# Neil Wainwright

> Neil Wainwright is a seed investor at UpHabit backing Mobile Apps and Artificial Intelligence. See 4 investments, check sizes, portfolio. Updated Aug 2026.

- Type: Angel Investor
- Fund: [UpHabit](https://shizune.co/investors/profile/uphabit)
- Location: Toronto, Canada
- Total investments: 4
- Last investment: Feb 2023
- Lead investor: 0%
- Last updated: Aug 2026
- LinkedIn: https://www.linkedin.com/in/neilwainwright
- X (Twitter): https://twitter.com/neildwainwright
- Facebook: https://www.facebook.com/search/top/?q=Neil%20Wainwright

Neil Wainwright is a seed investor at UpHabit in Toronto focused on Mobile Apps and Artificial Intelligence. Neil Wainwright is the Founder and CEO of UpHabit.

## Round sizes

| Stage | Round size |
| --- | --- |
| Seed | $446k–$912k |

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| Mobile Apps | 2 | 50% |
| Artificial Intelligence | 2 | 50% |
| B2B | 1 | 25% |
| B2C | 1 | 25% |
| Travel | 1 | 25% |

16 industries tracked in total.

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Seed | 3 | 75% |
| Angel | 1 | 25% |

### Country

| Country | Investments | Share |
| --- | --- | --- |
| Canada | 2 | 50% |
| United States | 1 | 25% |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| Pilot | “Travel is a trillion-dollar industry stuck in the past. The last major breakthrough came in the 1990s, with the emergence of online travel agencies (OTAs) like Booking.com and Expedia to aggregate inventory.” -a16z Consumer, 2023Since then, everything's been built for vendors to sell inventory, not for the people buying it. Even now, rigid,slow moving OTAs are building (and failing at) primitive AI chat to push inventory, not help you plan.People are frustrated, but they don’t want travel agents. They want better tools. 90% of Americans say travel planning is tedious and costly (time/money/stress), but only 20% prefer travel agents, because most don’t want a salesperson planning their trip. After speaking with hundreds of travellers, they’ve told us they want the value of a travel agent, without using onePlanning and booking a vacation shouldn’t feel like another job. It should be: - Collaborative – Easy to plan with friends, without endless group chats - Simple – One tool to discover, organize, and book—beautifully - All in One – No more tabs, texts, or patchwork spreadsheets - Free, Fun, and Flexible – Because planning should feel like part of the adventureIntroducing Pilot: An AI powered productivity tool facilitating end to end travel. Unlike competitors, Pilot is: - Personalized, flexible and collaborative for any trip - User-friendly, free, and fun, especially with friends or a group - A discovery and planning tool first, a booking tool secondPilot replaces travel agents by letting you “talk” to your trip, learning and improving based on your preferences as you use it (like Netflix). AI agentic workflows then automatically syndicate, summarize, map, visualize, share, organize, and book plans, in an increasingly personalized way.It's everything you need to make trips happen (and share them) in one place.Product vision: To become the full-stack platform for global travel, giving you the value of a travel agent, without needing one. | $226K | Angel | Feb 15, 2023 |  |
| Pilot | “Travel is a trillion-dollar industry stuck in the past. The last major breakthrough came in the 1990s, with the emergence of online travel agencies (OTAs) like Booking.com and Expedia to aggregate inventory.” -a16z Consumer, 2023Since then, everything's been built for vendors to sell inventory, not for the people buying it. Even now, rigid,slow moving OTAs are building (and failing at) primitive AI chat to push inventory, not help you plan.People are frustrated, but they don’t want travel agents. They want better tools. 90% of Americans say travel planning is tedious and costly (time/money/stress), but only 20% prefer travel agents, because most don’t want a salesperson planning their trip. After speaking with hundreds of travellers, they’ve told us they want the value of a travel agent, without using onePlanning and booking a vacation shouldn’t feel like another job. It should be: - Collaborative – Easy to plan with friends, without endless group chats - Simple – One tool to discover, organize, and book—beautifully - All in One – No more tabs, texts, or patchwork spreadsheets - Free, Fun, and Flexible – Because planning should feel like part of the adventureIntroducing Pilot: An AI powered productivity tool facilitating end to end travel. Unlike competitors, Pilot is: - Personalized, flexible and collaborative for any trip - User-friendly, free, and fun, especially with friends or a group - A discovery and planning tool first, a booking tool secondPilot replaces travel agents by letting you “talk” to your trip, learning and improving based on your preferences as you use it (like Netflix). AI agentic workflows then automatically syndicate, summarize, map, visualize, share, organize, and book plans, in an increasingly personalized way.It's everything you need to make trips happen (and share them) in one place.Product vision: To become the full-stack platform for global travel, giving you the value of a travel agent, without needing one. | $446.1K | Seed | Feb 15, 2023 |  |
| Wishroute | Wishroute helps D2C companies proactively and personally support customers with a human “accountability buddy," driving increased conversion, engagement and retention. We enable companies to add human-supported daily SMS conversations to their platforms, designed to help people build healthy habits around the product they signed up for,increasing motivation and, in turn, preventing drop-off. We leverage AI to turn our human support guides into superhumans, with the ability to handle any scale and deliver a positive ROI. |  | Seed | Sep 13, 2021 |  |
| LumiQ | LumiQ is a native podcast app where engaging conversations with business leaders count as verified CPD/CPE for CPAs. | $911.5K | Seed | May 21, 2021 |  |

4 of 4 investments shown.

## Co-investors
- [AngelList Quant Fund](https://shizune.co/investors/profile/angellist-quant-fund) — VC Fund, 1 deal together
- [Neu Ventures](https://shizune.co/investors/profile/neu-ventures) — VC Fund, 1 deal together
- [Oridun Capital Management](https://shizune.co/investors/profile/oridun-capital-management) — VC Fund, 1 deal together
- [TBD Angels](https://shizune.co/investors/profile/tbd-angels) — VC Fund, 1 deal together
- [Techstars](https://shizune.co/investors/profile/techstars) — VC Fund, 1 deal together
- [The Roux Institute Techstars Accelerator](https://shizune.co/investors/profile/the-roux-institute-techstars-accelerator) — VC Fund, 1 deal together

## About UpHabit

VC Fund · Toronto, Canada

UpHabit is the relationship management app that you need. Finally you can set regular reminders, make notes, and remember the little things.

1 contacts available at UpHabit.

| Name | Title | Profile |
| --- | --- | --- |
| Neil Wainwright | Founder and CEO | https://shizune.co/investors/profile/neil-wainwright |

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## FAQ

### What does Neil Wainwright invest in?

Neil Wainwright invests primarily in Mobile Apps, Artificial Intelligence and B2B startups, most often at Seed and Angel stage. Most of the 4 investments tracked by Shizune back companies in Canada. The Investment Focus section breaks down every industry, stage and country in the portfolio.

### What is Neil Wainwright's check size?

Neil Wainwright typically joins rounds of $446k–$912k at Seed. These ranges are 10th–90th percentile round sizes calculated from confirmed public funding rounds, so they are a realistic guide to the rounds Neil Wainwright participates in.

### When did Neil Wainwright last invest?

The most recent investment recorded for Neil Wainwright closed in Feb 2023. Shizune tracks 4 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.

### Is Shizune's investor data accurate?

Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.

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