Rachel, pt. II, on "Facebook official" and exes

The Undesirables

#Tech #Society #Conversations #Comedy #Tucker Winstanley, Tom Ella #Tom Ella #Tucker Winstanley

34:07

In this insightful episode of The Innovators & Investors Podcast, host Kristian Marquez sits down with Jay Crone, Managing Director and Venture Capitalist at Deloitte Ventures, to explore the firm’s strategic approach to corporate venture capital. Jay shares Deloitte Ventures’ investment thesis, focusing on supporting innovative Canadian startups at Series A and B stages across key sectors like cybersecurity, climate tech, fintech, future of work, health tech, and AI. Listeners will gain an inside look at how Deloitte leverages its vast network of 1,500 partners and 15,000 employees to source deals and add value beyond capital by helping startups navigate Deloitte’s complex ecosystem and access enterprise clients. Jay also discusses his diverse career journey—from government and investment banking to entrepreneurship and corporate VC—and how those experiences shape his investment philosophy. The episode delves into Deloitte’s due diligence process, the importance of founder relationships, and the firm’s strategic role as a co-investor. Jay highlights emerging trends, particularly the promise of vertical AI tailored to industry-specific needs, and shares his bullish outlook on fintech innovations like stablecoins and cross-border payments. He offers candid advice for entrepreneurs on risk-taking and aligning business vision with funding goals. This episode is a must-listen for founders, investors, and anyone interested in the evolving landscape of corporate venture capital and innovation in Canada. Learn more about Jay's work at https://www.deloitte.com/ca/en/services/program/ventures.html Connect with Jay on LinkedIn at https://www.linkedin.com/in/jaycrone/ Think you'd be a great guest on the show? Apply at https://finstratmgmt.com/innovators-investors-podcast/ Want to learn more about Kristian Marquez's work? Check out his website at https://finstratmgmt.com…

6 years ago 1:07:14

MP3•Episode home

While Rachel and Tucker re-litigate their breakup, Tom gets sad over his own.

Along the way, they answer some important questions like does Piggly Wiggly still exist and how sensually do you lick someone's elbow on the first date?

If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins.

Thanks to Rachel for taking the time and making the trip to be on this podcast TWICE this year. What a hero. Catch her humor and her face on Instagram @unfortunate_selfies and watch her and Tucker yell at each other on Twitter by following her @anti_socialite_

Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com.

40 episodes

Rachel, pt. II, on "Facebook official" and exes

The Undesirables

published 6 years ago

MP3•Episode home

While Rachel and Tucker re-litigate their breakup, Tom gets sad over his own.

Along the way, they answer some important questions like does Piggly Wiggly still exist and how sensually do you lick someone's elbow on the first date?

Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com.

40 episodes

#Tech #Society #Conversations #Comedy #Tucker Winstanley, Tom Ella #Tom Ella #Tucker Winstanley

All episodes

1
Closure: The Season Finale 1:23:42

6 years ago1:23:42

1:23:42

When some ghosts from Tom's past return in dramatic fashion, the boys realize they have no choice but to resurrect senior relationship expert correspondent Kait Emery to inject once again some much-needed wisdom into their well-intentioned mania and neuroses. [NOTE: For the full context of these stories, please listen to episodes 13-15 of season two.] It's been a long season, y'all. We laughed. We cried. We contracted (and importantly, cured ) chlamydia. But things are coming to a stop here for a little bit while we regain our sanity and maybe kiss a person or two off mic for a bit. Thank you all for continuing to listen as we publicize our ignorance. Thank you to our guests, Dr. Deanna Richards, Rachel Kidd, Will Gleason, Laura and Dylan Petro , Lindsey Metselaar, Ben Goodman, Peter A. , Tori Piskin , Kait Emery, Dr. Maggie Dancel, B & L , James Petrine, Pete and Josh , and then Kait Emery again. See you again soon! If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
"I have chlamydia" 48:15

6 years ago48:15

48:15

We all knew it would come to this. If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
The Sexual Fantasies Quiz 52:12

6 years ago52:12

52:12

Tom, Tucker and official Undesirables senior gay correspondent James dive into a sexual fantasies quiz from Tell Me What You Want , a book that takes a fascinating, comprehensive look at the complexities of Americans' sexual fantasies. Tell us a little about yourself and we can guess your sexual fantasies using this 15-question quiz. Are you organized? Democrat or Republican? Religious? Ohhh wow, you're into some stuff . Listen as we each take the quiz ourselves and learn the horrifying origins of our kinks. If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
Reporting LIVE from Tucker's bedroom 1:36

6 years ago1:36

1:36

With Tucker out on assignment, Tom drops the hard news: There's only three episodes left in the season. "Only three episodes left in the season?!" Oh, you read that right. But keep in mind, these are gonna be top quality, primo, prime cut episodes of The Undesirables. You're gonna leave this season feeling so satisfied with how it all played out. If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
Pete and Josh, hosts of Poe Boys, a Star Wars podcast 24:45

