Best Jayla Siciliano Podcasts (2024)

1
How to Stay Motivated in Business 11:42

2h ago11:42

11:42

Entrepreneurship is not easy, and even the most motivated entrepreneurs find themselves feeling uninspired from time to time. Instead of driving hard towards something, we find ourselves stuck in the mud, spinning our wheels and wondering how to get back into momentum. Whether you’re trying to raise money or you’re experiencing a lull between big p…

1
How to Build a Successful Startup Without Moving to Silicon Valley w/ Stefanie Monge 38:48

3d ago38:48

38:48

A couple decades ago, being a startup founder meant packing up and moving to Silicon Valley. It was the only way to easily access customers, investors and advisors. Today, you can build a business from just about anywhere without sacrificing the vital resources you need to validate your idea and get funded. As a result, many entrepreneurship commun…

1
How to Successfully Bring a Food Product to Market w/ Bruno Xavier 54:04

17d ago54:04

54:04

In the world of food entrepreneurship, having a product that tastes GOOD is only the tip of the iceberg. Going from your kitchen to a store shelf comes with a ton of considerations, steps and potential snags. The margins are razor thin. Safety and stability are critical factors that can affect the viability of the product. Getting investors, retail…

1
Revenue Mastery: How to Stay Ahead in the Short-Term Rental Game 41:56

23d ago41:56

41:56

Curious what your portfolio’s potential is? Apply for RPM at https://freewyldfoundry.com/rpm/. In this episode, Jasper Ribbers and Tom Sharkey discuss the latest updates in their podcast journey, the introduction of new team members, and the intricacies of revenue management in the short-term rental industry. They share insights on the importance o…

1
How to Find and Pitch Your Business to Strategic Partners w/ Mathew Drazic 44:37

1M ago44:37

44:37

For an early-stage entrepreneur, strategic partnerships are a critical lifeline and launchpad for growth. They allow you to amplify your mission, gain brand awareness and get input from investors and potential customers. In the world of purpose-driven consumer products, it can be hard to know where to find these collaborators, but it’s often as sim…

1
Increase your revenue with upsells with Hostfully 40:40

2M ago40:40

40:40

Curious what your portfolio’s potential is? Apply for RPM at https://freewyldfoundry.com/rpm/. In this episode of 'Get Paid for Your Pad', Jasper Ribbers discusses the latest features from Hostly with Fred Bassili and David Jacoby. They delve into the importance of upselling in the current flat market, exploring various upsell strategies and the po…

1
5 Stages of Funding: How to Close The Deal 12:29

1M ago12:29

12:29

So you’ve pitched your idea, an investor loves it and wants to give you resources to grow your business. Well done! You’ve just secured a big piece of making your vision a reality - and that’s a huge feat. Now it’s time to close the deal and actually receive the funding you’ve been seeking. Remember, once you sign the dotted line and they wire the …

1
What Angel Groups Want In a Pitch Deck w/ Jonathan Myers 40:58

2M ago40:58

40:58

When entrepreneurs send a pitch deck to angel groups, they don’t realize they have a short amount of time to grab the attention of investors. Angel groups are evaluating hundreds of pitch decks a week, so you have as little as 2 minutes to pique their interest and make them want to respond to you. There are some things entrepreneurs do that instant…

1
5 Stages of Funding: Deal Structure 12:52

2M ago12:52

12:52

Congratulations! You just found an investor who believes in you and wants to fund your business. Now comes the next hard part - structuring the deal and setting up your startup paperwork. For early stage entrepreneurs, the step can be confusing and overwhelming, but it doesn’t have to be complicated. In fact, you can get it dialed in quickly with m…

1
Before You Give Up On Your Entrepreneurial Dream, Do This w/ Shannah Game 40:01

2M ago40:01

40:01

Coming up with a brilliant business idea and sharing it with the world. Raising money and getting investors to fund said brilliant idea. Getting your first customers and crossing the profitability line. These are all stops along the entrepreneurial journey. Each of them can be hard enough to make you want to throw in the towel and go back to corpor…

1
5 Stages of Funding: How to Find and Pitch Investors 28:16

3M ago28:16

28:16

In order to get funding for our businesses, we have to find and pitch to investors. Sounds easier said than done, right? This is one of the most nerve wracking and challenging steps you’ll take, but it is worth it. If you put yourself there and talk to enough people, you will get the funding you need. Even if you’re an introvert. Even if you hate n…

