#631 The Leading Tax and Accounting Bitcoin Software w/ Austin Woodward

— Austin Woodward, co-founder and CEO of TaxBit, has built a $1.3+ billion cryptocurrency tax and accounting software company in three years and just raised $130 million from IVP, Insight Partners, and Tiger Global.

— TaxBit partnered with the IRS to help the agency understand cryptocurrency as an asset class and prepare for information reporting (1099) requirements anticipated in infrastructure legislation.

— The company expanded from tax filing into real-time accounting automation, allowing financial institutions and corporations to close books in compliance with GAAP and IFRS standards without manual journal entries.

— TaxBit uses a B2B2C strategy, partnering with platforms like Uphold and BlockFi rather than pursuing direct-to-consumer sales; the company has grown with only a two-person sales team generating entirely inbound demand.

— Tax loss harvesting and forward-looking tax planning are key features—users can see real-time tax positions across assets (equities, commodities, crypto) to make strategic trades and plan ahead rather than facing surprise tax bills.

— The company is tripling headcount to 200 employees by year-end, opening offices in Seattle and the UK, and plans to expand into New York (go-to-market) and Washington D.C. (public sector) to serve consumers, enterprises, and governments globally.

— Plan taxes year-round, not at filing time. Track gains and losses in real time across all asset classes to make informed decisions about tax loss harvesting and strategic trades, rather than discovering your tax burden in April when it's too late.

— Consult a tax attorney before pursuing geography-based tax optimization (e.g., relocating to low-tax jurisdictions). Such strategies require substantial time commitment, residency, and upfront legal fees to implement correctly.

— Monitor TaxBit's product roadmap for expanded asset coverage and real-world asset integrations; the company is building accounting automation that will increasingly serve institutional and corporate crypto treasuries as regulatory clarity improves.