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Bootstrapped Web

Bootstrapped Webbootstrappedweb.com
Brian Casel (@casjam) and Jordan Gal (@jordangal) share their raw and real behind-the-scenes of their entrepreneur journeys. From bootstrapping software startups to raising money to selling and exiting businesses, to growing teams and the emotional rollercoaster that is startup life. It's all here in Brian and Jordan's weekly(ish) updates.

Episodes

Make it Rough

Idea hunting. Competitors. Levels. Portfolios. Rough products. Customer success. Weekly pricing. Productized services. Earthquakes. Supplements. Connect with Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's consultancy: Instrumental Products Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel...

Apr 05, 20241 hr 7 minEp. 251

Creating Content & New Product Ideas

Brian's first LinkedIn post. YouTube. Texas. Northeast. Inbound vs. outbound. New product ideas. AI. Ecommerce. Customer Success. Tapping demand. Connect with Brian: Brian's Product Studio: Instrumental Products Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Connect with Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal...

Mar 29, 20241 hr 6 minEp. 250

Ideas & Tech Stacks

Exploring new ideas via conferences. Building in Laravel vs. Rails. Training customer success. Leveraging audience as an employee vs. founder. Travel energy. Connect with Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's new consultancy: Instrumental Products Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel...

Mar 15, 202452 minEp. 249

The internet is a confusing place

SaaS trends. Product studio. Pivots. Personal energy. Business energy. Ecommerce Space. Bootstrapping. First principles. Product idea mining. Platform risk. Elementary school talent shows. Connect with Brian: Brian's Product Studio: Instrumental Products Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Connect with Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal...

Mar 08, 202455 minEp. 248

Charging for Onboarding

Launching a consultancy. Generating pipeline. Breaking limiting mindsets. Outsource vs. in-house SDRs. Paid customer onboarding. Daddy-daughter dancing. Connect with Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's new consultancy: Instrumental Products Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel...

Feb 23, 20241 hrEp. 247

New Directions

AI everywhere. Zuck's shots fired. Committing to the new direction. Customer success. "Starter for hire" consultancy concept. Skiing. Birthdays. Connect with Brian: Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Connect with Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal...

Feb 16, 202454 minEp. 246

2024 Calculus

Homepage experiments. Marketing is too expensive. Product-led growth. VC game. Bootstrapper game. Cold outreach. Over-correcting. Shingles. Vienna. Snowboarding. Connect with Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's new content: fullstackfounder.co Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel...

Feb 02, 20241 hr 2 minEp. 245

Enough Time

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. Alarms. Connect with Brian: Brian's new business: fullstackfounder.co Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Connect with Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal...

Jan 19, 202446 minEp. 244

Pipeline Energy

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 company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Connect with Brian: Brian's new business: fullstackfounder.co Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel...

Jan 12, 202435 minEp. 243

Blank Canvas

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 :) Connect with Brian and Jordan: Brian's building: fullstackfounder.co (site is coming a few days after this episode publishes!) Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal...

Jan 05, 20241 hrEp. 242

What would a young Jordan and Brian say?

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 Brian and Jordan: Brian's building: InstrumentalProducts.com Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal...

Dec 15, 202353 minEp. 241

Winning Partnerships

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 Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Brian's new thing: InstrumentalProducts.com Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel...

Dec 08, 202349 minEp. 240

Operating a Media Company

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, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Brian's new thing: InstrumentalProducts.com Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel...

Dec 01, 20231 hr 6 minEp. 239

News Diets & Work Balance

On today's episode: Our news diets and managing stress with world events New onboarding flows & outreach wins Board meeting dynamics SaaS viability in 2024 Connect with Brian and Jordan: Brian's new thing: InstrumentalProducts.com Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal...

Nov 17, 202351 minEp. 238

FOMO, Focus, and AI

On today's episode: Brian goes public with his new thing for 2024... Jordan onboards & optimizes the new sales team Discovery channels vs. relationship channels Spicy takes on AI startup land... Connect with Brian and Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Brian's new thing: InstrumentalProducts.com Brian's SaaS, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel...

Nov 10, 202355 minEp. 237

Compensation, Content, & Speed

On today's episode: Sharing our real time stories publicly & transparently Compensation for sales teams vs. product teams Developing the content muscle Self-serve & async demos and onboarding Exploring a coaching offer around product strategy Connect with Brian and Jordan: Brian's company, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal...

Nov 03, 202357 minEp. 236

Staring Reality In The Face

On today's episode: A few words on world events Brian's runway and strategic planning for 2024 Jordan's reallocating of resources and investment Brian's firing himself from sales Jordan's hiring for sales Connect with Brian and Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Brian's company, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel...

