strategic delegation is key to scaling a business and avoiding becoming a bottleneck as a founder.
Taking strategic vacations can help identify tasks that can be delegated to VAs and improve work-life balance.

Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5

This episode is sponsored by Full Scale:
https://fullscale.io/

Find out more about Coconut VA here:
https://www.coconutva.com/cva-linkedin

Learn more about Tyler Leber here:
https://www.linkedin.com/in/tyler-leber/

Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz/

Sound Bites
"If you are hiring an executive assistant, or in this case, what we call a virtual assistant, you are hiring somebody that is just there to help you in whatever possible way that they can."
"The jobs that we are creating for these people are so important to them and so valuable to them, and they're by far some of the best opportunities and best jobs that they will find."
"Referrals are so important in this type of business because really just that trust building and that relationship building is the key to making any sales in this industry."

Chapters
00:00 Introduction and Background
03:00 Starting a Business in the Philippines
06:18 Navigating Business Operations in Another Country
09:07 Training and Mentoring Virtual Assistants
10:50 The Role of Virtual Assistants
14:11 Why the Philippines for Virtual Assistants
18:03 Sales and Marketing Strategies for Virtual Assistant Services
22:43 Target Market and Geographic Reach
29:52 Tips for Hiring and Working with Virtual Assistants

See omnystudio.com/listener for privacy information.

In this episode, Matt Watson interviews Nimrod Vromen, author of Prompting Happiness, about the future of generative AI and its impact on various aspects of life. They discuss the role of lawyers in startups, the importance of focusing on distribution rather than protection in the early stages, and the need for founders to have a clear and comprehensive founders agreement. They also explore the potential of AI in enhancing communication, language translation, and interconnectivity among humans. The conversation delves into the impact of AI on happiness and the importance of self-prompts for personal growth and well-being.

Takeaways
In the early stages of a startup, it is more important to focus on distribution rather than spending a lot of money on legal protection.
Founders should have a clear and comprehensive founders agreement, including reverse vesting, to address potential issues and prevent conflicts.
AI has the potential to enhance communication, language translation, and interconnectivity among humans, but it is important to maintain meaningful connections with other humans.
Self-prompts and a positive approach are essential for personal growth and happiness in the age of AI.

Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5

This episode is sponsored by Full Scale:
https://fullscale.io/

Find out more about Empowerment here:
https://arkempowerment.com/

Learn more about Nimrod Vronen here:
https://www.linkedin.com/in/nimrod-vromen-7378435/

Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz/

Sound Bites
"Entrepreneurs are in a psychotic state. They're supposed to hold the hat and tell the entire world that they're building a billion-dollar business, but they're the only ones who get to peek under the hat and see that it is essentially dead."
"The biggest mistake most founders make is that they don't tell anybody. They're so scared that they don't tell anyone. Worst case scenario, they could have told a few people who might talk to somebody else and introduce them to that person."
"If somebody leaves, they lose the shares they haven't earned. If somebody's let go because the other two let them go for any reason whatsoever, they should lose their equity that they didn't earn."

Chapters
00:00 Introduction and Background
02:09 The Role of Lawyers in Startups
06:07 The Importance of Distribution and Communication
10:21 Founders Agreements and Preventing Conflicts
19:19 The Impact of AI on Happiness and Personal Growth
29:28 The Future of AI and Prompting Happiness

See omnystudio.com/listener for privacy information.

In this episode, Matt Watson and Ian Myers discuss the topic of hiring global talent. Ian shares his experience of starting a company in Sri Lanka and leveraging the highly skilled workforce there. They also discuss the challenges of scaling service-based businesses and the importance of upskilling and mentoring employees. Ian highlights the benefits of hiring talent from different countries and the opportunities it creates for both the employees and the local economies. They also touch on the challenges of running an international business and dealing with local labor laws and government regulations. 

In this conversation, Ian Myers, the founder and CEO of Oceans, and Matt Watson, the founder and CEO of Full Scale, discuss the challenges and strategies involved in running a service-based business. They cover topics such as hiring and firing employees, managing client relationships, and the importance of reputation and referrals. They also emphasize the need for constant evaluation and improvement in recruiting and training processes. Overall, the conversation provides valuable insights into the unique dynamics and considerations of service businesses.

