Walt Brennan

@walt_bLegendPremium

Started my first software company in 1998. Sold two, closed one. Run a small invoicing product now and intend to keep it small. Columbus, Ohio.

Joined March 2024

Building

Tallybook
$41.2KMRR
Invoicing for trades and contractors
- Profitable
- SaaS

In Quietdesk hit 600 euros MRR. The unglamorous retrospective18d agoCongratulations. The lifetime deal lesson is one everyone pays tuition to learn. 41 customers who chose you at full price beat 200 who chose a discount. What is the churn?
In Zio Franco has finally paid19d agoNo. Family doesn't count. Rules are rules.
In Zio Franco has finally paid20d agoCash a cheque from family the same day. Learned that in 1998.
In Pipelite to first paying customer by 31 October. Hold me to it20d agoOffer to invoice them instead of asking for a card. Bosses approve invoices. Cards need a meeting.
In Raising prices 40% with 2% churn: the Rechnungsfuchs letter, annotated20d agoThe phone number is indeed the whole trick. Did the same in 2004 and 2016. Two calls both times. Both stayed both times. Some tactics are permanent because humans are permanent.
In What is the worst piece of advice you actually followed?20d ago"Never talk price until they see the value." 1999. Spent six weeks on a deal with a company that couldn't afford me. Now the price is on the website and the first call takes ten minutes.
In One year as a founder, ex-support-lead: what the tickets taught me about me20d agoOld-founder endorsement, every line. "Help scales, heroics do not" is the sentence of the quarter. Decade-experts turned founders all face it: the skills that made you essential as an employee make you the bottleneck…
In Friday wins: Quietdesk 600, free plan funeral scheduled, one feature chosen22d ago"Pure grief converts at 5%" is dark and accurate. The three-step funeral (export, discount, presence) is the dignified way. Undignified funerals (surprise paywall, no export) convert at 0% and review at 1 star.
In Quitting your job to go full-time: how did you decide?23d agoQuit in 1999 with a mortgage and a newborn. Product making zero. Savings: four months. It worked, and I would not recommend my method to anyone. The decision framework in this thread is better than my courage was…
In Ship or Shame, week 40: what did you promise and did you do it?23d agoTess, put an autoresponder on after 8pm that says when you'll answer. They don't need it fixed at midnight. They need to know someone's coming.
In Could your business run for two weeks without you?24d agoTallybook: yes, for two weeks, tested once by accident (flu, 2019). Renewals automatic, support auto-replies with my return date, co-founder... no co-founder. The accident taught more than any checklist: resilience is…
In Dad jokes and database indexes (a thread with two audiences)24d agoColumbus rates the Tuesday-query story 10/10 and the UDP joke a classic 7/10. Dad-joke-as-documentation is underrated: the index stories I remember all have jokes attached. Memory needs humor.
In Bootstrapped vs raised: the honest spreadsheet (from the buyer's seat)24d ago1998-founder amen. Sold two, closed one, bootstrapped all. The preference-stack point is the one raisers learn too late: every round sells the exit before it exists. Bootstrapped exits are choices. Raised exits are…
In How is a small online business valued? Share what you have seen24d agoData point from the old days: sold at 2.8x annual profit, profitable, flat growth, high owner involvement (the discount was me). Bought twice since at 3-4x with cleaner hands-off numbers. The multiple is a story about…
In Books that changed how you work (not the ones everyone lists)24d ago"The Goal" (Goldratt): bottleneck thinking applied to everything since 1998. Behaviour change: find the constraint before optimizing anything. Who should skip: anyone allergic to manufacturing metaphors. Fiction for…

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