Best Jayla Siciliano Podcasts (2024)

1
The Great Stalemate: Buyers, Sellers, and Interest Rates in 2024 with Brenna Carles 32:21

5h ago32:21

32:21

In this episode of the Short Term Show, Avery and Brenna Carles discuss the current mortgage rates landscape with a focus on investment and second home loans. They go over what factors influence interest rates, how the media impacts interest rates, the possibility of future rate cuts and more. How to connect with Brenna: @the.mortgage.shop @brenna.…

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

1h 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
Lindsey Iskierka's Journey Investing in Southern California and Beyond 50:56

2h ago50:56

50:56

In this episode of the Short-Term Show, Lindsey Iskerka shares her journey from personal trainer to successful real estate investor in California. Lindsey discusses her initial skepticism about real estate as a wealth-building strategy, her entry into the industry through a mentorship program, and her eventual success in house hacking, out of state…

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

4h 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

21h 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
How Kassidy Warren Scaled Up From Van Life to Boutique Hotels 36:49

6d ago36:49

36:49

This week, Avery interviews Kassidy Warren, who shares his journey of leaving the corporate world to pursue full-time short-term rentals and van life. Kassidy discusses his background growing up frugal, his transition from an engineering career in the corporate world, to his burnout and desire for a change in direction. Kassidy detailed his initial…

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

7d 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
Defending the STR Tax Loophole: Ryan Bakke's Success Story 27:43

23d ago27:43

27:43

In this episode of the Short Term Show, CPA Ryan Bakey shares his experience defending and winning an audit on the STR tax loophole. Ryan emphasized the importance of having a CPA who specializes in real estate and understands the intricacies of the tax laws related to short-term rentals. They also discussed how critical it is to maintain meticulou…

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

24d 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
Scaling Smart: Financing and Managing Multiple STRs with Jen Dickson 33:49

20d ago33:49

33:49

In this episode, Avery had the pleasure of speaking with Jen Dickson, a seasoned short-term rental investor who has successfully navigated multiple markets. Jen detailed their strategic approach to selecting markets, emphasizing the importance of choosing locations they personally enjoy and frequent. They also delved into the financial aspects of t…

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

1M 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

1M 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
Adam Czajkowski's Journey From MLB Scout to Real Estate Investor 32:36

27d ago32:36

32:36

In this episode of the Short Term Show, Avery interviews Adam Czajkowski. Adam shares his unconventional journey into real estate, starting from a background in baseball to working for the New York Yankees, and eventually transitioning to sales to gain back time and financial stability. They delved into the challenges of finding deals, especially i…

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

28d 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
Navigating Securities Law and Syndications with Bethany LaFlam 41:24

1M ago41:24

41:24

In this episode, Avery had the pleasure of speaking with Bethany LaFlam, the managing partner of Premier Law Group. Bethany shared her extensive knowledge as a securities lawyer, explaining the intricacies of syndications and joint ventures, particularly in the context of short-term rentals. She highlighted the importance of compliance with SEC reg…

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

1M 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
Creating Unique Guest Experiences in Remote Locations with Lauren Cecil 49:39

1M ago49:39

49:39

This week Avery is joined by Lauren Cecil, an innovative entrepreneur who has successfully transformed her property in West Texas into a multi-faceted business. She shares her journey of transforming her inherited property into a thriving business that includes a campground, a luxury short-term rental, and a Jeep rental service. She talks about the…

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

2M 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
Jayla Siciliano's Path from Shark Tank to Real Estate 34:45

2M ago34:45

34:45

This week Avery is joined by Jayla Siciliano, CEO of Atlas Vacations and host of the Seed Money podcast, who shares her experience appearing on Shark Tank in season five. She describes the behind the scenes of Shark Tank and the lasting impact of the exposure gained from the show. Jayla also shared the story of how her foray into real estate began …

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

2M 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
Using a Design-Centric Approach to Maximize Profits with Ishita & Harshad Lalan 35:54

2M ago35:54

35:54

In this episode, host Avery Carl interviews Ishita and Harshad Lalan, the founders and owners of Ishita Interiors. The couple shares their journey into the world of STRs as investors and how their background in design and engineering has shaped their success in the industry. Ishita and Harshad discuss their unique approach to STR design, focusing o…

