Bootstrapped Web
Episodes
2025 recap & 2026 outlook
17 Dec 2025
Contributed by Lukas
Hey! Back in your feed for our bi-annual updates! It's December 2025 and that means it's time for our year-end recap and year-ahead outlook.What J...
2025 Mid-Year Update
21 Aug 2025
Contributed by Lukas
We're back for a mid-year update!The last time we were on the mics together it was January 2025. So what's the outlook 8 months into the year?What w...
Our final episode (for now)
09 Jan 2025
Contributed by Lukas
It's true. We're calling this a final episode—for now—but don't unsubscribe! We promise to pop into the feed every few months to catch up :) B...
Year-end takeaways & goals
13 Dec 2024
Contributed by Lukas
2024 look-back and takeaways. 2025 goals. Let's go! Connect with Brian: Follow Brian on Bluesky / Twitter Brian's products: Building! Instru...
Bluesky.
06 Dec 2024
Contributed by Lukas
Bluesky takes. Activation funnels. Retention. Delegating. Demo videos. Video marketing. Sick vacations. Connect with Jordan: Follow Jorda...
Building out of a job
08 Nov 2024
Contributed by Lukas
Putting in more hours to put in less. Building systems for delivering software. Deploying demo video(s). Listening to customers. Using a busin...
"Thank you for solving my problem."
01 Nov 2024
Contributed by Lukas
Bluesky is having a moment. Halloween. Customers telling us their problems are solved. Essential onboarding. Calm before the (hiring) storm. P...
Probably fine
25 Oct 2024
Contributed by Lukas
Join us in the (free) Bootstrapped Web community on Ripple.fm Today: Political noise. Removing features. Positioning. Products for developers. ...
Funnels & Moonshots
18 Oct 2024
Contributed by Lukas
Hey we didn't talk about WordPress this week! But we did talk about Elon... Also: Brian's working on a components product (instrumental.dev), Jord...
Products For Builders
11 Oct 2024
Contributed by Lukas
Join us in the (free) Bootstrapped Web community on Ripple.fm Today: Brian's new product (Instrumental.dev). Comparing the open-source leadership s...
Pressing Questions
27 Sep 2024
Contributed by Lukas
Brian and Jordan's expert (lol) takes on WordPress-land. Car shopping. Netflix rec's. Funnel tracking. Customer observations. Over-building....
Onboarding Funnels
20 Sep 2024
Contributed by Lukas
Join us in the (free) Bootstrapped Web community on Ripple.fm Today: Optimizing our onboarding funnels. Calls to action. Lead ads. ARPU. API ...
What Customers Want
13 Sep 2024
Contributed by Lukas
Q4 energy. Signup funnels. Self-serve vs. not. Building assets vs. building cashflow. Membership business models.  Join our free community ...
Why is SaaS hard?
30 Aug 2024
Contributed by Lukas
Join us in the (free) Bootstrapped Web community on Ripple.fm Today: Why makes SaaS more difficult than other business models? Rosie first customer...
If we bootstrapped
22 Aug 2024
Contributed by Lukas
Today on Bootstrapped Web: What if we bootstrapped? Funnel projects. Pricing experiments. Software speed. Tech-enabled services. Listener co...
Funnels & Websites
16 Aug 2024
Contributed by Lukas
Connect with Brian, Jordan and fellow listeners in the Bootstrapped Web community on Ripple.fm Today: Asking the hard-hitting questions like... Cocon...
Networks & Audiences
09 Aug 2024
Contributed by Lukas
Ripple.fm is live and open. Rosie is live for self serve signups. Niche social networking. Advertising using video. Cold outreach playbooks. ...
Pricing Experiments
02 Aug 2024
Contributed by Lukas
Brian launches built and launched something new. 2 things actually. Jordan changes pricing strategy for Rosie. Brian also changes pricing strate...
Era of Trying Stuff
18 Jul 2024
Contributed by Lukas
Yet another new product announcement from Brian. Jordan launches to first customers. The era of hacking on new ideas. Summer speed ups. Professi...
What's Next?
12 Jul 2024
Contributed by Lukas
Brian's next product announcement. Marketing first. Small bets. Private podcasting. AI product development speed. Summer vacations. Connect ...
The Morning After
28 Jun 2024
Contributed by Lukas
US Presidential debate analysis. America. Launch week. First customers. Perfect storm for a new product idea. Questioning assumptions. See...
Dialing In
21 Jun 2024
Contributed by Lukas
Tailor-Made UI. Knowing your customer. Launch-week learnings. Sales calls. Cold outreach. Margin & space. Date night hangovers. Summ...
Hey, Rosie
14 Jun 2024
Contributed by Lukas
Launching heyrosie.com. First demos. Twitter feeds. Productized consulting. Homepage rewrite. Summer camp. Concerts. Connect with Jordan: ...
