# Tadayoshi Yoshida

> Tadayoshi Yoshida is a seed investor at Retired.com backing Software. See 10 investments, check sizes, portfolio and contact details. Updated Aug 2026.

- Type: Angel Investor
- Fund: Retired.com
- Location: Austin, United States
- Total investments: 10
- Last investment: Sep 2021
- Lead investor: 0%
- Last updated: Aug 2026
- LinkedIn: https://www.linkedin.com/in/henryyoshida
- X (Twitter): https://twitter.com/henryyoshida
- Website: https://x.com/henryyoshida
- Facebook: https://www.facebook.com/henry.yoshida

Tadayoshi Yoshida is a seed investor at Retired.com in Austin focused on Software and Financial Services. Tadayoshi Henry Yoshida is based out of Austin, Texas and is the Senior Vice President of Business Development of Retired.com. Tadayoshi previously worked at Rocket Dollar as a Co-founder and Chief Executive Officer. Tadayoshi Henry Yoshida attended the University of Texas at Austin.

## Contacts

5 contacts available for Tadayoshi Yoshida: work email, personal email, work phone, personal phone and socials. Sign up free to unlock them: https://app.shizune.co/sign-up/investor-profiles/find-email/henryyoshida?utm_source=investor_profile

## Round sizes

| Stage | Round size |
| --- | --- |
| Seed | $1M–$3.5M |
| Debt Financing | $185k–$750k |
| Convertible Note | $250k–$1.3M |

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| Software | 4 | 40% |
| Financial Services | 4 | 40% |
| Finance | 3 | 30% |
| SaaS | 2 | 20% |
| FinTech | 2 | 20% |

32 industries tracked in total.

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Seed | 3 | 30% |
| Debt Financing | 3 | 30% |
| Convertible Note | 2 | 20% |
| Angel | 1 | 10% |
| Series A | 1 | 10% |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| Rocket Dollar | Rocket Dollar lets people unlock IRA/401(k) money to invest in alternative/private assets such as real estate, crypto, startups, private equity, venture, and more with no taxes. | $8M | Series A | Sep 09, 2021 |  |
| Rocket Dollar | Rocket Dollar lets people unlock IRA/401(k) money to invest in alternative/private assets such as real estate, crypto, startups, private equity, venture, and more with no taxes. | $3.5M | Seed | Mar 27, 2019 |  |
| Oliver Technology Corporation | Oliver Technology Corporation is a SaaS Enabled Marketplace revolutionizing the way legal services in the financial industry are delivered. We've developed an integrated SaaS solution that allows banks to manage and oversee legal collections from beginning to end. In addition, the platform provides access to a marketplace of over 300 trainedattorneys across 15 states. | $1.3M | Convertible Note | Mar 03, 2017 |  |
| BlueCheck Inc | BlueCheck provides identity and age verification services through an internet based software application for online businesses. | $185K | Debt Financing | Feb 20, 2017 |  |
| Rabbet | Rabbet(https://rabbet.com/) is a real estate software company with two products: Rabbet Development and Rabbet Construction Lending. Our mission is to take the friction out of real estate development execution through structured, connected financial data. We help real estate teams turn fragmented project information into trustedinsights that can be shared, understood, and acted on throughout the development lifecycle.Rabbet Development (https://rabbet.com/developers/product-overview) is real estate development management software for owners, developers, and asset managers. It brings budgets, anticipated costs, draw schedules, and funding sources together across every phase of development, so teams always know where every project stands, answer questions without chasing information, and spot financial changes before they become project problems.Rabbet Construction Lending (https://rabbet.com/lenders/product-overview) is construction loan management software for banks, credit unions, and private lenders. It brings loan administration, documentation, draw review, and portfolio reporting into one system, so lending policies are applied consistently, portfolio risk is visible as projects evolve, and every funding decision is backed by the evidence and an audit trail required to move money. |  | Angel | Jul 25, 2016 |  |
| Vault | Vault provides the most comprehensive software platform in the market to address the financial burden of student loan debt. Our intuitive web-based tool provides a highly secure employee experience that empowers employees to achieve financial freedom. With the option to make contributions to employees’ debt repayment, Vault enables companies toattract and retain their valuable talent. Vault empowers companies with relevant, flexible products that provide advice, create pathways to manage student debt more effectively, and enable paying-down student loans while building 401(k) savings. | $3M | Seed | Feb 18, 2016 |  |
| Liveoak Technologies | Liveoak is a computer software company that specializes in cloud-based platform. It features a cloud-based software application platform that utilizes video conferencing, screen-sharing and data/ID capture with forms collaboration and e-signature capabilities that let your teams deliver white-glove service to your customers.The company wasfounded in 2014 and headquartered in Austin, Texas. | $605K | Debt Financing | Oct 11, 2015 |  |
| BlueCheck Inc | BlueCheck provides identity and age verification services through an internet based software application for online businesses. | $250K | Convertible Note | Oct 05, 2015 |  |
| Real Savvy | RealSavvy is the fastest growing all-in-on-platform for real estate brokers and agent teams. | $750K | Debt Financing | Sep 28, 2015 |  |
| Oliver Technology Corporation | Oliver Technology Corporation is a SaaS Enabled Marketplace revolutionizing the way legal services in the financial industry are delivered. We've developed an integrated SaaS solution that allows banks to manage and oversee legal collections from beginning to end. In addition, the platform provides access to a marketplace of over 300 trainedattorneys across 15 states. | $1M | Seed | Sep 10, 2015 |  |

10 of 10 investments shown.

## Co-investors
- [Central Texas Angel Network](https://shizune.co/investors/profile/central-texas-angel-network) — VC Fund, 4 deals together
- [Capital Factory](https://shizune.co/investors/profile/capital-factory) — VC Fund, 3 deals together
- [Sure Ventures](https://shizune.co/investors/profile/sure-ventures-4b28) — VC Fund, 2 deals together
- [Temerity Capital Partners](https://shizune.co/investors/profile/temerity-capital-partners) — VC Fund, 2 deals together
- [Corsa Ventures](https://shizune.co/investors/profile/corsa-ventures) — VC Fund, 1 deal together
- [Fenway Summer Ventures](https://shizune.co/investors/profile/fenway-summer-ventures) — VC Fund, 1 deal together

## About Retired.com

VC Fund



1 contacts available at Retired.com.

| Name | Title | Profile |
| --- | --- | --- |
| Tadayoshi Yoshida | Senior Vice President Business Development | https://shizune.co/investors/profile/henryyoshida |

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## FAQ

### What does Tadayoshi Yoshida invest in?

Tadayoshi Yoshida invests primarily in Software, Financial Services and Finance startups, most often at Seed and Debt Financing stage. Most of the 10 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.

### What is Tadayoshi Yoshida's check size?

Tadayoshi Yoshida typically joins rounds of $1M–$3.5M at Seed, $185k–$750k at Debt Financing and $250k–$1.3M at Convertible Note. These ranges are 10th–90th percentile round sizes calculated from confirmed public funding rounds, so they are a realistic guide to the rounds Tadayoshi Yoshida participates in.

### How do I contact Tadayoshi Yoshida?

Public channels for Tadayoshi Yoshida include LinkedIn, X (Twitter) and the website linked on this profile. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.

### When did Tadayoshi Yoshida last invest?

The most recent investment recorded for Tadayoshi Yoshida closed in Sep 2021. Shizune tracks 10 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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