1
Money Mindset: The Most Important Step in Preparing to Raise Capital w/ Jennifer Love 47:58

3M ago47:58

47:58

Before we can go out and raise money for our businesses, there are things we need to have dialed in. The idea, the numbers, our pitch and the investors we’re going after. This stuff is critical, but THE most important thing is the relationship we have with money. Trying to raise money without dialing in our money mindset is a recipe for burnout, di…

1
How Sergio doubles his STR portfolio every year 35:01

3M ago35:01

35:01

Curious what your portfolio’s potential is? Apply for RPM at https://freewyldfoundry.com/rpm/. Sergio Castaneda, founder of Jungle House, shares his journey of growing his short-term rental business from 1 or 2 buildings to 19 units. He discusses the importance of systemizing and growing the team, focusing on the owner side of the business, and tra…

1
Quit Your W2 Job or Run Your Business On the Side? How to Make the Right Choice w/ Matt Floyd & Craig Gerulski 42:31

3M ago42:31

42:31

When you know that you’re an entrepreneur at heart but you’re still working your W2 job, when do you jump ship? It’s the age old question all aspiring business owners ask themselves. On one hand, we can burn the boats and go all in on the business. You’ll have way more time to dedicate to it and you can scale faster. Or you can get the business off…

1
My Business is 3000 Miles Away From Me...Here's How I Run It w/ Avery Carl 33:41

3M ago33:41

33:41

If you’re anything like me, being an entrepreneur appeals to you because you can design the life you want and enjoy a level of freedom you can’t get from a 9-5. The problem is: a lot of us build businesses that end up creating more stress and eat away at the freedom we got into it for. Finding a business that meets your lifestyle goals is ideal. Fo…

1
Higher Revenue with Freewyld Foundry: Success Stories and Expert Advice (Part 2) 42:42

3M ago42:42

42:42

Curious what your portfolio’s potential is? Apply for RPM at https://freewyldfoundry.com/rpm/. Summary In this conversation, Jasper Ribbers and Kaye Putnam continue their discussion on revenue management. They provide examples of the impact their service has had on clients' businesses, including significant improvements in revenue. They emphasize t…

1
Wired But Tired: How to Combat Burnout As An Entrepreneur w/ Christa Orecchio 46:34

3M ago46:34

46:34

For entrepreneurs, running fast and charging hard comes with the territory. But that could be doing nothing but running us into the ground. A lot of the things we think are “normal” parts of building and running businesses are actually signs of burnout. So many of us are stuck in that “wired and tired” mode and we don’t even know that we’re well ov…

1
Higher Revenue with Freewyld Foundry: Success Stories and Expert Advice (Part 1) 38:04

4M ago38:04

38:04

Curious what your portfolio’s potential is? Apply for RPM at https://freewyldfoundry.com/rpm/. In this episode, Jasper Ribbers is interviewed by Kaye Putnam about RPM (Revenue and Pricing Management) service. They discuss the importance of revenue management for short-term rental operators and how it can significantly impact their bottom line. Jasp…

1
Familiarity and Founder Fit: The New Rules of Raising Money w/ Samuel Cummings 49:34

4M ago49:34

49:34

The playbook of raising money that people used to rely on has changed a lot over the last few years. Now that the market is more competitive and the pace of innovation is so much faster, what worked a decade ago won’t produce the same results today. Some of the best practices we were taught aren’t as entrepreneur-friendly as we think. A lot of foun…

1
The Biggest Paperwork Pitfalls and How to Avoid Them w/ Darby Wong 39:14

4M ago39:14

39:14

When you build a business, you aren’t just creating a product, you’re also setting up a legal entity. The legal side of things can be daunting (and expensive), especially when you intend to raise capital in the near or far future. Before you can even think of approaching investors, first-time founders have to make sure they have the legal ducks in …

1
Fear is the Final Frontier: How to Move Past It w/ Aiden Chase 55:08

4M ago55:08

55:08

Fear is something everyone struggles with - whether you’re trying to raise seed money or (believe it or not) a billionaire who has already had success. No wonder they call fear the final frontier! We often focus on the tangible aspects of entrepreneurship, but the mental and emotional stuff play a huge role in our success. In fact, if we don’t work…

1
5 Stages of Funding: 8 Ways to Raise Seed Money 20:10

5M ago20:10

20:10

In the journey of starting a company, realizing that you need to raise money is par for the course. Maybe you need to test your product’s viability, increase your stock, or grow your team…these steps require funding. Venture capital is the path many entrepreneurs take, but there are actually 7 other ways to get the funding you need. Each method has…