Prompt Engineering
07 Jun 2024
Contributed by Lukas
Launch week. AI demos. Prompt engineering. Help docs. Product marketing. New feature prep. B2B vs. B2C strategies. Coastal living. Mai...
Build in public
31 May 2024
Contributed by Lukas
Troubleshooting back pain. "Early access" vs. "Sign up". Build (or brag) in public. Bootstrapping via consulting. Starter app templates. The...
Launch and learn
24 May 2024
Contributed by Lukas
Shady domain brokers. Cooling off on product ideas. Pricing questions. High vs. low volume funnels. Launch and learn. Conflicting realities....
AI Products
17 May 2024
Contributed by Lukas
GPT-4o. Sleepless nights. Product idea excitement. Self-serve funnels. Keeping calm before the storm. Selling to small business. Knicks in...
Product Hunting
10 May 2024
Contributed by Lukas
No, we're not talking about Product Hunt (the website) today. This one's about:Hunting for new product ideas. Categories in AI. Finding a partne...
Startup Names
03 May 2024
Contributed by Lukas
Choosing a name. YouTube experiments. SEO. Reaching a foreign industry. Branding exercise. The New York Knicks. Connect with Jordan: Jordan's company...
Entrepreneurial Seasons
26 Apr 2024
Contributed by Lukas
Protyping with AI. Burnout aftermath. Validation theories that need retiring. Go-to-market. MVP speed. SaaS UI components as a service. Ki...
Not Selling to SaaS
19 Apr 2024
Contributed by Lukas
Email for SaaS. Selling to Main Street. AI in the real world. Offloading customer support. UI/UX consultancy pricing. YouTube experimentatio...
Sell to SaaS?
11 Apr 2024
Contributed by Lukas
Exploring products that sell to SaaS. Flights. Credit card points. Passover. Elections. Twitter. Validation. No-kids vacations. Connect ...
Make it Rough
05 Apr 2024
Contributed by Lukas
Idea hunting. Competitors. Levels. Portfolios.  Rough products. Customer success. Weekly pricing. Productized services. Earthquakes. ...
Creating Content & New Product Ideas
29 Mar 2024
Contributed by Lukas
Brian's first LinkedIn post. YouTube. Texas. Northeast. Inbound vs. outbound. New product ideas. AI. Ecommerce. Customer Success. Ta...
Ideas & Tech Stacks
15 Mar 2024
Contributed by Lukas
Exploring new ideas via conferences. Building in Laravel vs. Rails. Training customer success. Leveraging audience as an employee vs. founder. ...
The internet is a confusing place
08 Mar 2024
Contributed by Lukas
SaaS trends. Product studio.  Pivots. Personal energy. Business energy. Ecommerce Space. Bootstrapping. First principles. Product idea ...
Charging for Onboarding
23 Feb 2024
Contributed by Lukas
Launching a consultancy. Generating pipeline. Breaking limiting mindsets. Outsource vs. in-house SDRs. Paid customer onboarding. Daddy-daugh...
New Directions
16 Feb 2024
Contributed by Lukas
AI everywhere. Zuck's shots fired. Committing to the new direction. Customer success. "Starter for hire" consultancy concept. Skiing. Birt...
2024 Calculus
02 Feb 2024
Contributed by Lukas
Homepage experiments. Marketing is too expensive. Product-led growth. VC game. Bootstrapper game. Cold outreach. Over-correcting. Shingl...
Enough Time
19 Jan 2024
Contributed by Lukas
Customer Success. Offers product. Consulting aint so bad. Hiring a video editor. Redefining success. Not enough time. Ski trips with kids. ...
Pipeline Energy
12 Jan 2024
Contributed by Lukas
 Energizing the pipeline, energizing customer success, shipping a marketing site, unrealistic time estimations, getting snowed in, too much coffee (...
Blank Canvas
05 Jan 2024
Contributed by Lukas
New Year, new start, a blank canvas... Working more (or less). Clarityflow Commerce. New brand name. YouTube. Growing pipeline. Selling a ...
What would a young Jordan and Brian say?
15 Dec 2023
Contributed by Lukas
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? ...
Winning Partnerships
08 Dec 2023
Contributed by Lukas
Creator businesses. Self-serve demos. Partnership Gold. Stair-stepping. Sales process. Economy and SaaS. YouTube. Marketing in 2024. A...
Operating a Media Company
01 Dec 2023
Contributed by Lukas
Black Friday fun. Cold email. Sales teams. Product market fit. Website redesign. Media company operations. Audience funnels. Connect with Brian and Jo...
News Diets & Work Balance
17 Nov 2023
Contributed by Lukas
On today's episode: Our news diets and managing stress with world events New onboarding flows & outreach wins Board meeting dynamics SaaS viabili...
