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.TakeawaysJob 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/YEh5This episode is sponsored by Full Scale:https://fullscale.io/Find out more about PLOT here:https://www.getplot.com/companyLearn 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?"Chapters00:00 Introduction to Plot and Job Site Coordination07:34 Lessons Learned from a Software Startup15:10 The Role of AI in Construction19:07 Expanding into Procurement Scheduling25:23 Building Trust with Customers in the Construction Industry29:46 Go-to-Market Strategies for Selling Software to General ContractorsSee 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/YEh5This 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." Chapters00:00 Introduction and Background04:10 The Importance of Finding the Right Co-founder07:05 Evolution of a Product: Listening to Customer Feedback13:09 Navigating the Slow Sales Cycle in Selling to Colleges15:59 Adapting to Market Changes: The Impact of COVID-1918:20 Successful Exit: Building a Business Over Time22:40 Valuations and Acquisitions in the Software Industry25:17 The Importance of Timing in Seeking Funding29:43 Taking the Money and Running31:37 Insights from 'Startup Different' BookSee 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. TakeawaysNetworking 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." Chapters00:00 Introduction to the Midwest VC Landscape03:05 The Importance of Networking for Founders05:58 Event Format and Structure09:06 Understanding Debt and Royalty Financing11:57 The Changing VC Market in 202415:05 Flyover Capital's Investment Strategy18:01 The Role of Local Investors21:10 Challenges for Startups in Revenue Generation23:59 The Evolution of the Kansas City Startup Ecosystem27:00 The Growing Variety of Investment Options29:51 The Value of Offshore Development Teams33:05 Conclusion and Event DetailsSee omnystudio.com/listener for privacy information.

In this episode, Matt Watson interviews Michelle Denogean, the Chief Marketing Officer of MindTrip and author of the book 'Grow Up.' They discuss the challenges that founders face when growing their companies and the importance of having a diverse team with different superpowers. Michelle introduces four superpowers: innovator, builder, connector, and persuader, and explains how each one contributes to the growth of a company. They also talk about the blind spots that come with each superpower and the need for self-awareness and trust in delegating tasks to others. Michelle offers advisory services to help founders reflect on their leadership styles and guide them in building the right team and positioning their brand.TakeawaysThe superpowers of founders are not always the same as the roles they play in their companies.Each superpower comes with its own blind spots and weaknesses.Successful growth requires embracing the strengths of others and building a diverse team.Self-awareness is crucial for recognizing blind spots and understanding the value of different superpowers.Trust is essential in delegating tasks and empowering team members.Having the right people around you is the key to overcoming challenges and achieving growth.Reflecting on your own leadership style and understanding your weaknesses can help you become a better leader.Pivoting and adapting to market needs is important for the success of a startup.The cure to startup failure is the people you have around you.Being aware of your own strengths and weaknesses can help you make better decisions and focus on what you truly enjoy.titlesFocusing on Your Strengths and Enjoying the JourneyThe Importance of Pivoting and Adapting to Market Needs Find Startup Hustle Everywhere:https://gigb.co/l/YEh5This episode is sponsored by Full Scale:https://fullscale.io/Find out more about Mindtrip here:https://mindtrip.ai/ Learn more about Michelle Denogean here:https://www.linkedin.com/in/michelledenogean/ Sign up for the Startup Hustle newsletter:https://newsletter.startuphustle.xyz/ Sound Bites"The superpowers of founders are not always the same as the roles they play in their companies.""Successful growth requires embracing the strengths of others and building a diverse team.""Trust is essential in delegating tasks and empowering team members."Chapters00:00 Introduction and Overview11:48 The Superpowers of Founders and the Challenges of Growth18:37 The Importance of Building a Diverse Team with Different Superpowers25:18 Recognizing Blind Spots and Embracing the Strengths of Others30:08 The Role of Trust in Delegating Tasks and Empowering Team Members35:01 Overcoming Challenges and Achieving Growth with the Right People38:16 Reflecting on Your Leadership Style and Understanding Your Weaknesses38:40 Becoming a Better Leader Through Self-Awareness and ReflectionSee omnystudio.com/listener for privacy information.

