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This is a short-form solo episode, where Ryan breaks down the differences between VC-backed and bootstrapped companies so you can understand how to create revenue from them, their motivators and more in a simple, easy-to-understand way.
KEY TAKEAWAYS
BEST MOMENTS
“I have clients on both sides, and I interview people on both sides”
“If you’re selling to these types of companies, if you can do more with less or show them that more for less philosophy this is going to get them really excited”
“I’ve never seen such a heavy focus on stock price”
Do You Want The Closing Secrets That Helped Close Over $125 Million in New Business for Free?" Grab them HERE: https://www.whalesellingsystem.com/closingsecrets
Ryan Staley
Founder and CEO
Whale Boss
312-848-7443
www.ryanstaley.io
EPISODE RESOURCES
ABOUT THE SHOW
How do you grow like a VC-backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Andrew Gazdecki (Founder of Micro Acquire), Harpal Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.
This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets
Ryan is joined by the co-founder and CEO of NFT-based SaaS product Pinata, Kyle Tut. Kyle has a background in blockchain development and was previously the operations chief at RaceNote where he was responsible for developing management processes for products.
Kyle talks to Ryan about his journey into a technical space as a non-technical founder and his step-by-step approach to this. Kyle also gives some good tips on how to create and nurture relationships built on trust and respect with an audience/client base that is more complicated and sceptical than the average.
KEY TAKEAWAYS
BEST MOMENTS
“Developers are much different to traditional business or consumer relationships”
“I had always known that I wanted to build my own company”
“I was lucky to be there in the space at the time”
“As a non-technical person, it is difficult to learn how to meet technical people”
“We’re finding a lot of success in our long-form content”
Do You Want The Closing Secrets That Helped Close Over $125 Million in New Business for Free?" Grab them HERE: https://www.whalesellingsystem.com/closingsecrets
Ryan Staley
Founder and CEO
Whale Boss
312-848-7443
www.ryanstaley.io
EPISODE RESOURCES
https://www.linkedin.com/in/kyletut/
ABOUT THE SHOW
How do you grow like a VC-backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Andrew Gazdecki (Founder of Micro Acquire), Harpal Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.
This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets
This is a rare solo episode from Ryan! Ryan has taken some time to reflect on over 100 CEO interviews over the past year and wanted to share the TOP 6 takeaways from them with you all.
KEY TAKEAWAYS
BEST MOMENTS
“Every interview struggles massively at points in their life”
“There’s not one single cheat code for growth”
“My eyes have been opened to things and areas I didn’t even know existed”
Do You Want The Closing Secrets That Helped Close Over $125 Million in New Business for Free?" Grab them HERE: https://www.whalesellingsystem.com/closingsecrets
Ryan Staley
Founder and CEO
Whale Boss
312-848-7443
www.ryanstaley.io
ABOUT THE SHOW
How do you grow like a VC-backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Andrew Gazdecki (Founder of Micro Acquire), Harpal Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.
This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets
Ryan is joined by the CEO and founder of Tint, Matheus Riolfi. Matheus talks about how to add margin to SaaS projects in a unique, yet simple way and explains how you can do this with your business too. He also talks about his journey to becoming a founder and how to gain funding early on in a start-up. Listen in to learn more including how Riolfi is using Tint to democratise the insurance industry through the power of AI.
KEY TAKEAWAYS
BEST MOMENTS
“Typical founder journey, it’s never linear”
“We are a plug-and-play product”
“Our challenge is definitely how to scale our business at this stage”
Do You Want The Closing Secrets That Helped Close Over $125 Million in New Business for Free?" Grab them HERE: https://www.whalesellingsystem.com/closingsecrets
Ryan Staley
Founder and CEO
Whale Boss
312-848-7443
www.ryanstaley.io
EPISODE RESOURCES
https://www.linkedin.com/in/mriolfi/
ABOUT THE SHOW
How do you grow like a VC-backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Andrew Gazdecki (Founder of Micro Acquire), Harpal Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.
This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets
Simha is the CEO and co-founder of Ushur, a service engagement platform that leverages data and tech to digitally transform backend processes for industries that struggle with customer service.
Simha talks to Ryan about his journey through entrepreneurship, including his experience in running $ 100 million revenue companies, and consulting and scaling teams. He explains how he and his team have created a new category within the SaaS space with their unique customer experience automation product and how he bootstrapped his way to gaining fortune 500 companies as clients before gaining VC backing. He also sheds light on what he believes the future of tech to be.
KEY TAKEAWAYS
BEST MOMENTS
“We built a horizontal platform with a vertical go-to-market strategy”
“Having discipline and focus allows you to run a long race”
“Many things in life are serendipity and accidental”
Do You Want The Closing Secrets That Helped Close Over $125 Million in New Business for Free?" Grab them HERE: https://www.whalesellingsystem.com/closingsecrets
Ryan Staley
Founder and CEO
Whale Boss
312-848-7443
www.ryanstaley.io
EPISODE RESOURCES
https://www.linkedin.com/in/simhasadasiva/
ABOUT THE SHOW
How do you grow like a VC-backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Andrew Gazdecki (Founder of Micro Acquire), Harpal Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.
This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets
Ryan is joined by Ryan Buick, co-founder of Canvas app. He talks through the hyper-short process he used to get funding from one of the largest VCs in the world. Ryan also explains how he and his team are democratising the need to transform your data into measurable business results alongside solving the many problems of a data-backed world.