FOMO, Focus, and AI
10 Nov 2023
Contributed by Lukas
On today's episode: Brian goes public with his new thing for 2024... Jordan onboards & optimizes the new sales team Discovery channels vs. relati...
Compensation, Content, & Speed
03 Nov 2023
Contributed by Lukas
On today's episode: Sharing our real time stories publicly & transparently Compensation for sales teams vs. product teams Developing the content ...
Staring Reality In The Face
27 Oct 2023
Contributed by Lukas
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 Bri...
Product Growth Levers
15 Sep 2023
Contributed by Lukas
On today's episode: When does shipping product lead to growth? Muddy Metrics Sports, exercise, health, eating, and drinking habits Connect with Bria...
Getting Outside Help
08 Sep 2023
Contributed by Lukas
On today's episode: How we work with coaches & consultants to guide strategy & implementation UX hangover on shipped features Selling softwar...
Context Switching
25 Aug 2023
Contributed by Lukas
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...
Learning to do business (over and over)
11 Aug 2023
Contributed by Lukas
On today's episode: Building in public. Why and how? Learning sales. Process, strategy, tactics. How we learn and implement. A solo founder's dil...
An appropriate level of mud slinging
21 Jul 2023
Contributed by Lukas
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 person...
Launching mobile apps, sales cadence, and summer work-life.
07 Jul 2023
Contributed by Lukas
On today's episode: Brian's back from Asia (did he stop working?)Â Launching the Clarityflow app on iOS and Android (check the video) Jordan's shift...
Sales Breakthroughs & In-Person Growth Strategy
09 Jun 2023
Contributed by Lukas
On today's episode: The value of in-person relationship building The murky side of MRR growth Transparency with our teams PGA & LIV, Apple Visi...
High status vs. low status customers
02 Jun 2023
Contributed by Lukas
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 pl...
Founder Shadowing
19 May 2023
Contributed by Lukas
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 J...
Starting Up Sooner vs. Later
12 May 2023
Contributed by Lukas
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...
Knowing what we know now...
05 May 2023
Contributed by Lukas
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...
Hangovers & Chaos
28 Apr 2023
Contributed by Lukas
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 enterp...
Raising Funding (& Pricing)
21 Apr 2023
Contributed by Lukas
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 ...
Artificial Intelligent Business
29 Mar 2023
Contributed by Lukas
Random thoughts on what's happening in AI and startups. Jordan and co move to self-signups. Brian and co work on marketing projects. Jordan's business...
Websites & Taxes
22 Mar 2023
Contributed by Lukas
Both Jordan and Brian are in the thick of redesigning their SaaS websites. Plus some tax talk. Jordan's business, Rally Brian's business, Clarityflo...
ZipMessage has a new name...
14 Mar 2023
Contributed by Lukas
Brian shares the news rebranding ZipMessage to a new name and the transition roadmap ahead... And the new name is...Jordan and team step away to a con...
Putting in the hours
08 Mar 2023
Contributed by Lukas
Jordan and Brian both feel overworked this week. Putting in more hours than usual, and more importantly, strategizing on which priorities get those ho...
All the Things
23 Feb 2023
Contributed by Lukas
Another week in the chaos that is startup land for Brian and Jordan. Topics include: Starting and finishing our day Managing focus through dail...
Projections… What Are They Good For?
06 Feb 2023
Contributed by Lukas
The episode streak continues! Brian’s product design process, Jordan’s annual budget meeting (and takeaways), outbound vs. inbound marketing, and ...
Communicating What's Next
31 Jan 2023
Contributed by Lukas
This week, Brian and Jordan yap about: – Strategic partnerships – Pricing on transactions – Communicating company direction (internally...
Product in Market (Is How We Learn)
24 Jan 2023
Contributed by Lukas
Back for our weekly founder therapy session, err… podcast episode Here’s what’s up this week: – Brian (finally) ships sub-threads in Z...
Building in public… More.
18 Jan 2023
Contributed by Lukas
We kick off 2023 with a grab bag of topics: – Jordan’s building in public more – Brian’s building solo with contractors – Headless ...
Another Year
03 Jan 2023
Contributed by Lukas
We look back on the ups and downs in 2022 and look ahead to 2023. The emotional rollercoaster rolls on… Thanks for listening and for sticking wi...
Hey ChatGPT, what should we talk about?
13 Dec 2022
Contributed by Lukas
We asked ChatGPT to suggest some topics for today’s episode but it came up short. So you’ll have to settle for the boring human versions of Brian ...
Twitter Takes (and Some Business Talk)
09 Nov 2022
Contributed by Lukas
Our obligatory take on Twitter in the Elon era. Also: SEO, board meetings, and growth targets. What are your thoughts on Twitter in the time of...
Q4 Energy
17 Oct 2022
Contributed by Lukas
Jordan talks defining their category and stepping back into the sales demo seat. Brian launched a community strategy while big product plans are under...
