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Build a mobile app or stay web only?
I'm deciding whether to build a mobile app for my existing web software. My most active users have been requesting it, but it would take 3 to 4 months of engineering time and I'm the only developer. The web product has 400 paying customers and fewer than 2% cancel each month.
Launch a free plan or keep it paid only?
I'm considering adding a free plan to my $49/month software. I currently have 120 paying customers and want to grow faster. I worry a free plan will reduce paid sign ups, but it could bring in far more new users at the top of the funnel.
Hire my first employee or stay solo?
I'm a solo founder with $180,000 in annual revenue deciding whether to hire my first full time employee. I've handled everything myself for 18 months and I'm at capacity. Hiring would cost $80,000 per year and reduce my cash runway by 18 months.
Outsource content creation or keep writing myself?
I'm considering hiring a part time content writer at $2,500/month versus continuing to write content myself at 4 hours per week. My organic traffic has been stuck at 8,000 monthly visitors for 6 months despite consistent posting.
Focus on one niche or stay broad?
I've built a general project management tool used by 300 companies across many industries. I'm deciding whether to focus exclusively on construction companies, where I have 40 customers and very high satisfaction scores, or continue serving all types of businesses.
Raise outside funding or keep bootstrapping?
My software has 60 customers paying $200/month. I'm deciding whether to raise $1 million from investors or continue funding the business myself. I have 14 months of cash left and clear product market fit in a specific niche, but growth is slow.
Invest in paid ads or organic content?
I'm allocating $3,000/month in marketing budget. I must choose between running paid Google and Meta ads, where a $500 test got me a $120 cost per new customer, versus investing in long form SEO content that would take 6 to 12 months to show results.
Build in public or stay private during early stage?
I'm launching a new developer tool and deciding whether to share my journey publicly on social media, or stay private until I have stronger proof that people want what I'm building. I currently have 200 followers and no launch deadline.
Add annual pricing or keep monthly subscriptions only?
I'm adding an annual payment option at $239/year (a 31% discount) alongside my current $29/month plan. I have 280 monthly subscribers who stay on average 8 months before cancelling. I need to weigh the lower revenue per customer against better retention.
Raise prices for new customers or hold steady?
I'm deciding whether to raise my software price from $49 to $79 per month for new customers only, while keeping existing customers on their current price. My main competitor charges $99/month and I have never raised prices in two years.
Pivot to business customers or double down on consumers?
My consumer app has 5,000 users but only 2% pay at $4.99 per month. Three companies have reached out asking if I would build a business version. I'm deciding whether to pursue the business opportunity or keep growing the consumer product.
Shut down the product or give it 6 more months?
I launched a productivity app 12 months ago. It has 800 free users but only 12 paying customers at $19/month. Despite 6 rounds of product changes I have not improved conversion. I'm deciding whether to shut it down or commit 6 more months to finding what works.
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