Oct 27, 202345 minEp. 235

Product Growth Levers

On today's episode: When does shipping product lead to growth? Muddy Metrics Sports, exercise, health, eating, and drinking habits Connect with Brian and Jordan: Brian's company, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal...

Sep 15, 202355 minEp. 234

Getting Outside Help

On today's episode: How we work with coaches & consultants to guide strategy & implementation UX hangover on shipped features Selling software "once" Connect with Brian and Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Brian's company, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel...

Sep 08, 20231 hr 9 minEp. 233

Context Switching

On today's episode: How we onboard and activate after a sales call Strategic pricing and show vs. don't show How to think about hiring a sales person Context switching between product work and marketing work as a solo founder. Connect with Brian and Jordan: Brian's company, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal...

Aug 25, 202358 minEp. 232

Learning to do business (over and over)

On today's episode: Building in public. Why and how? Learning sales. Process, strategy, tactics. How we learn and implement. A solo founder's dillemma Connect with Brian and Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Jordan on Threads: @jordangal Brian's company, Clarityflow Brian on Twitter: @casjam Brian on Threads: @brian.casel...

Aug 11, 202357 minEp. 231

An appropriate level of mud slinging

On today's episode: How do we think about runway and profitability? What's an appropriate level of mud throwing? Should founders spend time on personal brand? Connect with Brian and Jordan: Brian's company, Clarityflow Brian on Threads: @brian.casel Brian on Twitter: @casjam Jordan's company, Rally Jordan on Threads: @jordangal Jordan on Twitter: @jordangal...

Jul 21, 202349 minEp. 230

Launching mobile apps, sales cadence, and summer work-life.

On today's episode: Brian's back from Asia (did he stop working?) Launching the Clarityflow app on iOS and Android ( check the video ) Jordan's shifting the sales process & sequence What it takes to close larger deals Connect with Brian and Jordan: Jordan's company, Rally Jordan on Twitter: @jordangal Brian's company, Clarityflow Brian on Twitter: @casjam Yo! We're on Threads too!...

Jul 07, 202358 minEp. 229

Sales Breakthroughs & In-Person Growth Strategy

On today's episode: The value of in-person relationship building The murky side of MRR growth Transparency with our teams PGA & LIV, Apple Vision Pro and other sidetracks! Connect with Brian and Jordan: Brian's company, Clarityflow Jordan's company, Rally Brian on Twitter: @casjam Jordan on Twitter: @jordangal...

Jun 09, 20231 hr 1 minEp. 228

High status vs. low status customers

What (and when) is a SaaS "feature complete"? How do we sell and negotiate mid-market contracts? How to please customers (and which ones are worth pleasing)? ...And other tricky questions we're thinking about this week. Connect with Brian and Jordan: Brian's company, Clarityflow Jordan's company, Rally Brian on Twitter: @casjam Jordan on Twitter: @jordangal...

Jun 02, 202359 minEp. 227

Founder Shadowing

Founder shadowing (make it a thing?) chatGPT vs. hiring a writer Go to market strategy Dialing in ICP What is marketing, really? Follow Brian and Jordan: Jordan's company, Rally Brian's company, Clarityflow Jordan on Twitter Brian on Twitter...

May 19, 202350 minEp. 226

Starting Up Sooner vs. Later

Brian and Jordan give their takes on the question of whether to start up your first business earlier vs. later in life. Plus: Board meeting takeaways, MRR growth, sales demos, enterprise vs. mid-market, and BBQ smokers. Brian's business: Clarityflow (formerly ZipMessage ) Jordan's business: Rally Follow us on the Twitters: @jordangal & @casjam...

May 12, 202356 minEp. 225

Knowing what we know now...

What would we have done differently if we started Rally or Clarityflow over again? We get into that and other questions from Twitter. Keep em coming! Brian's business: Clarityflow (formerly ZipMessage ) Jordan's business: Rally Follow us on the Twitters: @jordangal & @casjam...

May 05, 202355 minEp. 224

Hangovers & Chaos

Brian's taming the chaos of inbound customer growth mixed with urgency to ship. Jordan's experimenting with 2 go-to-market strategies, one for enterprise, one with partners. Jordan's business, Rally Brian's business, Clarityflow (formerly ZipMessage )

Apr 28, 202351 minEp. 223

Raising Funding (& Pricing)

Jordan announces Rally's Series A and we unpack the whirlwind road that it took to get there. Brian launched a pricing increase, which coincided with a competitor's unexpected shut down. It's been a wild few weeks while we've been off, but we're back! Jordan's business, Rally Brian's business, Clarityflow (formerly ZipMessage )...

Apr 21, 202354 minEp. 222