In this episode, Matt Watson interviews Markus Waite, the President of Empara and CIO of Goodroot, about healthcare technology. They discuss the challenges and complexities of the healthcare industry, the role of generative AI in simplifying healthcare processes, the high cost of healthcare in the United States, and the need for transparency and cost-saving solutions. Marcus also shares insights into the work of Goodroot, a company that focuses on solving healthcare problems through innovative solutions and a portfolio of affiliate companies. TakeawaysHealthcare is a complex industry with many systems and processes that need to be reinvented to improve the overall experience.Generative AI has the potential to be a game-changer in healthcare, simplifying processes and providing curated responses to help individuals navigate their healthcare journey.The high cost of healthcare in the United States is a significant challenge, and there is a need for transparency and cost-saving solutions.Goodroot is a company that focuses on solving healthcare problems through innovative solutions and a portfolio of affiliate companies. Find Startup Hustle Everywhere:https://gigb.co/l/YEh5 This episode is sponsored by Full Scale:https://fullscale.io/ Find out more about Empara here:https://www.empara.io Learn more about Markus Waite here:https://www.linkedin.com/in/markuswaite/ Sign up for the Startup Hustle newsletter:https://newsletter.startuphustle.xyz/ Sound Bites"Our mission is reinventing healthcare one system at a time.""Generative AI is a game-changer. We've officially drank the Kool-Aid.""The high cost of healthcare is a significant challenge, and there is no incentive to make it less expensive." Chapters00:00 Introduction to Marcus Waite and Goodroot02:15 The Evolution of Healthcare Technology06:38 The High Cost of Healthcare in the United States10:12 Empowering Employees to Make Informed Healthcare Decisions16:56 Overview of Goodroot and its Innovative Solutions21:08 Selling Healthcare Technology Solutions23:03 Building Technology in the Healthcare Industry30:13 The Need for Transparency and Cost-Saving SolutionsSee omnystudio.com/listener for privacy information.

In this episode, Matt Watson interviews Keith Harrington, the founder and COO of Novel Capital, about non-dilutive capital and alternative funding options for startups. They discuss the different types of capital available, such as revenue-based financing and venture debt, and the importance of understanding when and how to raise money. Keith emphasizes the need for entrepreneurs to have access to information, capital, and tools to make informed financing decisions. They also touch on the risks of raising too much equity and the benefits of practical, sustainable growth. Takeaways- Non-dilutive capital, such as revenue-based financing and venture debt, provides alternative funding options for startups.- Entrepreneurs should carefully consider their use of funds and choose the right type of financing that aligns with their growth plans.- Raising too much equity can lead to high valuations and potential dilution of ownership, making it important to be mindful of the long-term implications.- Understanding the repayment structure, cost of capital, and potential risks associated with different financing options is crucial for making informed decisions.- Tools like Novel Capital's venture match can help entrepreneurs connect with equity investors based on their underlying business dynamics. Find Startup Hustle Everywhere:https://gigb.co/l/YEh5  This episode is sponsored by Full Scale:https://fullscale.io/  Find out more about Novel Capital here:https://novelcapital.com/ Learn more about Keith Harrington here:https://www.linkedin.com/in/keithharringtonkansas/  Sign up for the Startup Hustle newsletter:https://newsletter.startuphustle.xyz/  Sound Bites"The most important part of it is actually sales and marketing.""Let's just start with what are you trying to accomplish. And then let's point you to the product that makes the most sense.""Most people don't think about the downside of all of those." Chapters00:00 Introduction and Overview03:10 Understanding the Service Offering and Target Audience05:48 The Creation of Tools to Assist Entrepreneurs08:17 The Importance of Sales and Marketing in Building a Business10:08 The Challenges of Traditional Banks and the Need for Alternative Financing12:02 Exploring Different Financing Options and Use Cases15:13 The Role of Introductions to Venture Capital Firms17:50 The Shift in Mindset Regarding Raising Venture Capital20:35 The Risks of Raising Too Much Equity23:30 The Benefits of Practical Growth and Bootstrapping25:14 The Availability and Accessibility of Debt Financing29:01 The Differences Between Debt Financing and Equity Financing31:23 Considerations and Red Flags When Choosing a Financing Provider34:00 Novel Capital's Tools and Venture Match PlatformSee omnystudio.com/listener for privacy information.

