Time Tracking App - Solo Founder with Low Infrastructure Costs

Trial vs Freemium: Time Tracking App for Solo Founder

Bottom Line: Use 14-Day Free Trial WITHOUT Card Upfront

Why this fits YOUR situation:

1. Your 8-month runway is critically tight: You need revenue NOW. Freemium takes 9-12 months to optimize profitability. Trial converts in 14-30 days, but card-upfront would reduce signups by 30-40%. You can’t afford to lose leads OR wait months for revenue.

2. Your cost structure is phenomenal: At $1/user/month, you have the lowest cost-to-serve in the industry. This changes everything. Even with 1,000 free trial users over 14 days, you’re only spending ~$460 in infrastructure ($1 × 1,000 users × 14 days / 30 days). This is manageable.

3. Ultra-fast time-to-value is your superpower: “Click start, click stop” means users understand your value in 30 seconds. They don’t need exploration time—they need proof it works. 14 days gives them 28x more time than needed.

4. Solo founder support reality: Simple product = minimal support burden. Time tracking has fewer “how do I?” questions than complex SaaS. You can handle trial volume without card filtering.

The twist: Your situation is unusual. Most founders with 8-month runway should avoid freemium entirely. But your $1/user cost is so low that you can afford NO-CARD trial (higher signups) instead of CARD-UPFRONT trial (fewer signups but higher intent). This gets you volume AND speed.

What You’re Signing Up For

With 14-Day No-Card Trial:

✅ Fast conversions: First revenue in 2-4 weeks
✅ Maximum signup volume: No card friction means 2-3x more trials than card-upfront
✅ Low cash exposure: Even at scale, $1/user/month × 14 days = $0.47 per trial user
✅ Qualified by action, not credit card: Users who actually track time are your signal
✅ Room to experiment: Low cost means you can test 14-day vs 7-day vs 21-day trials

❌ Some tire-kickers: Without card requirement, ~20-30% will never intend to pay
❌ Email dependency: Must convert via email drip since no billing relationship yet
❌ Urgency required: Need strong trial expiration messaging to drive conversions
❌ Slight delay to revenue: Card-upfront charges immediately; no-card requires active upgrade decision

Why not freemium?

Even with low costs, freemium is a mistake:

• ❌ 8-month runway is too tight: Freemium takes 9-12 months to hit 3-5% conversion rates
• ❌ “Free forever” reduces urgency: No trial countdown = users procrastinate upgrading
• ❌ Feature pressure: Free users demand features (“why isn’t export free?”) you can’t monetize
• ❌ Positioning problem: Simple products struggle to justify paid tiers vs “free forever”

Why not card-upfront trial?

Card-upfront would reduce your signups by 30-40%:

• With 8 months left, you need VOLUME of conversions, not just high intent
• Your $9/month price point is low enough that you should maximize trial starts
• At $1/user cost, you can afford the “cost of curiosity” for tire-kickers

Case Studies: Bootstrapped Time Tracking Apps

Clockify (Freemium - Eventually Successful, But Long Road)

• Founder: Nenad Milanović, bootstrapped (no VC)
• Model: Generous freemium (free forever, unlimited users)
• Timeline: Founded 2017, hit 17,000 users in 5 days, reached $26.4M revenue in 2023
• Team: Started with 8 people funded by existing freelance cash flow (NOT solo)
• Result: Massive success, BUT…
• Critical context: Had existing revenue from freelancing to fund 3-month build + team of 8. Not a solo founder burning savings.
• Lesson for you: “Clockify could afford freemium because Nenad had cash reserves from 10 years of freelancing. He wasn’t burning runway on a timer. You are.”

RescueTime (Trial-Only - Consistent Growth)

• Founders: Joe Hruska & Brian Fioca (2008, Y Combinator)
• Model: Trial-only (14-day free trial), NO freemium tier
• Pricing: $12/month or $78/year
• Result: Bootstrapped to 1M+ customers, $2.6M revenue (2024)
• Timeline: Launched 2008, steady revenue growth, hit profitability early
• Quote insight: “Beyond a short trial, the only option is one paid plan. No free tier.”
• Lesson: “Trial-only worked for 16+ years. No freemium needed. Simple product = trial is enough.”

Toggl Track (Hybrid - But Resource-Heavy)

• Model: Free plan (5 users max) + Premium ($10/user/month) + Enterprise (custom)
• Success: Industry leader, huge user base
• Cost to user: Free plan is LIMITED (5 users, basic features)
• Lesson: “Toggl’s ‘free’ is really a trial in disguise—capped at 5 users forces teams to upgrade. Not true freemium.”

