100 "Easier" Tips for Bootstrapped Business

Market (1–18)#

1. Markets with public data (installs, reviews, rankings) > opaque markets. You can measure the competition before you start.
2. Customers paying in strong currencies > low purchasing power. Same work, 5–10× the revenue.
3. Selling picks and shovels to a growing crowd > joining the crowd. Sell to newsletter writers instead of becoming one.
4. An existing budget line > a new budget. "Switch from X" is one decision. "Start paying for something new" is two.
5. Customers angry at the leader > happy customers. Watch for price hikes, acquisitions, sunsets and bad redesigns. Those months are open doors.
6. Growing market > shrinking market. In a shrinking market you can only steal share.
7. Boring market > hot market. Hot markets get 50 funded competitors within 6 months.
8. Too small for VCs > big market. A $2M/year niche changes your life and funded startups don't even see it.
9. B2B > B2C. Businesses pay more, churn less, and deduct it as an expense.
10. A product that makes the buyer money > one that only costs them. A purchase with clear ROI justifies itself.
11. A platform ecosystem (WP, Shopify, Stripe, Claude) > standalone. Buyers, search and trust come built in. The cost is platform risk. (Tyler Tringas)
12. A new marketplace in its first year > a mature one. Little competition, and the platform promotes early apps.
13. Unbundling one feature from a bloated tool > building a suite.
14. A need with a deadline (a law, compliance, a platform deprecation) > a nice-to-have. Deadlines force purchases.
15. Recurring pain > one-time pain. Recurring pain pays recurring revenue.
16. Daily-use product > yearly-use product. Frequency brings habit and retention.
17. Niche down until it hurts > starting broad. Expand later from a stronghold.
18. Low-regret purchase (cheap to try, easy refund) > high-stakes purchase. Cheap to try means a fast yes.

Customers (19–30)#

19. Customers you've been, or served for years > imagined customers. You already speak their language.
20. Customers gathered in one place > scattered customers. One community or marketplace is one query.
21. Customers who talk to each other > isolated customers. Word of mouth needs a network.
22. A clear job title > "anyone who…". A job title is something you can search for.
23. Owner = buyer = user > buying by committee. You need one yes instead of five.
24. People who already pay for software > people who never pay for tools.
25. Pros > beginners. Pros help themselves. Beginners generate more support tickets per dollar.
26. They search for the solution by name > you have to describe the problem. The search volume already exists.
27. Past behavior > future promises. "Would you buy?" tells you nothing. "What did you pay last time?" tells you a lot. (Rob Fitzpatrick, The Mom Test)
28. Reading where they complain > asking them. Forums, Reddit, reviews. (Amy Hoy, Sales Safari)
29. Pre-sales or deposits > surveys. Money is the only real vote.
30. Competitors' 1–3 star reviews > brainstorming. A free list of what the "Y people" hate.

Product (31–50)#

31. One product, one job > many jobs.
32. Copy a proven UX and change one thing > invent a new UX. Users don't want to learn.
33. Plugging into what they already use > a new app they have to adopt.
34. Selling the outcome > selling the tool. "Your first 1,000 subscribers" beats "newsletter plugin."
35. Done-for-you > do-it-yourself. At high prices, people pay for results.
36. Manual first (concierge) > automating first. Automate only what you've done 20 times. (Paul Graham: "do things that don't scale")
37. Shipping in weeks > months. The market answers faster than thinking does.
38. A boring stack you know > a new stack.
39. Opinionated defaults > endless options. Every setting becomes a support ticket.
40. A narrow environment (hosted) > endless environments. A theme runs on 10,000 different setups, which means endless bugs.
41. Their data lives in your product > a stateless tool. Data is switching cost.
42. Gets better with use > stays the same.
43. Visible output (a site, an email, a report) > invisible value.
44. A built-in loop ("Sent with X") > no loop. Every output is an ad.
45. An import/migration tool > "start fresh." It removes the #1 reason not to switch.
46. Time to first value in minutes > more features.
47. Small support surface > large. Support is the hidden cost that kills solo businesses.
48. A free tool or generator as marketing > blog posts. (Traction: engineering as marketing)
49. Building for 1 perfect customer > building for the average of 100.
50. Deleting features > adding them. Less code, less support, a clearer pitch. (37signals)