1
To Raise Money or Not to Raise Money? How to Make the Right Decision w/ Ashley Chang 31:38

5M ago31:38

31:38

Raising money through investors is the default for growing a company, but it might not be the right move for everyone. Taking the VC route is like walking through a one-way door - once you make that decision it sets you on a specific trajectory. That’s why more entrepreneurs are being thoughtful about the decision, and even opting out of raising mo…

1
Shark Tank Winner Jayla Siciliano Pivots Into Luxury STRs 47:53

5M ago47:53

47:53

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download Jayla Siciliano, former Shark Tank entrepreneur, shares her experience on the show and the challenges she faced in building her wine company. She discusses the im…

1
How we increased RevPAR 30% for Del Carmen Hospitality 51:38

5M ago51:38

51:38

Apply for our revenue management service at https://freewyldfoundry.com/rpm/. Jairo Osorno, founder of Del Carmen Hospitality, shares his journey in the short rental business, from starting with a single unit to managing 51 listings. He discusses the challenges of the master leasing model, the impact of COVID-19, and the importance of revenue manag…

1
Every STR operator has to focus on Revenue Management in 2024 56:46

5M ago56:46

56:46

Apply for our revenue management service at https://freewyldfoundry.com/rpm/. In this conversation, Eric Moeller and Jasper Ribbers discuss the recent developments and updates related to Freewyld, including real estate, hospitality, revenue management, and the launch of Freewyld Foundry. They also delve into the importance of guest experience, bran…

1
5 Stages of Funding: How to Make Your Mindset Unshakeable 34:44

5M ago34:44

34:44

The process of raising money is as much a mental one as it is a financial one. Before we start finding and pitching to investors or even structuring our deals, there’s a step we can’t skip, working on our mindset. There’s no sugar-coating it - getting funded is one of the hardest things you’ll do. You’ll get told your idea doesn’t doesn’t work. You…

1
Business is Equal Parts Art and Science: How to Trust Your Gut w/ Diana Wilson 51:34

5M ago51:34

51:34

The process of building a company, getting funded and bringing a product to market isn’t just data-driven. It’s gut-driven too. The numbers matter, but when you’re building a product without market acceptance, you have to trust your intuition and persevere when you’re told it won’t work. In many ways, taking an entrepreneurial risk is a lot like ta…

1
Why I Walked Away From The Company Mark Cuban Invested In 43:16

6M ago43:16

43:16

Building a company, going on Shark Tank, raising $1 million dollars and working with Mark Cuban. Sounds like an entrepreneur’s dream, right? Well, that’s what I thought, until I walked away from it. It was the hardest decision I’ve ever made, but also the best one. When you build your own company, it becomes an extension of you, so stepping away is…

1
Everything You Need to Prep For An Investor Meeting w/ Keir Dillon 53:10

6M ago53:10

53:10

In the path to getting funding for your idea, meeting with investors is the most important checkpoint. You only have one shot at a first impression, so the more dialed in your presentation is, the more successful you’ll be. From pitch decks to financials, there’s a ton of work that goes into preparing for that face-to-face with a potential funding …

1
Mitigate Risk and Keep Your STR Properties Safe 40:55

6M ago40:55

40:55

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download Vincent Niemeth, a safety expert in the short-term rental field, shares his insights on safety and liability in the industry. He emphasizes the importance of gues…

1
Make “Boring” Cool: The Secret to Disrupting A Tired Category w/Josh Walker 46:59

6M ago46:59

46:59

The best products disrupt tired categories and breathe new life into done-to-death ideas, but is it still possible? Every year, there are fewer categories to disrupt, especially in clothing-based niches. How can you compete when people can easily buy knock-offs, dupes and cheap goods all over the internet? By going premium, identifying an emerging …

1
Investing in Turnkey Real Estate Properties 33:45

6M ago33:45

33:45

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download Zach Leimaster, founder and CEO of Rent to Retirement, discusses how he helps people retire early with turnkey rentals. He explains that turnkey rentals involve i…

1
Nick's Airbnb Nightmare story 36:47

6M ago36:47

36:47

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download Nick Libertin shares his experience of his short-term rental property burning down and the challenges he faced with insurance coverage. He emphasizes the importan…

