"Tech Finance" with Sasha Orloff

There are genuinely non-obvious facts scattered throughout - the 1994 creation of the tax payment system, 3,000 tax endpoints in North America, 12% misclassification rate, the cartel overpayment-refund laundering scheme - but these are interspersed with lengthy anecdotes, a sponsor break, a Golden Gate Bridge metaphor, and startup-narrative padding that dilutes the signal-to-noise ratio considerably.

“tax payments are not payments, they're compliance events. And that's why you cannot have a bipartite compliance level”

“12% of tax payments are ah, misclassified by the internal systems and there's humans under tax receivership trying to quickly within two weeks reassign them properly before but the taxpayer still occurs two weeks of penalty”

The reframing of tax payments as compliance events (not generic payments) and the vision of eliminating tax deadlines by spreading payments over time are genuinely fresh angles, but the episode leans heavily on recycled startup tropes - small team beats bureaucracy, Tesla vs GM, Warren Buffett 'stick to what you know,' 'never underestimate a small team' - that undercut the originality.

“I want to kill the deadline of tax season. Uh, it's so stressful. It's stupid.”

“The reason why Tesla is Tesla and General Motors did not create a Tesla is a prime example of that”

Solon Angel is a genuine domain practitioner - early AI in accounting via Mindbridge, five years at Caseware building global distribution, angel investor with LP relationships, and board roles at accounting firms - making him credibly experienced rather than a pure thought-leader circuit guest, though Remittian is still early-stage and the depth of at-scale validation is limited.

“I spent five years in CaseWare, which is the third largest provider of accounting software in the world”

“I run into a DeepMind um, in 2014 in Paris where they explained how deep reinforced learning mechanisms will allow to self adapt to repetitive video games”

The episode delivers a solid layer of concrete specifics - named client firms, real dollar figures, named regulations, and operational metrics - that ground the discussion meaningfully, though some numbers (e.g., $85B penalties) are asserted without sourcing and several claims about the upcoming partnership are deliberately kept vague.

“85 billion of late fees and penalties per year in North America. It's a tax payment network of $7 trillion in the US alone”

“we cover 300 of the 3,000 tax endpoints in North America”

The host occasionally asks productive follow-ups - pushing on the general counsel story, probing why the problem hasn't been solved, and challenging the 'AI company hiring more people' contradiction - but he defaults to affirmative filler ('I love it, I love it'), inserts a long personal anecdote about the Golden Gate Bridge that adds nothing, and rarely challenges the guest's bolder claims with meaningful scrutiny.

“Can you share a little bit more about this thing you were talking about with the general counsel where they're like, you're like no, you actually, you can do this”

“I love it, I love it”