Takeaways
Hiring global talent can provide access to highly skilled professionals from different countries, creating opportunities for both employees and local economies.
Service-based businesses face unique challenges in scaling, but scalable services can be a valuable and profitable business model.
Upskilling and mentoring employees is crucial for their career growth and the success of the company.
Running an international business comes with its own set of challenges, including dealing with local labor laws and government regulations. Running a service-based business involves managing the challenges and dynamics of working with people.
Recruiting and hiring top talent is crucial for the success of a service business.
Maintaining a good reputation and strong client relationships is essential.
Constant evaluation and improvement are necessary in the recruiting and training processes.
Service businesses can be profitable and offer a more predictable income compared to other types of businesses.

Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5

This episode is sponsored by Full Scale:
https://fullscale.io/

Find out more about Oceans XYZ here:
https://oceanstalent.com/

Learn more about Ian Myers here:
https://www.linkedin.com/in/ian-myers-2a997852/

Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz/

Sound Bites
"There's talent everywhere."
"It's weird to make money."
"Scalable services businesses are rare."
"We continue to hire 30 to 40 people a month"
"That's totally normal"
"The Sri Lankan workforce is much more concerned with 401k health insurance, all the benefits"

Chapters
00:00 Introduction to Hiring Global Talent
02:26 The Potential of Global Talent
05:57 Challenges of Scaling Service-Based Businesses
09:57 Hiring American Talent vs. Global Talent
14:12 Investing in Upskilling and Mentoring
19:25 Navigating the Complexities of International Business
25:03 Hiring and Scaling in a Service Business
28:48 The Importance of Benefits and Work Culture in Sri Lanka
33:34 The Key to Success: Hiring and Evaluating Talent
40:05 Firing Clients and Protecting Employees

See omnystudio.com/listener for privacy information.

Chris Callen, founder and CEO of Plot, discusses his journey in the construction technology industry and the challenges of coordinating job sites. He shares his experience with his first software startup and the lessons he learned from it. Callen explains how Plot's job site coordination software helps streamline the delivery and procurement processes in construction. He also discusses the role of AI in the industry and the importance of building trust with customers. The episode concludes with a conversation about the go-to-market strategy for selling software to general contractors.

Takeaways
Job site coordination is a complex process in construction, and software solutions like Plot can help streamline the delivery and procurement processes.
Building trust with customers is crucial in the construction industry, as they are often skeptical of new software solutions.
AI has the potential to make an impact in construction, but it is still in the early stages of adoption.
Trade shows and referrals are effective go-to-market strategies for selling software to general contractors in the construction industry.

Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5

This episode is sponsored by Full Scale:
https://fullscale.io/

Find out more about PLOT here:
https://www.getplot.com/company

Learn more about Chris Callen here:
https://www.linkedin.com/in/chris-callen/

Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz/

Sound Bites
"Plot is a job site coordination software. Primarily we focus on the coordination of who goes where on the site, talking about all of the material deliveries that are coming from all over the planet really, and that are used to make up of any building."
"You obviously need to focus on problem, not solution. We were so infatuated with our solution that we built this, I call it a science project. It was technically pretty amazing. Like what it was able to accomplish was phenomenal, but it didn't solve a business need and it didn't solve something that computed into business value."
"Let's get this out there. Let's see what gets the traction. And by traction, I do mean dollars. I don't mean kind words. I don't mean demonstrations. I mean, who's going to pay for this?"

Chapters
00:00 Introduction to Plot and Job Site Coordination
07:34 Lessons Learned from a Software Startup
15:10 The Role of AI in Construction
19:07 Expanding into Procurement Scheduling
25:23 Building Trust with Customers in the Construction Industry
29:46 Go-to-Market Strategies for Selling Software to General Contractors

See omnystudio.com/listener for privacy information.

David Sinkinson, co-founder of AppArmor, shares his entrepreneurial journey and the lessons he learned along the way. He challenges startup myths and emphasizes the importance of finding the right co-founder. The conversation covers topics such as the need for funding, the psychology of being a founder, the evolution of AppArmor's product, the slow sales cycle in selling to colleges, and the impact of COVID-19 on the business. AppArmor was eventually sold for $40 million. 

The conversation explores the psychology behind valuations and acquisitions in the software business. It highlights the concept of the 'mighty middle' where businesses sell for millions of dollars, but are not the multi-billion dollar giants. The discussion also touches on the challenges and opportunities of building a SaaS company, the importance of timing in seeking funding, and the benefits and complexities of working with family members. The guest also shares insights from his book 'Startup Different' which offers a chronological account of his company's journey and busts 33 myths about entrepreneurship.