6 years ago24:45

24:45

Tom, not able to take the idea of asking Tucker another single question about his dating life, decides to hop on a train out of the city to catch up with his old friends and hosts of the Poe Boys podcast , Pete and Josh. Together, they know nearly everything about Star Wars and absolutely nothing about how to successfully navigate the world of modern dating. There's truly no group of less qualified people for a dating podcast and yet here we are, telling you how long you should wait to tell someone you're interested in about your nerdy passions, giving a look into what it's like to date as a catholic, and finally asking what the hell coffee meets bagel is all about. Don't forget to follow Poe Boys on Twitter if you're even slightly interested in whats happening in the world of Star Wars. And if you're into it, leave a review on iTunes ! If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
Kissin' dudes, dating profile review, and shout outs 39:30

6 years ago39:30

39:30

Tucker and Tom decide to let their natural charisma take over to talk about something other than kissin' ladies for a change... and end up talking about kissin' dudes. They talk about the motivation behind casual smooching, the difference between finding someone attractive and being attracted to them, and try to leave a little hope open for all the fans shipping a Tucker-Tom romance story. Then phones get traded and dating profiles get a hard review. Pictures scrutinized and answers shredded. Finally, by popular demand, Tom revives closing segment Shout Outs to give props to some particularly good profiles on Hinge. If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
James, senior gay correspondent, on Grindr, hookup culture, and tongue 49:50

6 years ago49:50

49:50

No one has more dirt on Tucker and Tom than James. No one. He's known them for decades, lived with them for a full year, and liked them for weeks. Official Undesirables senior gay correspondent James goes deep on Grindr and hookup culture, while Tucker goes on his first ever Bounce date, and Tom decides now is the time to ask for the group's most embarrassing sex stories, which backfires tremendously. If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
Read receipts, dating attrition, and tangents 36:11

6 years ago36:11

36:11

After so many out-of-order or months-delayed episodes, Tucker and Tom take a quick squat and chat about what going on in their dating lives right now. Tom's soliciting teens for "journalism," Tucker's taking a break for "sanity," and they're both impossible to keep on topic. Also, people, this is the beginning of the end... of season two. We're in the home stretch now. We've got probably four or five (maybe six, we'll see) episodes left before we call it a wrap, and you're not going to want to miss a single one. If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins. Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com.…

1
B & L, the anonymous hosts of Not Your Girlfriend's Podcast 1:04:19

6 years ago1:04:19

1:04:19

Imagine Tucker and Tom unleashed. No more of this weak "let's rein it back to protect our friends and loved ones." That's what it's like for B and L, the anonymous hosts of Not Your Girlfriend's Podcast. They can get real, and they do here as the group discusses first dates, commitment, getting over exes and how important are orgasms to sex. If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins. Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com.…

1
Dr. Maggie Dancel, psychologist and sex therapist 46:42

6 years ago46:42

46:42

Finally seeking outside help, Tucker and Tom bring in Dr. Maggie Dancel, a clinical psychologist specializing in sex, to answer burning questions like: What is "too much masturbation"? What does a sex dungeon actually look (and smell) like? How quietly can you say the word "poop"? Then, buckle up because Tom returns the favor by reading from his extensive notes taken at a bonafide sex class called How to Please a Woman (Squirting Tutorial Included). Yes, really. If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
A Song of Ignorance and Identity 59:10

6 years ago59:10

59:10

When Tom downloads a new dating app called Feeld and discovers a whole new world of gender identity and sexual orientation, he and Tucker decide it's high time to confront their towering ignorance. What's the difference between demi- and pansexual? What qualifies as skoliosexual? And what could "Two-Spirit" possibly mean, anyway? Note: We have a lot of laughs along the way, but this is a genuine attempt by two straight white male idiots to learn. If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
Tom's Jenny debacle, pt. III, an extreme ghosting 21:35

6 years ago21:35

21:35

In the last episode Jenny, Tom's friend turned romantic interest, seemingly dropped off the face of the planet. A few days later, Tom finally gets a response. Tune in to find out what happened to Jenny, and if a friendship can be salvaged after a romantic fallout. If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
Kait Emery, pt. II, on Tom's great Jenny debacle 51:02

6 years ago51:02

51:02

In the second half of our chat with Kait, Tom tells the story his rom-com gone wrong while Kait weighs in on topics like how to take your own wants into consideration when defining the relationship, the boundaries of ghosting, and the normalcy of post-date paranoia. Don't forget to check out Tom's new article for Tinder: The Surefire Sign She Likes You . If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
Kait Emery, senior relationship expert correspondent 31:19

6 years ago31:19

31:19

In the first of three gripping installments, Tucker brings in official Undesirables senior relationship expert correspondent Kait Emery to dissect and diagnose Tom's latest lady problems. This first case involves a particularly complicated ghosting that leaves both Tucker and Tom more frazzled than usual. Can Kait crack the case? Don't forget to check out Tom's new article for Tinder: The Surefire Sign She Likes You . If you like what you hear, please leave a five-star review on iTunes; it really does make a difference! Give us a shout on social media, share us with a friend, like us on Facebook, and follow us on Twitter or Instagram: @undesirablespod @mrthomasella @tuckerwins . Photography by the talented and patient Sam Liebeskind who you can find at samliebe.com .…

1
Tori Piskin, pt. II, on texting, chivalry and Tinder disasters 47:32

6 years ago47:32