1
My Shark Tank Story (and How It Almost Didn't Happen) 27:17

6M ago27:17

27:17

Years later, people still ask about this story. So here it is. Pitching to a group of influential investors is a nerve-wracking experience, and that’s even before you have to do it on national TV! It’s not just a business presentation - you have to be entertaining, compelling, relatable and likable. I found that out when I appeared on Shark Tank. A…

1
Underwrite STR Properties with STR Insights 32:14

6M ago32:14

32:14

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download Kenny Bedwell, founder and CEO of SDR Insights, shares his expertise on analyzing short-term rental properties. He emphasizes the importance of understanding the …

1
Storytelling Is The Secret to Successful Seed Funding w/Dan Negroni 51:36

7M ago51:36

51:36

The world of seed funding runs on two currencies - money and connection. Investors aren’t just paying attention to the financials, they are looking for a compelling story that makes them connect with us and then want to get on board. Crafting our story is a step we can’t skip in the early stages of our businesses. The more clarity we have on it, th…

1
How to develop a revenue management mindset 28:09

7M ago28:09

28:09

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download In this episode, Jasper Ribbers interviews Mike Savage, the founder of Synergy Stays, about revenue management in the short-term rental industry. They discuss the…

1
Mid Term Rental Strategies 31:49

7M ago31:49

31:49

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download Ziona McIntyre, author of '30-Day Stay: A Real Estate Investor's Guide to Mastering the Medium-Term Rental', discusses strategies for finding and managing mid-ter…

1
Seed Money- What Blew My Mind About Early-Stage Funding 9:53

7M ago9:53

9:53

Early-stage fundraising may be a stressful stage in business, but it can also be the most invigorating and exciting time. The determination, drive, conviction, and guts it takes to get seed money is a powerful life force. It’s not just an opportunity to get the resources we need. It’s a chance for investors to access your awesomeness, and absorb th…

1
Seed Money Trailer 1:43

7M ago1:43

1:43

Seed Money is where everyday people learn how to raise capital and get the funding you need to FINALLY turn your amazing idea into reality! Whatever your idea is.. product app real estate deal …or maybe you want to build or expand your small business… if you’re struggling to get people to believe in your vision and you don’t need a billion dollar d…

1
Guest marketing with Stay-Fi 30:31

7M ago30:31

30:31

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download In this episode, Jasper Ribbers interviews Arthur Colker, the founder of Stay-fi, a guest Wi-Fi marketing tool. They discuss how short-term rental operators can c…

1
The state of the STR industry with Rent Responsibly 40:11

7M ago40:11

40:11

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download In this episode, Jasper Ribbers interviews Dave Krauss, the co-founder of Rent Responsibly, an organization that supports the short-term rental industry. They dis…

1
Live Let Thrive with Steven Suarez 1:09:46

8M ago1:09:46

1:09:46

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download Hosted on Acast. See acast.com/privacy for more information.

1
Revenue Management Strategies 36:14

8M ago36:14

36:14

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download In this episode, Jasper Ribbers interviews Jordan Locke, the founder of RevParty Consulting, about revenue management strategies for short-term rentals. They disc…

1
Sailing around the world funded by property investing 34:07

8M ago34:07

34:07

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download In this episode, Jasper Ribbers interviews Jordan Locke, the founder of RevParty Consulting, about revenue management strategies for short-term rentals. They disc…

1
How Steven went from near bankruptcy to building a thriving STR business 42:42

9M ago42:42

42:42

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download In this episode, Jasper Ribbers interviews Steven Suarez, the founder of Argest Rentals, about his experiences in property management and the challenges he faced …

1
Experiential design is where the money is at on Airbnb 37:14

9M ago37:14

37:14

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download In today's episode of Get Paid for Your Pad, I had the pleasure to talk to Heather Loduca & Erin Donnelly, the founders of Pink Wall Designs, straight out of Cana…

1
How a near death experience inspired two brothers to go all-in on STRs 44:00

9M ago44:00

44:00

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download In today's insightful episode of "Get Paid for Your Pad," I had the distinct pleasure of discussing the evolving landscape of the short-term rental industry with …

1
Curate local experiences for your guests with Mount 35:04

11M ago35:04

35:04

>>> Watch our free Revenue Management training at https://www.getpaidforyourpad.com/cfm-replay >>> FREE E-Book: 5 Most Common Airbnb Revenue Management Mistakes >>> Click here to download In this episode of "Get Paid for Your Pad," I, Jasper Ribbers, engage in an insightful conversation with Madison Rivkin, founder of Mount. We delve into the conce…

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Jayla Siciliano Podcasts

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