If you run a paid Substack and want your subscribers to hang out in a private Discord server, there are really only two tools purpose-built for this job: StackPass (that's us) and Sidestack.io. Everything else — Memberful, Whop, Patreon — treats the Substack-specific use case as an afterthought.
Sidestack has been around longer and has more customers today. StackPass is the challenger, launched in April 2026 by a team of two — me (Michael Sikand, a Forbes 30 Under 30 media founder) and my co-founder Alex. This post is going to be as honest as I can make it. If Sidestack is the better fit for you, pick Sidestack.
The 30-second verdict
- Pick Sidestackif you want the product with the longest track record and you also sell digital downloads via Substack's “Buy Buttons.”
- Pick StackPassif you want the tool that's focused entirely on Discord community sync, costs less at every subscriber count, and lets you grow without forcing an upgrade before you're ready.
Pricing
This is the biggest practical difference, and it's where StackPass is deliberately priced below Sidestack at every stage.
| Plan | StackPass | Sidestack |
|---|---|---|
| Free trial | 14 days, card required | 7 days |
| Entry tier | $19/mo ($15/mo billed annually) | $39/mo flat |
| Entry tier subscriber cap | 1,000 paid subscribers | Unclear (no published cap) |
| Scale tier | $49/mo ($39/mo annually) — unlimited | N/A (flat single plan) |
| Annual discount | 20% | None published |
If your paid community has under 1,000 active subscribers, you're paying $19/month on StackPass vs $39/month on Sidestack. That's $240 a year saved on a comparable tool. Even at the Scale tier, StackPass is $10/month cheaper than Sidestack's Business tier — and unlike Sidestack, StackPass gives you room to grow into it.
What they do better
Sidestack has a few things going for them:
- Buy Buttons for digital products.Sidestack lets you sell eBooks, courses, and other files (up to 50GB) directly on your Substack page. StackPass doesn't do this — we focused the product entirely on Discord sync.
- A public creator directory.Sidestack.io hosts a browsable index of Substacks and lets creators pay $49 for a 30-day featured slot. That drives meaningful extra discoverability. StackPass doesn't have a directory yet, though it's on our near-term roadmap.
- Track record.They've been doing this since 2023. They have testimonials, case studies, and battle-tested infrastructure.
Where StackPass is better
Price that grows with you, not ahead of you
Sidestack charges $39/month whether you have 50 paid subscribers or 5,000. That's a great deal at 5,000 — and a painful markup at 50. StackPass is deliberately priced so small creators pay less and scale creators pay a little more. Fair both ways.
Real-time webhook sync
StackPass listens to customer.subscription.updatedevents from Stripe and grants or revokes the Discord role within seconds of a subscription change. A nightly reconciliation job catches any event we missed. Sidestack's sync cadence isn't publicly documented; based on user reports it's also quick, but we've engineered the latency deliberately.
We never revoke a role you granted manually
If you cancel StackPass, we stop syncing new subscriptions but we nevermass-revoke Discord roles that were previously granted. Your paying subscribers keep their access until you (or your Discord server) explicitly change it. Same goes when a creator hits a plan limit — existing subscribers are never affected; only new role grants pause.
Honest auto-upgrade, with 48 hours' notice
If your subscriber count crosses 1,000 and you're on the Creator plan, we auto-upgrade you to Scale — but only after emailing you 48 hours before and only if you're over the limit for three consecutive days. You can opt out of auto-upgrade entirely from your billing settings.
Built in public, with an indie-hacker ethos
StackPass is built by a two-person team. When you email hello@getstackpass.com, one of us replies — usually within a few hours. At $49/month you get a direct channel to me (Michael), not a ticket in a queue.
Feature parity matrix
| Feature | StackPass | Sidestack |
|---|---|---|
| Auto-assign Discord role on subscribe | ✅ | ✅ |
| Auto-revoke on cancel | ✅ | ✅ |
| Works with existing Discord server | ✅ | ✅ |
| Stripe Connect integration | ✅ | ✅ |
| Multi-tier role mapping | Roadmap (Scale tier, Q3 2026) | Unclear |
| Sell digital downloads (Buy Buttons) | ❌ (not our focus) | ✅ |
| Public creator directory | Roadmap | ✅ |
| 14-day free trial | ✅ | ❌ (7 days) |
| Annual discount | 20% off | ❌ |
| 14-day money-back guarantee | ✅ | Unclear |
Who should pick which
Go with Sidestack if: you need Buy Buttons for digital products AND you want a tool with a longer track record AND the flat $39 pricing makes sense for your community size.
Go with StackPass if:you just want the best Discord sync for your Substack paid subscribers, you'd rather pay proportionally to your community size, and you want to support a small team that treats this as their primary product rather than one feature among many.
Try StackPass free for 14 days
No risk — 14-day free trial, 14-day money-back guarantee if you decide it's not for you. We'll email you 3 days before your trial ends so there are no surprise charges. It takes about five minutes to connect Stripe, install our Discord bot, and share your unique subscriber link.