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

Mar 26, 2024 • 56min
Scaling WP Engine with Jason Cohen
Ever felt like your website is about to crash from a sudden surge in traffic?
Our guest founder knows that feeling all too well. In this episode, we chat with the Chief Innovation Officer of WP Engine, Jason Cohen, about the company's incredible journey and his own path from burnt-out developer to successful entrepreneur.
You'll learn:
How Jason's early struggles with WordPress led to the creation of a billion-dollar business.
The surprising secret weapon that helped WP Engine stand out from the crowd (Spoiler alert: probably not the t-shirt).
Why "headless" WordPress is the future and how it can boost your website's performance.
The potential of AI in writing content and creating a more personalized user experience.
How to avoid the "joy and skill trap" and find work that keeps you motivated and energized.
Jason's ingenious interview technique to guarantee a perfect fit for your next hire.
This episode is a must-listen for anyone who:
Runs a WordPress website and wants to take it to the next level.
Dreams of starting their own business but feels stuck on an idea.
Wants to learn how to avoid burnout and find more joy in their work.
Tune in and get ready to be inspired!
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
This episode is sponsored by Full Scale:
https://fullscale.io/
Visit the WP Engine website:
https://wpengine.com/
Learn more about Jason Cohen:
https://www.linkedin.com/in/jasoncohen/
Highlighted Discussion Points
WP Engine and the origin of smart bear with Jason Cohen. 0:32
Starting and selling a successful software company. 1:38
Entrepreneurship and idea validation. 6:16
Growing a WordPress-focused company through marketing strategies. 10:59
Growth strategies for a WordPress hosting company. 13:33
Business strategies and product development in the WordPress industry. 17:10
Decoupling WordPress for better performance and scalability. 22:33
Decoupling, AI, and website components. 25:21
AI and search capabilities in WordPress. 27:47
Company expansion strategies using adjacent markets. 32:58
Evaluating business expansion strategies. 36:00
Entrepreneurship and career development. 39:20
Avoiding burnout and finding joy in work. 46:06
Hiring techniques and avoiding bad fits in the workplace. 49:55
See omnystudio.com/listener for privacy information.

Mar 21, 2024 • 34min
From Car Dealer to Automotive SaaS Leader
Join Matt Watson for a blast-from-the-past reunion with his long-time friend, Danny Zaslavsky! This episode dives deep into Danny's fascinating journey, from growing up in a car dealership to becoming the founder of a tech startup, DealerCue.
Matt and Danny reminisce about their early days working together, the challenges they faced in the car business, and the power of technology to revolutionize the industry. They'll discuss:
The Birth of DealerCue: How Danny's experience managing a car dealership led him to create a revolutionary solution for vehicle lifecycle management.
Entrepreneurship 101: Matt and Danny share their unique stories of building successful companies, from opportunistic beginnings to overcoming generational resistance.
Marketing Magic: Learn how Danny defied traditional advertising strategies and succeeded through community engagement and innovative campaigns.
From Showroom to Startup: Discover how DealerCue leveraged Danny's product expertise to create a game-changing platform.
The Power of Partnership: Matt and Danny reveal the secrets to successful collaborations: trust, complementary skills, and a shared vision.
This episode is packed with valuable insights for anyone interested in entrepreneurship, the ever-evolving car dealership landscape, and the power of partnerships in the tech industry. Tune in and get ready to be inspired!
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
This episode is sponsored by Full Scale:
https://fullscale.io/
Visit the DealerCue website:
https://www.dealercue.com/
Learn more about Danny Zaslavsky:
https://www.linkedin.com/in/danny-zaslavsky-a8503121/
Highlighted Discussion Points
Entrepreneurship journey from car dealership to tech startup. 0:31
Vehicle lifecycle management and DealerCue. 1:21
Entrepreneurship, technology adoption, and generational change in the car dealership industry. 7:16
Advertising and marketing strategies in the car business. 13:02
Marketing and technology in the car dealership industry. 18:20
Entrepreneurship, partnerships, and innovation in the tech industry. 24:39
See omnystudio.com/listener for privacy information.