Takeaways

• Challenge startup myths and evaluate what is truly necessary for your business.
• Finding the right co-founder who complements your skills and provides support is crucial.
• The evolution of a product is inevitable, and listening to customer feedback is essential for success.
• Selling to colleges can have a slow sales cycle, but once you gain traction, customer loyalty is high.
• Adapting to market changes, such as the impact of COVID-19, requires innovation and listening to customer needs.
• Building a successful business often takes years of hard work and perseverance. The 'mighty middle' refers to businesses in the software industry that sell for millions of dollars, bridging the gap between small startups and multi-billion dollar companies.
• Building a SaaS company to reach a million dollars in revenue is challenging but doable, while reaching 10 million is a whole different level of difficulty.
• Timing is crucial when seeking funding, as it's important for the market to develop and understand the product before investing heavily.
• Working with family members in a business can be successful if there is trust, complementary skills, and effective communication.
• The book 'Startup Different' provides a chronological account of the author's company journey and offers insights and lessons for young entrepreneurs.

Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5

This episode is sponsored by Full Scale:
https://fullscale.io/

Find out more about Startup Different here:
https://www.startupdifferent.com/

Learn more about David Sinkinson here:
https://www.linkedin.com/in/davidsinkinson/

Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz/

Sound Bites

• "We wanted to make sure that entrepreneurs and founders can avoid some of the mistakes that we made."
• "Funding might actually leave your business worse off than if you hadn't pursued it."
• "Being a single founder is hard. You need someone to talk to, cheer with, and pick you back up in the low moments."
• "Most people think of software businesses as being these multi-billion dollar huge sales that happen later coming to nowhere kind of thing."
• "It's relatively easy to build a SaaS company that gets to a million dollars a year in revenue."
• "We were extremely profitable, turning a 60% profit by our final year."

Chapters
00:00 Introduction and Background
04:10 The Importance of Finding the Right Co-founder
07:05 Evolution of a Product: Listening to Customer Feedback
13:09 Navigating the Slow Sales Cycle in Selling to Colleges
15:59 Adapting to Market Changes: The Impact of COVID-19
18:20 Successful Exit: Building a Business Over Time
22:40 Valuations and Acquisitions in the Software Industry
25:17 The Importance of Timing in Seeking Funding
29:43 Taking the Money and Running
31:37 Insights from 'Startup Different' Book

See omnystudio.com/listener for privacy information.

In this episode, Matt Watson interviews Dan Kerr from Flyover Capital, discussing the evolving landscape of venture capital in the Midwest, particularly in Kansas City. They explore the importance of networking for founders, the structure of the upcoming Mid-by-Midwest event, and the changing dynamics of funding, including the rise of debt and royalty financing. 

Dan shares insights on Flyover Capital's investment strategy, the challenges startups face in revenue generation, and the growing variety of investment options available in the region. The conversation highlights the advantages of the Kansas City startup ecosystem and the role of offshore development teams in modern business.

Takeaways
Networking is crucial for founders looking to raise capital.
The Mid-by-Midwest event is designed to connect founders with investors.
Debt and royalty financing are becoming more popular alternatives to equity.
The VC market in 2024 is more selective and cautious than in previous years.
Flyover Capital focuses on investing in undercapitalized regions.
Local investors often take on more risk with Kansas City-based companies.
Startups need to generate revenue to attract investment.
The Kansas City startup ecosystem has evolved significantly over the past decade.
There are now more investment options available for startups in the Midwest.
Offshore development teams are increasingly common among startups.

Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5

This episode is sponsored by Full Scale:
https://fullscale.io/

Find out more about Flyover Capital here:
https://www.flyovercapital.com/

Learn more about Dan Kerr here:
https://www.linkedin.com/in/dankerrkansas/

Sign up for the Startup Hustle newsletter:
https://newsletter.startuphustle.xyz/

Sound Bites
"How much money you got for us today?"
"This is year number three."
"It's a nightmare to reach out to all these different VC companies."

Chapters
00:00 Introduction to the Midwest VC Landscape
03:05 The Importance of Networking for Founders
05:58 Event Format and Structure
09:06 Understanding Debt and Royalty Financing
11:57 The Changing VC Market in 2024
15:05 Flyover Capital's Investment Strategy
18:01 The Role of Local Investors
21:10 Challenges for Startups in Revenue Generation
23:59 The Evolution of the Kansas City Startup Ecosystem
27:00 The Growing Variety of Investment Options
29:51 The Value of Offshore Development Teams
33:05 Conclusion and Event Details

See omnystudio.com/listener for privacy information.