Tools & People
28 Sep 2022
Contributed by Lukas
What tools do you use for sales and support? Which tools work best for project management? How do you know who to hire first if you’re a bootstrappe...
What We'd Build (If Not This)
20 Sep 2022
Contributed by Lukas
Brian and Jordan are back behind the mic and are powered by the chilly fall weather and some pretty strong cold brew. Are you ready for the most rando...
Work-Life (Hour-by-Hour), Explained
08 Sep 2022
Contributed by Lukas
What are the rocks in your life right now? How do you balance work and life? What are some good compartmentalizing tactics, so you can leave work at w...
Research, Roadmaps, People, and Product
31 Aug 2022
Contributed by Lukas
How do you figure out the next iteration of your business? What keeps you unemployable? Does your environment change your outlook on personal and prof...
Company as a Product
10 Aug 2022
Contributed by Lukas
How do you get rid of post-illness brain fog? How do you build company culture when you’re absent? What are your steps to shipping out features? ...
Product vs. Pipeline
11 Jul 2022
Contributed by Lukas
What has happened in the venture funding world in the past couple of months? How do you handle repositioning? Can you lean too heavily on your product...
Talking to Customers
07 Jun 2022
Contributed by Lukas
How do you avoid consistent churn with new products? What tools do you use to learn about your market? What influences the changes in your products? ...
Marketing in 2022
28 Apr 2022
Contributed by Lukas
Brian and Jordan are both in flux between school, stressing over work, selling houses, and MicroConf. They summarize their chaotic couple of weeks and...
Traction... Then what?
08 Apr 2022
Contributed by Lukas
How do you decide what features you should work on now? How do you stay unplugged during a vacation? What are the milestones and progress markers that...
Everything Must Go
08 Apr 2022
Contributed by Lukas
We have some big news to share before we go on a (much needed) two-week hiatus. Brian talks about his sale of Productize, in addition to nearly e...
CartHook Acquired!
06 Apr 2022
Contributed by Lukas
What do you get out of conferences? Do you mute competitors on Twitter? How to you utilize Twitter as a budding SaaS entrepreneur? After a brief hi...
Tokenizing
22 Feb 2022
Contributed by Lukas
How are you and your company changing with the times? Are you considering tokenizing your software company? Have you begun adopting web3 technology? ...
So Meta
09 Feb 2022
Contributed by Lukas
Brian and Jordan are having a great time as they ride good days, give great updates, and look forward to some exciting things in the near and far futu...
Wheels Are Turning
18 Jan 2022
Contributed by Lukas
Brian has sold ProcessKit! He explains the surprisingly stress-free and smooth process. Jordan talks about his upcoming move to Chicago. Meanwhile, th...
2021/2022 New Year reflections
18 Jan 2022
Contributed by Lukas
Brian’s product, ZipMessage, is live today on Product Hunt the same day this episode airs—Tuesday, January 11th
The Chaos
10 Jan 2022
Contributed by Lukas
Does experimentation affect your business and cause more stress within your leadership team? How are the communication levels within your team? How do...
Define Traction
10 Jan 2022
Contributed by Lukas
What does traction feel like? How do you authentically build a network? Brian and Jordan talk about marketing, website updates, and the different phas...
Chicken or Egg Development
08 Dec 2021
Contributed by Lukas
When launching a new SaaS business, what comes first? What features do you focus on? How do you keep an eye on your key metrics early on? How do you h...
Go to Market vs. Marketing
09 Nov 2021
Contributed by Lukas
What is the difference between going to market and marketing? What mindset do you need to be in to accomplish your goals for both of these stages of b...
How to Fund a Startup
09 Nov 2021
Contributed by Lukas
Jordan shares some big news, 5.8 million dollars worth of news. At the feet of the news of Rally’s seed funding announcement, Brian and Jordan talk ...
Should We Rename the Podcast?
27 Oct 2021
Contributed by Lukas
Bootstrapped Web is no longer bootstrapped, on either side! Jordan starts off this episode with his “coming out” strategy, which all starts wit...
Audience Ops Changes Hands
23 Sep 2021
Contributed by Lukas
Some news! Brian has sold his business, Audience Ops, to JD Graffam! And what better way to announce this transition than to bring JD on the sho...
Marketing ideas
19 Aug 2021
Contributed by Lukas
Introduction: Do you work with a full-service accounting and admin company? How do you create markers on your business’s path to success? What un...
Back and Running
05 Aug 2021
Contributed by Lukas
After a month hiatus, Brian and Jordan are back with stories about trips, waking up in pain, and prepping for competition. They also talk about growth...
Metrics & Hiring Funnels
24 Jun 2021
Contributed by Lukas
Brian and Jordan are back to back-to-back weeks before vacation and travel plans kick in because… It’s summertime! While Jordan deals with a minor...