Mar 19, 2024 • 42min
Pivoting from B2C to B2B, Property Management Tech
Have you ever struggled to find reliable contractors for your home repairs? You're not alone! In this episode, we'll hear from Bo Lais, the CEO and founder of Lula. He started out helping homeowners but discovered a hidden goldmine in the property management industry.
Bo and his wife faced the same challenge as many homeowners: finding qualified contractors. This led them to create a platform to connect homeowners with reliable professionals. But what they learned along the way was even more valuable.
Tune in to hear Bo's story of pivoting his business, the challenges of competing in the property management marketplace, and how Lula ultimately found success by focusing on property management. We'll explore the challenges and triumphs of this strategic shift, including:
Why saying no to a high volume of customers can be the smartest decision
How AI is revolutionizing work order management
The importance of deep integrations with property management software
Successful go-to-market strategies for a niche industry
Building a winning team with core values at the forefront
This episode is packed with valuable insights if you're a property manager, entrepreneur, or someone who's ever battled unreliable contractors.
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
This episode is sponsored by Full Scale:
https://fullscale.io
Visit the Lula website:
https://lula.life
Learn more about Bo Lais:
https://www.linkedin.com/in/bolais
Highlighted Discussion Points
Pivoting from B2C to B2B and the challenges faced. 0:31
Competing with lead generation platforms in the home repair industry. 4:35
Marketplace challenges and pivoting to focus on property management. 7:46
Software development for property management companies. 14:50
Go-to-market strategies for a niche industry. 19:32
Partnerships and business model evolution in property management. 24:08
Focusing on property management services and turning down distracting opportunities. 29:35
Hiring, core values, and growth strategy for a successful tech company. 34:37
Niche business software and software development. 38:05
See omnystudio.com/listener for privacy information.

Mar 14, 2024 • 46min
Career Accelerators, Side Hustles, and LinkedIn Marketing
Tired of dead-end jobs and feeling stuck in your career? Hope is on the horizon.
In this episode, Matt Watson chats with Kadima Careers's Founder, CEO & Chief Accelerator, Alan Stein. Alan, a seasoned professional with a unique career path, shares his insights on:
Fast-tracking your career and exploring side hustles: Learn how Alan went from being "tired of getting fired" to helping others land their dream jobs, and explore his experiences on both sides of the interview table.
Crafting a winning job search strategy: Discover Alan's proven methods for identifying target companies, navigating the application process, and securing top offers.
Building a successful business: Get an inside look at Alan's journey from corporate employee to full-time entrepreneur, including the challenges and rewards of building a thriving business.
Leveraging LinkedIn for professional growth: Learn how Alan utilizes LinkedIn to connect with potential clients, build relationships, and grow his business.
Tune in for actionable advice, inspiring stories, and practical tips to take your career and business to the next level!
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
This episode is sponsored by Full Scale:
https://fullscale.io
Visit the Kadima Careers website:
https://kadimacareers.com
Learn more about Alan Stein:
https://www.linkedin.com/in/alanjstein
Highlighted Discussion Points:
Career acceleration and side hustles with Kadima Careers founder Alan Stein. 0:32
Career growth and job placement. 1:24
Career coaching and job search strategies. 8:44
Transitioning from corporate to full-time business ownership. 13:56
Building a startup, scaling up, and using virtual assistants. 19:51
Leveraging LinkedIn for business growth. 25:52
Leveraging LinkedIn for business growth. 31:07
LinkedIn ads and international business strategies. 37:20
See omnystudio.com/listener for privacy information.

Mar 12, 2024 • 44min
The Value of Product Teams
Do you feel lost in the world of product development? Are you struggling to gain traction, validate your idea, or build a team that delivers?
In this episode, we're joined by Adam Judelson, founder and CEO of First Principles Catalyst, to dissect the common problems tech companies face with product development. From the challenges of early-stage startups to building the right product team, Adam brings his wealth of experience.
Matt and Adam have an uber-dynamic conversation on the following topics:
The importance of a product team and how it can supercharge your success.
Why focus is key, and how to navigate product management challenges.
How to validate your product idea before pouring resources into development.
The entrepreneurial mindset and the dangers of ignoring reality.
When to bring in outside help and how to find the right product agency partner.
Building a high-performing product team, including hiring tips and understanding the roles of product owners, product ops, and engineers.
The importance of collaboration and diverse perspectives in creating world-changing products.
Whether you're a seasoned entrepreneur or just starting your journey, this episode is packed with actionable insights and practical advice to help you build products that win.
So, tune in and get ready to learn the value of product teams for your company!
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
This episode is sponsored by Full Scale:
https://fullscale.io
Visit the First Principles Catalyst website:
https://www.firstprinciples.la
Learn more about Adam Judelson:
https://www.linkedin.com/in/adam-judelson/
Highlighted Discussion Points
Product problems in tech companies with a product agency founder. 0:31
Product management and its challenges. 1:56
Product development for early-stage startups with limited funding. 7:08
Entrepreneurial mindset and honesty in startups. 12:24
Founders' reluctance to ask for help in their startups. 15:21
When to hire a full-time product person for an early-stage company. 17:03
Hiring for product management roles in startups. 22:17
See omnystudio.com/listener for privacy information.