Christian Hammer, founder and CEO of Vala AI, joins Matt Watson on the Startup Hustle podcast to discuss AI for software development and the concept of technical debt. They explore the challenges of bridging the gap between business needs and technology, the different definitions of tech debt, and the importance of keeping up with the rate of change in the industry. Christian shares insights into Vala AI's platform, which aims to provide a holistic view of an organization's tech stack and help identify and address tech debt. Takeaways- Tech debt is the gap between business needs and the technology that supports those needs.- Off-the-shelf software often has inherent tech debt because it is not custom-built for specific use cases.- The rate of change in technology is accelerating, leading to an accumulation of tech debt.- The term 'technical debt' can be misleading and should be replaced with more accurate terminology.- AI in software development is still in its early stages and should be treated as a junior engineer or intern.- Effective communication and understanding between business and technology teams is crucial to address tech debt. Find Startup Hustle Everywhere:https://gigb.co/l/YEh5 This episode is sponsored by Full Scale:https://fullscale.io/ Find out more about Vala AI here:https://www.vala-ai.com/ Learn more about Christian Hammer here:https://www.linkedin.com/in/chammer1/ Sign up for the Startup Hustle newsletter:https://newsletter.startuphustle.xyz/ Sound Bites"Tech debt is the gap between business needs and the technology that supports those needs.""All software that we build over time will eventually be replaced or go away.""The evil technical debt is the one that is brutal and prevents you from doing other things." Chapters00:00 Introduction and Background01:30 The Origin of Vala AI and the Problem of Tech Debt07:27 The Accelerating Rate of Change and Tech Debt Accumulation10:43 The Need for Better Terminology and Definitions14:28 The Role of Effective Communication in Addressing Tech Debt25:06 The Importance of Understanding Business Needs and Possibilities29:14 Vala AI's Platform and Approach to Addressing Tech Debt32:00 The Current State of AI in Software Development36:16 Differentiating Between Software Engineers and Coders37:46 Vala AI's Mission and PodcastSee omnystudio.com/listener for privacy information.

In this episode, Matt Watson and Ryan Dowdy discuss the difference between professional service companies and SaaS companies. They explore the challenges and opportunities of scaling a service-based business and the importance of sales and distribution in entrepreneurship. They also touch on the significance of personal branding for founders and the role it plays in building trust and thought leadership. The conversation focuses on the importance of values alignment, personal branding, and quality in business growth. They discussed how values alignment with customers and clients can lead to stronger relationships and referrals. They also emphasized the power of personal branding in building trust and attracting customers. The conversation touched on the significance of storytelling and transparency in marketing, as well as the challenges and rewards of running service companies versus SaaS companies. Finally, they highlighted the importance of quality and customer satisfaction in driving referrals and long-term success. TakeawaysProfessional service companies and SaaS companies have different business models and growth strategies.Scaling a service-based business can be challenging, but it offers opportunities for growth and scalability.Sales and distribution are crucial for the success of any business, regardless of its industry.Personal branding is becoming increasingly important for founders and entrepreneurs to establish thought leadership and build trust. Values alignment with customers and clients is crucial for building strong relationships and driving referrals.Personal branding can help establish trust and attract customers who align with your values.Storytelling and transparency in marketing can be more effective than generic marketing messages.Running a service company can be less risky and easier to get off the ground compared to a SaaS company.Quality and customer satisfaction are key drivers of referrals and long-term success. Find Startup Hustle Everywhere:https://gigb.co/l/YEh5 This episode is sponsored by Full Scale:https://fullscale.io/ Sign up for the Startup Hustle newsletter:https://newsletter.startuphustle.xyz/ Sound Bites"We are a software development company. We help other people, but it's totally different. Like I'm not writing the code. I don't do any of the work.""Overall, only 1% of companies make it to 10 million. That's a giant accomplishment.""Valuations of SaaS companies tend to be tied to top line revenue, while service companies are valued based on EBITDA.""Do my values align with the person I'm doing business with?""The number one driver of sales for most companies is referrals.""You don't control referrals, but they just happen." Chapters00:00 Introduction and Overview02:30 Difference Between Professional Service Companies and SaaS Companies05:49 Challenges and Opportunities of Scaling a Service-Based Business12:58 Significance of Personal Branding for Founders and Entrepreneurs23:39 Values Alignment and Business Success26:55 The Unpredictability of Referrals33:18 Quality as a Cornerstone of Business GrowthSee omnystudio.com/listener for privacy information.

