Bootstrapped Web

Bootstrapped Web


Latest Episodes

2024 Calculus
February 02, 2024

Homepage experiments. Marketing is too expensive. Product-led growth. VC game. Bootstrapper game. Cold outreach. Over-correcting. Shingles. Vienna. Snowboarding.Connect with Jordan:Jorda

Enough Time
January 19, 2024

Customer Success. Offers product.Consulting aint so bad. Hiring a video editor. Redefining success. Not enough time. Ski trips with kids. Ski trips with adults. Selling before launching. Alar

Pipeline Energy
January 12, 2024

Energizing the pipeline, energizing customer success, shipping a marketing site, unrealistic time estimations, getting snowed in, too much coffee (or not enough?)...Connect with Jordan:Jordan's

Blank Canvas
January 05, 2024

New Year, new start, a blank canvas... Working more (or less). Clarityflow Commerce. New brand name. YouTube. Growing pipeline. Selling a product two ways. Runway pressure. Just another year :

What would a young Jordan and Brian say?
December 15, 2023

In our final show of 2023, we're going deep... What would our younger selves think? What were our biggest milestones to date? Hardest challenges? What's our favorite "cheat code"?Connect with Br

Winning Partnerships
December 08, 2023

Creator businesses. Self-serve demos. Partnership Gold. Stair-stepping. Sales process. Economy and SaaS. YouTube. Marketing in 2024. Audience. What else? We'll see...Connect with Brian and

Operating a Media Company
December 01, 2023

Black Friday fun. Cold email. Sales teams. Product market fit. Website redesign. Media company operations. Audience funnels.Connect with Brian and Jordan:Jordan's company,RallyJordan on Twitter:

News Diets & Work Balance
November 17, 2023

On today's episode:Our news diets and managing stress with world eventsNew onboarding flows & outreach winsBoard meeting dynamicsSaaS viability in 2024Connect with Brian and Jordan:Brian's ne

FOMO, Focus, and AI
November 10, 2023

On today's episode:Brian goes public with his new thing for 2024...Jordan onboards & optimizes the new sales teamDiscovery channels vs. relationship channelsSpicy takes on AI startup land...Con

Compensation, Content, & Speed
November 03, 2023

On today's episode:Sharing our real time stories publicly & transparentlyCompensation for sales teams vs. product teamsDeveloping the content muscleSelf-serve & async demos and onboardingExplori