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

2M 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
Maximizing Your Property's Potential with Neighbor CEO Joseph Woodbury 26:02

2M ago26:02

26:02

On this episode, Avery is joined by Neighbor CEO and founder Joseph Woodbury. Joseph shares how Neighbor provides a unique opportunity to maximize income from short term and long term rentals. Joseph also addresses common concerns, such as the types of items allowed and the security measures in place to ensure high-quality renters. He emphasizes th…

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

2M 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

2M 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

3M 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
Mastering Real Estate Investments While Creating Legendary Family Lives with Jim Sheils 34:53

2M ago34:53

34:53

This week Avery is joined by Jim Sheils, real estate investor who specializes in the build-to-rent model. They discuss the advantages of Build-to-Rent, emphasizing its efficiency in reducing maintenance costs and increasing tenant retention compared to older properties. Jim highlights the importance of starting small, and the necessity of understan…

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

3M 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

3M 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
AJ Osborne on Overcoming Adversity and Building a Self-Storage Empire 55:40

3M ago55:40

55:40

In this episode, Avery sits down with AJ Osborne, a self-storage investing mogul and the founder of Cedar Creek Capital. AJ shared his incredible journey from insurance sales to becoming a leading figure in the self-storage industry, and how this asset class played a crucial role during a life-altering personal crisis. AJ emphasizes the concept of …

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

3M 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
Diving Deep into House Hacking with Craig Curelop 27:41

3M ago27:41

27:41

In this episode, Avery is joined by Craig Curelop to talk about the house hacking strategy and how it can change the tragectory of your life. They discuss the different approaches to househacking, how fluctuating interest rates have impacted house hacking, the most ideal markets for house hacking and more. How to connect with Craig: https://www.the…

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

3M 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
Bryan Cataldi Returns: The Completion of a Multi Cabin Rehab Project 34:33

3M ago34:33

34:33

In this episode, Avery is joined by guest Bryan Cataldi for a follow-up on his journey of rehabbing a seven-cabin development in the Smokey Mountains. Brian shares his experiences from the project, highlighting the hard work and dedication required in the short term rental business. They discuss some impressive rental stats, his rehabbing strategy …

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

3M 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

4M 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
The Six-Minute Money Machine: Unlocking STR Success with Philip Kennard 36:40

4M ago36:40

36:40

In this episode, Avery sits down with Philip Kennard, the founder of FutureStay, a property management operating system designed for the modern rentalpreneur. Philip shares his journey from a tech-savvy teenager to a successful entrepreneur who stumbled into the short-term rental industry by necessity. He emphasizes the importance of building the r…

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

4M 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

4M 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

4M 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
Maximizing Efficiency and Guest Satisfaction Using Smart Property Technology with Angel Piontek 27:14

4M ago27:14

27:14

In this episode, Avery interviews Angel Piontek, the head of marketing at Point Central, a smart home technology company. They discuss various smart devices for short-term rentals, including smart locks, smart thermostats, and a few you might not have considered before, such as water sensors, door and window sensors, and smart noise monitors. Angel…

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

4M 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

4M 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
Mastering the Art of Wholesaling Real Estate with Jamil Damji 45:41

4M ago45:41

45:41

In this week's episode, Jamil Damji joins Avery to share his journey of self-teaching in real estate wholesaling for over 20 years and how it has shaped his unique approach to the business. They discuss the importance of ethics in real estate as well as the importance of relationships. Jamil shares his extensive experience in real estate wholesalin…

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

4M 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

4M 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

4M 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
Dissecting AirDNA's Latest Updates with Jamie Lane 57:44

4M ago57:44

57:44

In this episode, Jamie Lane from AirDNA joins Avery to discuss the recent changes in AirDNA's interface and pricing. Jamie shares insights on how AirDNA tracks short-term rental data worldwide, providing insights on revenue, occupancy, amenities, and more. He highlights the significance of local expertise, as well as the importance of understanding…

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

4M 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

4M 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…

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Jayla Siciliano Podcasts

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