Mar 7, 2024 • 47min
Product Strategy SMB vs Enterprise
Ever wonder how to create a product that caters to both small businesses and giant corporations?
Join Matt Watson as he dives deep into the world of product strategy with Jeff Weiner, CEO of Realquantum. Discover how the company revolutionized commercial real estate appraisal software and the crucial differences in catering to small and medium-sized businesses (SMBs) vs. enterprise giants.
They dive deep into Jeff's journey, from recognizing the industry's need for innovation to building a platform that revolutionizes the way commercial real estate appraisals are done.
This episode is packed with insights on:
Adapting your product strategy for diverse customer segments
Navigating the challenges of enterprise integration
Balancing simplicity with advanced features for a smooth user experience
The importance of saying "no" to bad product ideas
Whether you're a startup founder or a seasoned software developer, this episode is guaranteed to equip you with valuable knowledge for tackling the ever-evolving landscape of product development!
Tune in, learn, and conquer the market!
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
This episode is sponsored by Full Scale:
https://fullscale.io/
Visit the Realquantum website:
https://www.realquantum.com
Learn more about Jeff Weiner:
https://www.linkedin.com/in/jeffreyweiner
Highlighted Discussion Points
Product strategy for startups with Jeff Weiner. 0:32
Commercial real estate appraisal software and its potential to revolutionize the industry. 1:19
Product strategy and market research for a real estate tech company. 7:05
Appraisal software development and market needs. 13:18
Catering to enterprise and small business needs in software development. 19:43
Enterprise software development challenges and solutions. 24:39
Adapting product strategy for enterprise vs. SMB customers. 29:30
Simplifying software for appraisers without overcomplicating it. 34:55
Enterprise software development challenges and solutions. 38:59
See omnystudio.com/listener for privacy information.

Mar 5, 2024 • 37min
Tech's Impact on Modern Sales
Ever wonder how top brands create ads that resonate with you on a personal level? In this episode of Startup Hustle, Matt Watson dives into AI-powered marketing with Matt Swalley, Co-founder and Chief Business Officer of Omneky.
Discover how Omneky's platform leverages cutting-edge AI to:
Craft hyper-personalized ads: Target different age groups, cultures, and individuals with tailored messages that resonate.
Generate and optimize ad creatives: Unleash the power of AI to test and refine your ad content for maximum impact, even with limited budgets.
Automate ad buying and management: Free up your time and resources by letting AI handle tedious tasks across platforms like LinkedIn and Meta.
Matt and Matt also discuss:
The evolution of AI technology, including the impact of GPT-3 and GPT-4 on Omneky's platform.
The future of AI-powered content creation, from image generation to video production.
How agencies and brands can leverage AI to scale their marketing efforts and personalize the customer journey.
Join us as we explore the exciting possibilities of AI in marketing and discover how it can help your business thrive!
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
This episode is sponsored by Full Scale:
https://fullscale.io
Visit the Omneky website:
https://www.omneky.com
Learn more about Matt Swalley:
https://www.linkedin.com/in/matt-swalley-59249533
Highlighted Discussion Points:
AI and marketing with Omneky founder Matt Squally. 0:32
AI-powered ad generation and personalization. 1:21
AI-powered ad creative optimization. 6:02
AI-powered ad creative generation for various businesses. 11:59
AI-powered content creation and its future. 17:20
Marketing strategies and AI-generated content. 22:50
Digital advertising, sales, and marketing strategies. 29:03
See omnystudio.com/listener for privacy information.

Feb 29, 2024 • 41min
Innovating With the Grain World’s First Bulk Solids Locomotion Device
Forget drones, the future swims!
Imagine a world where robots don't fly, they dive - not through water, but through mountains of sand, grains, and powders. This isn't science fiction, it's the reality being built by Lorenzo Conti, the engineer behind a revolutionary technology. Join Matt Watson as he digs deep into the technology behind moving through "granular materials" with unprecedented efficiency.
In this episode, we dive headfirst (pun intended!) into Lorenzo's fascinating journey:
From discovering a hidden connection between physics and sand to creating the world's first "Dune"-worthy sand swimmer.
Navigating the challenges of changing entire industries, one grain at a time.
Unveiling the secrets of movement in unpredictable environments, paving the way for a future of automated grain management.
Exploring the future of robotics, where robots become platforms for customization and collaboration.
And finally, challenging the status quo of international patent protection in the age of innovation.
Join us as we uncover the secrets of the "granular world" and explore the future of technology that literally swims through it!
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
This episode is sponsored by Full Scale:
https://fullscale.io
Visit the Crover website:
https://www.crover.tech
Learn more about Lorenzo Conti:
https://www.linkedin.com/in/lconti
Highlighted Discussion Points:
Building robots to swim through grain with Crover founder Lorenzo Conti. 0:31
Entrepreneurship, innovation, and technology in Scotland. 1:35
Using AI to monitor grain quality and safety. 6:57
Using sensors to monitor grain quality. 11:46
Designing and manufacturing a robot for harvesting grain. 17:49
Developing a robotic system for grain storage inspection. 25:26
The patent filing process for a unique physical device. 31:54
Entrepreneurship, technology, and the future of work. 37:04
See omnystudio.com/listener for privacy information.

