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Heavy Networking

Heavy Networking

Tailscale CEO on WireGuard, Zero Trust, and Securing AI (Sponsored)

Jun 5, 2026 · 57 min · 10 segments

If you think Tailscale is just a VPN for the home lab, think again. On today’s sponsored episode Ethan and Drew are joined by Tailscale CEO Avery Pennarun. Avery explains how the company has evolved…

If you think Tailscale is just a VPN for the home lab, think again. On today’s sponsored episode Ethan and Drew are joined by Tailscale CEO Avery Pennarun. Avery explains how the company has evolved into an enterprise-grade connectivity and security platform. He also dives into Tailscale Aperture, their new AI gateway designed to bring... Read more »

If you think Tailscale is just a VPN for the home lab, think again. On today’s sponsored episode Ethan and Drew are joined by Tailscale CEO Avery Pennarun. Avery explains how the company has evolved…

Speakers: Avery PennarunGuestEthan BanksHostDrew Conry-MurrayHost

Top entities: Tailscale×124 Aperture×72 WireGuard×22 Artificial intelligence×11 IPsec×10

Greeting Avery & Past Encounters0:59 – 1:14

E

Ethan BanksHost

0:59

Avery, welcome to Heavy Networking.

E

Ethan BanksHost

1:00

It's nice to have you.

E

Ethan BanksHost

1:01

Nice to chat with you again.

E

Ethan BanksHost

1:02

I think we chatted on, was it a Cloud Gambit or a, a...

E

Ethan BanksHost

1:05

I, I can't remember which exact podcast it was, but I know we chatted in the past.

A

Avery PennarunGuest

1:08

Yeah.

E

Ethan BanksHost

1:08

And-

A

Avery PennarunGuest

1:08

I think there was a Packet Pushers.

E

Ethan BanksHost

1:10

It was a Packet Pushers-

A

Avery PennarunGuest

1:11

Is that one of-

E

Ethan BanksHost

1:11

... uh, episode of some sort, yes.

A

Avery PennarunGuest

1:13

Yeah.

E

Ethan BanksHost

1:13

Uh, okay.

TailscaleCompanySoftware-defined networking company
99%124 mentions
ApertureEntity
97%72 mentions
WireGuardSoftware ApplicationSoftware
95%22 mentions
Artificial intelligenceEntityProfessional field
93%11 mentions
IPsecEntityInternet protocol
91%10 mentions
YAMLEntityFile format
89%5 mentions
LinkedInSoftware ApplicationSocial networking service
87%6 mentions
MicrosoftCompanyTechnology company
85%7 mentions
GitHubCompanyCompany
83%6 mentions
JSONEntityFile format
81%15 mentions
Virtual private cloudEntity
79%6 mentions
AppleCompanyTechnology company
77%6 mentions
Single sign-onEntity
75%3 mentions
Microsoft Entra IDSoftware Application
74%7 mentions
Zero trust security modelEntity
72%1 mention
humorEntity
70%2 mentions
Active DirectorySoftware ApplicationSystem software
68%2 mentions
BlueskySoftware ApplicationSocial media service
66%4 mentions
AnthropicCompanyArtificial intelligence company
64%5 mentions
Bruce SchneierPersonAmerican cryptographer
62%1 mention
OpenClawSoftware ApplicationSoftware
60%10 mentions
Personal dataEntity
58%6 mentions
Large language modelEntity
56%19 mentions
Border0 Inc.CompanyCompany
54%3 mentions
Fortune 500ListRanked list
52%2 mentions
Internet of thingsEntityField of study
50%2 mentions
Secure Access Service EdgeEntity
48%1 mention
App storeEntityType of software
46%2 mentions
WebhookEntity
44%1 mention
UbuntuSoftware ApplicationSoftware
42%2 mentions
GoogleCompanyTechnology corporation
40%3 mentions
Network address translationEntity
38%2 mentions
OAuthEntityInternet protocol
36%3 mentions
OktaCompanyCompany
34%2 mentions
LinuxSoftware ApplicationSoftware
31%2 mentions
macOSSoftware ApplicationOperating system
31%2 mentions
OpenAICompanyGenerative AI company
28%2 mentions
CodexEntity
26%1 mention
HTTPEntityInternet protocol
25%2 mentions
Social SecurityEntity
23%1 mention
DropboxSoftware ApplicationSoftware
21%1 mention
GmailWebsiteWeb site
19%3 mentions
Microsoft AzureSoftware ApplicationComputer application
17%1 mention
ClaudeSoftware ApplicationSoftware
15%1 mention
Software as a serviceEntity
13%1 mention
KubernetesSoftware ApplicationSystem software
11%1 mention
Amazon Web ServicesCompanyCloud computing company
9%1 mention
YouTubeWebsiteVideo sharing company
7%1 mention
NorwayCountryCountry in Europe
5%1 mention
Secure ShellSoftware ApplicationComputer application
3%1 mention

NetworkingTechnology
Enterprise SolutionsTechnology
CybersecurityTechnology
EncryptionTechnology > Cybersecurity
Mesh NetworksTechnology > Networking
AI IntegrationTechnology > Software > Applications
AuthenticationTechnology > Identity Management
End-to-End EncryptionTechnology > Cybersecurity > Encryption
ApplicationsTechnology > Software
Identity ManagementTechnology
VPN AlternativesTechnology > Networking > Mesh Networks
TailscaleTechnology > Networking > Mesh Networks > VPN Alternatives
WireGuardTechnology > Cybersecurity > Encryption > End-to-End Encryption
ApertureTechnology > Software > Applications > AI Integration
Single Sign-OnTechnology > Identity Management > Authentication
OIDC ProvidersTechnology > Identity Management > Authentication > Single Sign-On
Policy ManagementTechnology > Enterprise Solutions
Access ControlTechnology > Enterprise Solutions > Policy Management
Network PoliciesTechnology > Enterprise Solutions > Policy Management > Access Control
Technology
SoftwareTechnology

Greeting Avery & Past Encounters0:59 – 1:14

E

Ethan BanksHost

0:59

Avery, welcome to Heavy Networking.

E

Ethan BanksHost

1:00

It's nice to have you.

E

Ethan BanksHost

1:01

Nice to chat with you again.

E

Ethan BanksHost

1:02

I think we chatted on, was it a Cloud Gambit or a, a...

E

Ethan BanksHost

1:05

I, I can't remember which exact podcast it was, but I know we chatted in the past.

A

Avery PennarunGuest

1:08

Yeah.

E

Ethan BanksHost

1:08

And-

A

Avery PennarunGuest

1:08

I think there was a Packet Pushers.

E

Ethan BanksHost

1:10

It was a Packet Pushers-

A

Avery PennarunGuest

1:11

Is that one of-

E

Ethan BanksHost

1:11

... uh, episode of some sort, yes.

A

Avery PennarunGuest

1:13

Yeah.

E

Ethan BanksHost

1:13

Uh, okay.

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