KEY TAKEAWAYS
BEST MOMENTS
“It’s all lip service until you start actually getting people to pay for it”
“Most people are still going to rely on spreadsheet skills”
“They have all the data they need but they aren’t leveraging the insights they have”
Do You Want The Closing Secrets That Helped Close Over $125 Million in New Business for Free?" Grab them HERE: https://www.whalesellingsystem.com/closingsecrets
Ryan Staley
Founder and CEO
Whale Boss
312-848-7443
www.ryanstaley.io
EPISODE RESOURCES
www.canvasapp.com
ABOUT THE SHOW
How do you grow like a VC-backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Andrew Gazdecki (Founder of Micro Acquire), Harpal Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.
This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets
Matt Blumberg is the co-founder and CEO of the senior executive marketplace Bolster. Matt has written three books including ‘The Start-Up CEO’ and created the 2nd best company to work for in the USA, due to the culture he developed.
He talks to Ryan in this episode about how the Bolster marketplace connects CEOs, start-ups and scale-ups with senior executives as well as breaks down his framework for what you can do to create a great culture and high-performing team.
KEY TAKEAWAYS
BEST MOMENTS
“Any way that we can help a start-up be more successful by scaling their leadership team, their CEO’s capabilities or scaling their board we are the place to come”
“Bolster are changing the way people look for executive talent”
“You can hire a senior executive to do anything”
Do You Want The Closing Secrets That Helped Close Over $125 Million in New Business for Free?" Grab them HERE: https://www.whalesellingsystem.com/closingsecrets
Ryan Staley
Founder and CEO
Whale Boss
312-848-7443
www.ryanstaley.io
EPISODE RESOURCES
www.startupceo.com
www.bolster.com
ABOUT THE SHOW
How do you grow like a VC-backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Andrew Gazdecki (Founder of Micro Acquire), Harpal Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.
This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets
Erik Kostelnik is the CEO of the sales and marketing platform Postal. To date, Postal has over 600 b2b customers, has raised 35 million in capital and has grown to a series B company in just 2 years. Erik has 3 successful exits under his belt including a sale to Twitter, Postal is also a product Ryan himself uses and recommends highly!
Erik talks about why Postal is an enterprise-first organisation, the insane growth companies can gain from using an offline-marketing strategy and the importance of community in the modern marketing world.
KEY TAKEAWAYS
BEST MOMENTS
“Building technology around helping companies build eCommerce and touch points is a very powerful thing”
“It’s not about the stuff, it’s about creating a love language”
“We remember the last thing sent to us; we don’t remember the last email we received”
“We’re still learning, we’re still early days”
“I encourage everyone to take a good look at product market fit and the sector you’re going after”
Do You Want The Closing Secrets That Helped Close Over $125 Million in New Business for Free?" Grab them HERE: https://www.whalesellingsystem.com/closingsecrets
Ryan Staley
Founder and CEO
Whale Boss
312-848-7443
www.ryanstaley.io
EPISODE RESOURCES
https://www.linkedin.com/in/erikkostelnik/
ABOUT THE SHOW
How do you grow like a VC-backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Andrew Gazdecki (Founder of Micro Acquire), Harpal Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.
This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets
Ryan is joined by Chris Savage, the CEO and founder of Wistia, a video platform that allows businesses to utilise the power of video. Before founding Wistia, Chris graduated from Brown university, he is also the podcast host of Talking Too Loud and a proud coffee lover!
Chris talks about how he builds his vision strategy, the impact of planning for the future before making decisions today and the current content/video market and what you should be focusing on in your business.
KEY TAKEAWAYS
BEST MOMENTS
“The most consistent, core thing we’ve done is building up that brand equity consistently with content”
“You can do all sorts of things depending on how people are consuming your content”
“If we’re going to fail, it’s going to be into obscurity”
“The audience is in control, they have unlimited competition”
“Don’t be afraid to market simple things”
Do You Want The Closing Secrets That Helped Close Over $125 Million in New Business for Free?" Grab them HERE: https://www.whalesellingsystem.com/closingsecrets
Ryan Staley
Founder and CEO
Whale Boss
312-848-7443
www.ryanstaley.io
EPISODE RESOURCES
https://wistia.com/about/chris-savage
ABOUT THE SHOW
How do you grow like a VC-backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Andrew Gazdecki (Founder of Micro Acquire), Harpal Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.
This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets
Fellow podcaster, two-time founder and CEO of Referral Rock Josh Ho joins Ryan in this episode. He talks about his background in engineering and marketing which led him to create Referral Rock, a software company that helps companies design, launch and manage referral programmes. Josh reveals the secrets to harnessing the power of referrals and how to scale a business effectively.
KEY TAKEAWAYS
BEST MOMENTS
“We’re profitable with 20 people”
“The dream of building software that makes money while you sleep”
“You had the right idea, just the wrong timing”
“Am I just incentivising the wrong behaviour?”
“We’ll investigate that brand a bit and get that baseline number so we have something to compare to”
“Our metric to focus on are engaged members”
Do You Want The Closing Secrets That Helped Close Over $125 Million in New Business for Free?" Grab them HERE: https://www.whalesellingsystem.com/closingsecrets
Ryan Staley
Founder and CEO
Whale Boss
312-848-7443
www.ryanstaley.io
EPISODE RESOURCES
https://referralrock.com/
ABOUT THE SHOW
How do you grow like a VC-backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Andrew Gazdecki (Founder of Micro Acquire), Harpal Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.
This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets
From the publisher's feed
How do you grow like a VC-backed SAAS company without taking on investors? What are the secrets that SAAS CEOs have that the rest of us don't? Do you want to create a lifestyle business, a performance business, or an empire? How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best SAAS Founders, CEOs, and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Gina Bianchini (Founder of Mighty Networks and prior Co-Founder with Marc Andreessen) and Harpaul Sambhi (Founder of Magical with a previous exit to Linkedin). This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Sales, Business growth strategy, Founder, VP of Sales, CRO, Chief Revenue Officer, Technology, Leadership, CEO, Management, Hyper-Growth.

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