In this episode, Matt Watson and Brett Sears discuss the importance of customer onboarding and training in software companies. They highlight the need for software companies to focus on getting customers to see value and have an 'aha' moment as quickly as possible. They also emphasize the significance of understanding the perspective of new users and providing a seamless onboarding experience.  The discussion delves into the evolving landscape of user onboarding and customer success, highlighting the shift towards concise, value-driven content and intuitive software design. It emphasizes the crucial role of the adoption funnel in guiding users from initial onboarding through engagement and expansion while underscoring the importance of customer success teams in reducing churn and fostering referrals. The conversation explores the ongoing need for effective product marketing and introduces two platforms, Adopt IQ and Sequence, designed to enhance user adoption and deliver dynamic content. Throughout, the focus remains on providing quick value to users, creating user-friendly experiences, and implementing strategies to improve adoption rates, reduce customer churn, and drive expansion revenue in today's fast-paced software environment. Takeaways- Customer onboarding and training are crucial for software companies to ensure that customers see value and have an 'aha' moment as quickly as possible.- Understanding the perspective of new users and providing a seamless onboarding experience is essential for customer success.- Reducing churn and increasing expansion revenue are key goals for software companies.- Complex software cannot be intuitive, but it can be made more approachable through user-centric design and support.- Micro videos and in-application help can be effective tools for onboarding and training. Short videos and concise content are becoming increasingly popular as users seek quick answers and value.- Software should be intuitive and user-friendly, allowing users to execute tasks without extensive training.- The adoption funnel, consisting of onboarding, engagement, and expansion, is crucial for guiding users through different stages and ensuring their success.- Customer success plays a vital role in reducing churn and driving referrals.- Ongoing product marketing is essential for keeping users engaged and driving adoption.- Adopt IQ and Sequence are two platforms that aim to enhance user adoption and provide dynamic content. Find Startup Hustle Everywhere:https://gigb.co/l/YEh5 This episode is sponsored by Full Scale:https://fullscale.io/ Find out more about AdoptIQ here:https://link.traininglayers.com/LI2R Learn more about Bret Siers here:https://www.linkedin.com/in/bret-siers-%E2%96%B6/ Sign up for the Startup Hustle newsletter:https://newsletter.startuphustle.xyz/ Sound Bites"Recurring revenue requires recurring value.""Figuring out the 'aha' moments is half the battle.""The first question is, do I have any idea what I'm doing?""Now I think that's changed. That means that they're not getting the answer fast enough.""Nobody wants to watch a 20-minute video.""I think 80% of the people shouldn't learn how to use software. They should be able to execute on it." Chapters00:00 Introduction and Importance of Customer Onboarding03:27 Understanding the Perspective of New Users06:32 Reducing Churn and Increasing Expansion Revenue12:01 Making Complex Software Approachable15:01 Using Micro Videos and In-Application Help for Onboarding22:49 The Importance of User-Friendly Software28:28 The Role of Customer Success in Reducing Churn and Driving Referrals31:34 The Significance of Ongoing Product Marketing35:25 Introducing Adopt IQ and Sequence: Enhancing User Adoption and Providing Dynamic ContentSee omnystudio.com/listener for privacy information.

In this episode, Matt Watson and Ryan Dowdy discuss the importance and benefits of being recognized on the Inc 5000 list. They explore the motivations behind winning awards and the impact it has on company culture, employee morale, and recruiting. They also highlight the value of third-party validation and how it builds credibility and trust with customers and investors. The conversation emphasizes the significance of celebrating wins and the role of awards in showcasing a company's success. TakeawaysBeing recognized on the Inc 5000 list provides third-party validation and builds credibility and trust with customers and investors.Winning awards can boost company culture, employee morale, and recruiting efforts.Celebrating wins is important and often overlooked in the fast-paced world of entrepreneurship.Awards and accolades serve as a marketing tool and give companies a reason to reach out to existing customers and potential clients.The Inc 5000 list is attainable for companies that have experienced significant growth over a three-year period.Applying for awards and nominations can be a strategic play to position a company as an industry leader. Find Startup Hustle Everywhere:https://gigb.co/l/YEh5 This episode is sponsored by Full Scale:https://fullscale.io/ Sign up for the Startup Hustle newsletter:https://newsletter.startuphustle.xyz/ Sound Bites"We don't stop enough and give credit to the team and the whole company. Let's stop and celebrate as a company. If we did this big thing as a team, this is a team sport.""People want to do business with winners. We all have that bias. We all want to win.""Recruiting is a huge issue. Good people want to be part of winning teams and winning companies." Chapters00:00 Introduction and Background02:38 Celebrating Wins and Recognizing the Team07:16 The Impact of Awards on Company Culture and Recruiting09:45 The Value of Being Recognized as a Winner11:30 The Role of the Founder as a Cheerleader15:43 The Inc 5000 as a Favorite AchievementSee omnystudio.com/listener for privacy information.