Pricing and business model (51–65)#

51. Charging from day 1 > free now, money later.
52. Higher price > low price. You need fewer customers, you get better ones, and support costs less per dollar. (patio11: "charge more")
53. Recurring > one-time.
54. Annual prepay > monthly. Cash up front, lower churn.
55. Price that grows with the customer (subscribers, sites, seats) > flat price. Expansion revenue cancels out churn.
56. 3 tiers > 1 or 10.
57. Free trial > freemium, unless distribution is free. Freemium needs an enormous top of funnel.
58. Freemium on wp.org is the exception. The free distribution pays for the free tier.
59. 10 customers × $1,000 > 1,000 × $10 at the start. You can reach 10 by hand.
60. Payback within 1 month > a long CAC payback. A bootstrapper can't fund the gap.
61. No lifetime deals > lifetime deals. They give you cash now and support forever, with no recurring revenue.
62. Raising prices for new customers and keeping old customers' price > never raising. Most indie products are underpriced.
63. Productized service (fixed scope, fixed price) > custom work. (Brian Casel)
64. Service first, then product > a product from zero. You get paid while learning what to build.
65. Selling to people already paying a competitor > converting people who've never paid.

Channel (66–84)#

66. One channel mastered > five half-done. (Traction's Bullseye; Rob Walling)
67. Going where attention already is > building an audience from zero, at least at the start.
68. A marketplace with buyer intent > your own site at the start. It's rented, but the buyers are already shopping.
69. Intent channels (search, marketplaces) > interruption channels (ads, social).
70. Bottom-of-funnel keywords ("X alternative", "X vs Y", "best X for Y") > top-of-funnel content.
71. Comparison pages > generic blog posts.
72. Borrowing someone's audience (partners, affiliates, KOLs) > building your own first. This is the "index" from the database encoding.
73. Agencies and freelancers > end customers one at a time. One agency can mean 20 sites.
74. Integrations > ads. You get listed in the bigger tool's directory.
75. Direct outreach for the first 100 > SEO. Feedback in days instead of months.
76. Answering where they ask (forums, support threads, groups) > broadcasting.
77. Customer stories > your own claims.
78. A free resource that captures email > "subscribe to my newsletter."
79. An email list > followers. No algorithm can take it away.
80. Many small launches (every feature) > one big launch.
81. Being named and compared in writing > being the best but invisible. AI answers recommend what's documented, compared and listed.
82. A unique brand name > a generic one. You can search for it, rank for it and trademark it.
83. Your existing customer list for product #2 > a cold launch. It's the cheapest channel you own.
84. Building in public (only if your customers are makers) > building in secret.

Sales and retention (85–92)#

85. Onboarding calls with early customers > self-serve only. You learn what breaks.
86. Migrating them yourself > telling them how. (Nathan Barry, ConvertKit)
87. Fixing churn > more acquisition. Don't fill a leaky bucket.
88. Talking to customers who left > guessing why.
89. Upselling existing customers > finding new ones.
90. The founder answering support > a ticket queue. Big players can't copy fast and personal.
91. A cancel flow that asks why > a silent cancel.
92. Same audience, new product > same product, new audience. The trust and the channel are already there. (Awesome Motive)

Founder (93–100)#

93. Low burn > big funding. More months means more attempts.
94. Keeping a cash cow while exploring > burning the boats.
95. Buying a small existing business > building from zero. Revenue, customers and SEO from day 1. (Andrew Wilkinson; Acquire.com)
96. Adopting or buying a plugin that already has users > starting at 0 installs.
97. Solo-sized problems > team-sized ones (24/7 uptime, enterprise sales, heavy compliance).
98. A portfolio of small bets with kill rules > one huge bet. (Daniel Vassallo)
99. Kill criteria set before you start > deciding later. Sunk cost will lie to you.
100. A market you'd enjoy for 10 years > a hot trend. Motivation is runway too.

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Most relevant to the newsletter-in-WordPress product: #5, #10, #44, #45 with #86, #55, #70, #73, #75, #83, #96.