Feb 27, 2024 • 43min
Automotive Technology & Digital Retailing
Join host Matt Watson as he goes into the complex world of automotive technology with a twist of entrepreneurial spirit. In this episode, Matt sits down with the innovative mind behind WebBuy and the visionary founder of Pauldron, CTO Steve Dimock.
Buckle up as they traverse through the rugged landscapes of Montana, exploring the untamed frontier of tech industry growth. From the emergence of pioneering companies like Onyx to the burgeoning computer science programs igniting young minds, Montana's tech scene is a force to be reckoned with.
Unveil the challenges of crafting an online car-buying platform with Steve Dimock, where the scarcity of software talent in Kansas is just the tip of the iceberg. Dive deep into the complexities of digital retailing solutions and the quest for transparency in the automotive realm.
Explore the innovative strategies employed by WebBuy and Pauldron to revolutionize the car buying process, promising not just efficiency, but a newfound trust between dealerships and consumers. Discover how they're slashing dealership wait times and reshaping the very fabric of automotive retail.
Peel back the layers of technological ingenuity as Matt and Steve dissect the AI-powered revolution in vehicle service contracts. From personalized recommendations to seamless follow-ups, witness the future of automotive maintenance unfold before your eyes.
And don't miss out on the riveting tale of Steve Dimock's latest venture, Pauldron, where partnerships pave the road to success and experience meets innovation head-on.
Tune in as Matt Watson and Steve Dimock navigate the fast lanes of tech entrepreneurship, leaving no stone unturned in their quest to reshape the automotive landscape, one byte at a time.
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
This episode is sponsored by Full Scale:
https://fullscale.io/
Visit the WebBuy website:
https://webbuy.com/
Visit the Pauldron website:
https://pauldron.net/
Learn more about Stephen Dimock
https://www.linkedin.com/in/sdimock/
Highlighted Discussion Points
Automotive tech and startup WebBuy and Pauldron with CTO Steve Dimock. 0:01
Tech industry growth in Montana. 1:03
Challenges in creating an online car-buying platform. 2:19
The complexity of car buying process and digital retailing solutions. 6:11
Car buying process and software to improve trust and efficiency. 9:51
Digital retailing for car dealerships. 14:51
Digital retailing adoption in the automotive industry. 21:28
Automotive digital retailing and new company Pauldron. 26:35
AI-powered vehicle service contract follow-up system. 31:25
Go-to-market strategy for a new venture. 36:45
See omnystudio.com/listener for privacy information.

Feb 22, 2024 • 42min
Navigating the Future Tech in Asphalt Paving
Ever wondered how tech is transforming the dusty world of paving and construction? Join us on the podcast as we chat with Bryce Wuori, CEO of PaveWise, who turned a family business into a cutting-edge tech company!
Here's what you'll learn:
From asphalt to algorithms: How Bryce pivoted a traditional business and tackled industry challenges with software solutions.
Weathering the storm: Discover how PaveWise uses AI to predict and avoid costly weather disruptions, saving businesses time and money.
Bootstrapped to VC-backed: Get the inside scoop on building a tech startup from scratch, including funding strategies and scaling with an offshore team.
Idea bucket or chaos vortex? Learn how PaveWise manages innovation in a fast-paced environment, prioritizing the right ideas for success.
Customer-first: From building for themselves to listening to users, understand how PaveWise adapts and delivers value.
From dusty boots to trade shows: Uncover PaveWise's unique go-to-market strategy for connecting with clients in the real world.
Ready to pave the way to your own success? Tune in to the podcast and get inspired by Bryce Wuori's story!
Find Startup Hustle Everywhere:
https://gigb.co/l/YEh5
This episode is sponsored by Full Scale:
https://fullscale.io/
Visit the PaveWise website:
https://pavewisepro.com/
Learn more about Bryce Wuori
https://www.linkedin.com/in/bryce-w-89818b237/
Highlighted Discussion Points:
Paving technology and construction with the CEO of PaveWise. 0:00
Paving industry challenges and software solutions. 1:05
Weather impacts on construction work and proactive planning. 4:34
Construction software development and entrepreneurship. 8:56
Scaling a tech startup with a CTO. 15:31
Managing and prioritizing ideas in a fast-paced startup environment. 23:46
Entrepreneurship, product development, and customer feedback. 27:00
Software development challenges and sales strategies. 32:32
Go-to-market strategies for tech companies. 36:56
See omnystudio.com/listener for privacy information.