Aug 27, 2020 · 27m · top-founders
Wingman Hits $6k MRR, 24 Y.O Uses to Track Option Trades
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview with Nathan Latka, 24-year-old software engineer Ben Latz discusses bootstrapping Wingman—a niche options trading tracker generating $6,000 in monthly recurring revenue—while concurrently scaling The Tie, an institutional cryptocurrency intelligence platform.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 33.8% of the talking time here. How this is scored →
Nathan as informed peer 3.1 Guest teaching 2.8 Guest disagreement 1.3 Nathan pushing back 2.9
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 14:14 Ben sets clear boundaries on revenue disclosure
Ben repeatedly declines Nathan's attempts to uncover The Tie's revenue, clarifying that he is only authorized to share Wingman metrics.
Hardest push from Nathan ▶ 22:30 Nathan refuses non-answers on acquisition mathNathan directly challenges Ben's evasion on valuation, stating he does not believe a finance guy hasn't calculated his exact walk-away price.
Biggest teaching moment ▶ 3:45 Ben breaks down options tracking versus stock trackingBen corrects Nathan's assumption that mainstream brokerages should easily provide these analytics by highlighting the complex contract dynamics of options.
Nathan holds their own ▶ 23:06 Nathan breaks down after-tax liquidation mathNathan immediately calculates cap-table distribution and after-tax cash proceeds on a $500k exit against ongoing monthly cash flows.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Preview: Wingman's Pricing and Revenue Milestone | 1 | 1 | 0 | 0 | Introductory teaser, subscriber pitch, and high-level setup of the guest's background split between Wingman and The Tie. | |
| How Wingman Simplifies Options Trading Tracking | 3 | 4 | 1 | 2 | Ben educates Nathan on why major brokerages fail at options tracking due to complex expirations and multi-leg contracts. Nathan calculates MRR and pushes on why Ben would pivot focus away from an active revenue stream. | |
| The Tie's Data Products and Real-Time Scraping | 3 | 4 | 0 | 1 | Nathan offers an oversimplified example with 'Nathan coin' to understand The Tie's sentiment analytics, and Ben validates the concept while detailing their scraping infrastructure. | |
| The Tie's Organizational Structure and Global Dev Team | 4 | 3 | 1 | 3 | Nathan pulls up Crunchbase and LinkedIn live on air to drill into SSI and clarify the co-founder versus advisor roles in the corporate structure. | |
| Monetization Strategy, SigDev Traction, and Equity Holdings | 3 | 2 | 3 | 5 | Nathan repeatedly presses for exact revenue figures for The Tie and its SigDev product, but Ben stands firm in refusing to disclose financials due to minority co-founder status. | |
| Proprietary Tech Licensing, Moats, and Strategic Alliances | 4 | 4 | 2 | 4 | Nathan challenges the moat by asking why an enterprise buyer like Coinbase wouldn't just poach the named overseas developers. Ben counters by detailing exclusivity agreements and multi-layered licensing with SMA and ROI. | |
| Bootstrapping Lifestyle, Low Burn, and Acquisition Valuation | 5 | 2 | 3 | 6 | Nathan aggressively tests Ben's financial rationales, rejecting Ben's initial refusal to name an acquisition price and walking through after-tax compounding calculations. | |
| Famous Five Questions with Ben Latz | 2 | 2 | 0 | 2 | Standard Famous Five wrap-up where Nathan checks tools, sleep, and background before delivering the recap monologue. |
Statements from this episode (13)
Latz spends one to two hours daily running Wingman as a side project
“Definitely The Tie. So that's my full-time focus, but you know, spending an hour or two a day on Wingman treating it more as a side project now that it's pretty developed.”
Brokerages give retail options traders no performance data beyond YTD P&L
“These options traders who are individuals they're given no data from their brokerage firms about their trading and their performance and analysis besides a single PNL number year to date.”
Wingman reaches 180 paying customers and 80 active free trials
“Right now there's a 180 paying customers and about 80 people on their free trial.”
Wingman generates roughly $6,000 in MRR with $49 per month pricing
“So the introductory price was 25 a month and just out of respect to people who sort of latched on early, you know, I'm happy to carry them forward. But yeah, right now it's just a 49 dollar tier or four 90 for the year. And yeah, so it's currently about 6000 M…”
The Tie leverages Twitter's firehose to calculate real-time crypto sentiment
“We're an official Twitter partner. So we leverage their fire hose and calculate real time investor sentiment on, you know, hundreds of cryptocurrencies. And we feed that we sell APIs to hedge funds and other market participants.”
Crypto tokens typically surge 20% to 30% upon a Coinbase listing
“If a coin gets listed on Coinbase, you know, it's probably going to go up to 20 or 30%.”
The Tie traded equity to SSI in exchange for discounted engineering rates
“We have sort of an in-kind arrangement where they're providing, you know, discounted rates as in exchange for some equity in the company.”
The Tie's tool drives approximately 50% of breaking news in crypto
“Currently it's driving about 50% of breaking news in crypto comes from our tool.”
The Tie generates monthly revenue well above its cash burn
“I mean, we are well above our cash burn per month.”
Latz holds less than 20% equity in The Tie after strategic partnerships
“Yeah. Yeah, and we just have, we have really strategic partners, and so that, the cap table has been divvied up among them, which allows us to access all this technology without significant development cost.”
The Tie holds exclusive crypto rights to SMA and ROI technology
“Sort of the relationships we have in place and the exclusivity deals that we have, in a sense, don't even allow any other company to access either the sentiment technology or the SIG dev technology unless they come through us. So we have exclusive access to bo…”