# Ask Lenny vs Roley.ai

The clearest difference is in-app purchases: Roley.ai at none against Ask Lenny's 2. Roley.ai also leads on update cadence (every 11 days vs every 6 weeks). On price, ads, device support and iOS requirement there is nothing between them.

Both are free to download. Ask Lenny sells 2 in-app purchases, starting at $4.99 per month. Roley.ai asks for nothing beyond the download.

Ask Lenny ships an update every 6 weeks, Roley.ai every 11 days. The most recent releases landed on October 30, 2026 and October 9, 2026 respectively.

## The numbers

| Metric | Ask Lenny | Roley.ai |
| --- | --- | --- |
| Price | Free | Free |
| Rating | **[5.0 (14 ratings)](https://appshunter.io/ios/app/ask-lenny/id6478363423/reviews)** | — |
| Number of ratings | **14** | — |
| Positive reviews | 100.0% of reviews | — |
| In-app purchases | Yes | **No** |
| Ads | No | No |
| Update frequency | Every 6 weeks | **Every 11 days** |
| Monetization | Freemium | — |
| Size | 50 MB | 61 MB |
| Requires iOS | **14.0.0** | 15.1 |
| Devices | iPhone, iPad, iPod | iPhone, iPad, iPod |
| Age rating | 17+ | 4+ |
| Developer | [Lenny Gray](https://appshunter.io/developer/1732620106) | [Roley.ai CORP](https://appshunter.io/developer/1773560322) |

## What reviewers say

### Ask Lenny

[App page](https://appshunter.io/ios/app/ask-lenny/id6478363423)

Access proven door-to-door sales techniques and tips from an industry legend. This app offers comprehensive guidance across 16 categories and over 67 sub-categories, with audio and text content to help you succeed.

**Highlights:** Door-to-door sales techniques, 16 sales categories, 67+ sub-categories, Audio and text content, Search functionality, Expert insights

**Features:** macOS Compatibility, Vision Pro support

**In-app purchases (2)**

| Purchase | Price | Billing |
| --- | --- | --- |
| Pro Monthly | $4.99 | per month |
| Pro Annual | $49.99 | per year |


### Roley.ai

[App page](https://appshunter.io/ios/app/roleyai/id6736864219)

**Features:** macOS Compatibility, Vision Pro support

**In-app purchases:** none


## Frequently asked questions

### Is Ask Lenny free?

Ask Lenny is free to download, with in-app purchases available.

### Is Roley.ai free?

Roley.ai is free to download, with no in-app purchases.

### Do Ask Lenny or Roley.ai have ads?

Neither Ask Lenny nor Roley.ai shows ads.

### Which is updated more often, Ask Lenny or Roley.ai?

Ask Lenny ships an update every 6 weeks, and Roley.ai every 11 days. Most recently, Ask Lenny was updated on October 30, 2026 and Roley.ai on October 9, 2026.

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*Compared by [AppsHunter](https://appshunter.io/) from daily US App Store data. Review summaries are generated from verbatim App Store reviews.*