Harvest (30-Day Trial - No Card Required)

• Model: 30-day free trial, full features, NO credit card required
• Founded: 2006 (bootstrapped)
• Differentiator: Built-in invoicing (added value beyond time tracking)
• Result: Industry standard for freelancers/agencies
• Lesson: “30-day no-card trial works when your product has clear ROI. Harvest proves it for services billing.”

Your 90-Day Action Plan

Month 1: Build & Launch Trial

Week 1-2: Implementation

• Build 14-day trial with email collection (NO card required)
• Add trial countdown to dashboard (“12 days left in trial”)
• Set up Stripe checkout for manual upgrade (one-click from dashboard)
• Create trial expiration logic (downgrade to view-only mode after 14 days)

Week 3-4: Email Drip Sequence

• Day 0: Welcome email + “Start your first timer now” CTA
• Day 2: Quick win email (“You’ve tracked 3 hours—here’s what you’re learning about your time”)
• Day 7: Midpoint email (“You’re halfway through—unlock reports with Premium”)
• Day 11: Urgency email (“3 days left—upgrade now to keep your data”)
• Day 13: Final notice (“Trial ends tomorrow—here’s what happens to your account”)
• Day 15: Post-trial email (“Your trial expired—upgrade to resume tracking”)

Month 2: Measure & Optimize

Track these metrics DAILY:

• Trial signup rate (% of visitors who start trial)
• Trial activation rate (% who track at least 1 hour)
• Trial-to-paid conversion rate (target: 10-15% for no-card trial)
• Time-to-first-track (faster = better engagement)

Optimization experiments:

• A/B test trial length: 14 days vs 10 days vs 7 days
  • Hypothesis: 7 days might work since TTV is 30 seconds
• Test email send times (morning vs evening)
• Add in-app upgrade prompts at key moments:
  • After tracking 10 hours: “You’re a power user—unlock reports for $9/month”
  • After 7 days: “You’ve built the habit—make it permanent”

Month 3: Conversion Tactics

Add urgency and value signals:

• Countdown widget: Persistent banner showing “X days left” in dashboard
• Feature teases: Show locked Premium features (reports, exports, team features) with upgrade CTA
• Social proof: “Join 247 people who upgraded this month”
• One-time offer: Email Day 13 with “Upgrade today, get first month for $5” (50% off)
• Manual extensions: For engaged users who email asking for more time, extend trial 7 days (builds goodwill, signals value)

Post-trial nurture sequence (for users who don’t convert):

• Day 16: “Miss your data? Here’s what you tracked last week” (nostalgia hook)
• Day 23: “One week without tracking—here’s what you’re losing”
• Day 30: “Last chance: 20% off if you upgrade this week” (discount)

The Cash Flow Reality

Let’s model your first 6 months with your 8-month runway and $2K/month burn:

14-Day No-Card Trial (10% conversion - conservative for no-card):

To hit break-even ($2K MRR to cover burn):

• Need 222 paying customers ($2,000 / $9)
• At 10% conversion, need 2,220 total trials
• At 400 signups/month, you hit this in Month 8 (within your runway!)

Freemium Alternative (DON’T DO THIS):

Interpretation:
Trial gets you to break-even by Month 7-8. Even with $1/user costs, freemium keeps you underwater indefinitely. Your runway can’t absorb it.

When to Reconsider

Stick with trial until:

• You hit $5K+ MRR (covering burn + some profit)
• You validate product-market fit (steady signup growth)
• You have 3-6 months runway buffer beyond break-even

Consider adding limited free tier LATER if:

• You hit $10K+ MRR and have cash cushion
• You add viral/team features (team time tracking, shared reports)
• Competition shifts heavily to freemium and signups drop

But here’s the thing: For ultra-simple products, freemium often isn’t necessary. RescueTime has thrived 16 years without it.

Final Word

You asked if $9/month pricing is a “no-brainer decision.” Yes, but not because of pricing—because of your cost structure.

At $1/user/month, you have more flexibility than 95% of SaaS founders. You can afford no-card trials at scale. You can test, iterate, and optimize without burning through runway.

Your advantage isn’t just simplicity—it’s economics.

Use it. Launch 14-day no-card trial. Get to 100 signups in Month 1. Hit 10-15% conversion. Reach $2K MRR by Month 7-8. Extend your runway by reducing burn or getting to profitability.

Don’t overthink it. Your product is simple. Your costs are low. Your pricing is fair. Just ship the trial.