StarZero All shows Try the podcast clipper →

Sep 7, 2017 · 19m · top-founders

775: FinTech Founder: I'll Never Raise Capital Again!

Andy Swan · 9m spoken Nathan Latka · 7m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The Top Podcast, host Nathan Latka interviews serial fintech entrepreneur Andy Swan, who shares how his bootstrapped company Likefolio transforms Twitter sentiment into actionable consumer intelligence for hedge funds after learning key equity lessons from his acquisition by TD Ameritrade.

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 45% of the talking time here. How this is scored →

Nathan as informed peer 4.6 Guest teaching 3.0 Guest disagreement 2.0 Nathan pushing back 3.1
05100:0010:000:00–2:28 · Nathan as informed peer 0/10 Episode Preview: Andy Swan's Track Record and Likefolio Overview Introductory monologue and promotional spot by Nathan previewing the guest's background and company metrics before welcoming Andy on air.2:28–5:18 · Nathan as informed peer 5/10 MyTrade Founding, Capital Dilution, and TD Ameritrade Acquisition Nathan digs into the cap table and acquisition details of MyTrade, probing whether raising capital was an unnecessary dilution mistake and if the deal was essentially an acqui-hire.5:20–7:28 · Nathan as informed peer 4/10 Spinning Out Likefolio and Analyzing Social Purchase Intent Andy explains how Likefolio spun out of TD Ameritrade and details their Twitter sentiment analysis methodology, specifically focusing on consumer purchase intent.7:28–11:09 · Nathan as informed peer 7/10 Pricing Models, Enterprise API Contracts, and Client Secrecy Nathan repeatedly presses for client counts within the 30 to 50 target market, but Andy firmly refuses due to NDA restrictions. Nathan then challenges whether offering a cheaper tier destroys the alpha for top-tier clients, which Andy refutes by distinguishing algorithmic from fundamental trading.11:10–13:58 · Nathan as informed peer 6/10 Bootstrapping Strategy and the Dangers of Venture Capital Nathan challenges Andy by asking if choosing to bootstrap means he simply doesn't know how to spend capital on customer acquisition, prompting Andy to defend staying lean and in total control.13:58–17:04 · Nathan as informed peer 6/10 Engineering Team Structure and Sentiment Analysis Nuances Nathan presents a linguistic edge case regarding negation in sentiment analysis, and Andy transparently acknowledges the algorithm's 2-4 percent margin of error and auditing process.17:04–19:36 · Nathan as informed peer 4/10 Famous Five Questions: Routines, Influences, and Entrepreneurial Patience Nathan runs through the standard Famous Five rapid-fire questions, and Andy reflects on the necessity of patience in entrepreneurship before the closing summary.0:00–2:28 · Guest teaching 0/10 Episode Preview: Andy Swan's Track Record and Likefolio Overview Introductory monologue and promotional spot by Nathan previewing the guest's background and company metrics before welcoming Andy on air.2:28–5:18 · Guest teaching 2/10 MyTrade Founding, Capital Dilution, and TD Ameritrade Acquisition Nathan digs into the cap table and acquisition details of MyTrade, probing whether raising capital was an unnecessary dilution mistake and if the deal was essentially an acqui-hire.5:20–7:28 · Guest teaching 4/10 Spinning Out Likefolio and Analyzing Social Purchase Intent Andy explains how Likefolio spun out of TD Ameritrade and details their Twitter sentiment analysis methodology, specifically focusing on consumer purchase intent.7:28–11:09 · Guest teaching 6/10 Pricing Models, Enterprise API Contracts, and Client Secrecy Nathan repeatedly presses for client counts within the 30 to 50 target market, but Andy firmly refuses due to NDA restrictions. Nathan then challenges whether offering a cheaper tier destroys the alpha for top-tier clients, which Andy refutes by distinguishing algorithmic from fundamental trading.11:10–13:58 · Guest teaching 4/10 Bootstrapping Strategy and the Dangers of Venture Capital Nathan challenges Andy by asking if choosing to bootstrap means he simply doesn't know how to spend capital on customer acquisition, prompting Andy to defend staying lean and in total control.13:58–17:04 · Guest teaching 3/10 Engineering Team Structure and Sentiment Analysis Nuances Nathan presents a linguistic edge case regarding negation in sentiment analysis, and Andy transparently acknowledges the algorithm's 2-4 percent margin of error and auditing process.17:04–19:36 · Guest teaching 2/10 Famous Five Questions: Routines, Influences, and Entrepreneurial Patience Nathan runs through the standard Famous Five rapid-fire questions, and Andy reflects on the necessity of patience in entrepreneurship before the closing summary.0:00–2:28 · Guest disagreement 0/10 Episode Preview: Andy Swan's Track Record and Likefolio Overview Introductory monologue and promotional spot by Nathan previewing the guest's background and company metrics before welcoming Andy on air.2:28–5:18 · Guest disagreement 2/10 MyTrade Founding, Capital Dilution, and TD Ameritrade Acquisition Nathan digs into the cap table and acquisition details of MyTrade, probing whether raising capital was an unnecessary dilution mistake and if the deal was essentially an acqui-hire.5:20–7:28 · Guest disagreement 1/10 Spinning Out Likefolio and Analyzing Social Purchase Intent Andy explains how Likefolio spun out of TD Ameritrade and details their Twitter sentiment analysis methodology, specifically focusing on consumer purchase intent.7:28–11:09 · Guest disagreement 6/10 Pricing Models, Enterprise API Contracts, and Client Secrecy Nathan repeatedly presses for client counts within the 30 to 50 target market, but Andy firmly refuses due to NDA restrictions. Nathan then challenges whether offering a cheaper tier destroys the alpha for top-tier clients, which Andy refutes by distinguishing algorithmic from fundamental trading.11:10–13:58 · Guest disagreement 4/10 Bootstrapping Strategy and the Dangers of Venture Capital Nathan challenges Andy by asking if choosing to bootstrap means he simply doesn't know how to spend capital on customer acquisition, prompting Andy to defend staying lean and in total control.13:58–17:04 · Guest disagreement 1/10 Engineering Team Structure and Sentiment Analysis Nuances Nathan presents a linguistic edge case regarding negation in sentiment analysis, and Andy transparently acknowledges the algorithm's 2-4 percent margin of error and auditing process.17:04–19:36 · Guest disagreement 0/10 Famous Five Questions: Routines, Influences, and Entrepreneurial Patience Nathan runs through the standard Famous Five rapid-fire questions, and Andy reflects on the necessity of patience in entrepreneurship before the closing summary.0:00–2:28 · Nathan pushing back 0/10 Episode Preview: Andy Swan's Track Record and Likefolio Overview Introductory monologue and promotional spot by Nathan previewing the guest's background and company metrics before welcoming Andy on air.2:28–5:18 · Nathan pushing back 4/10 MyTrade Founding, Capital Dilution, and TD Ameritrade Acquisition Nathan digs into the cap table and acquisition details of MyTrade, probing whether raising capital was an unnecessary dilution mistake and if the deal was essentially an acqui-hire.5:20–7:28 · Nathan pushing back 2/10 Spinning Out Likefolio and Analyzing Social Purchase Intent Andy explains how Likefolio spun out of TD Ameritrade and details their Twitter sentiment analysis methodology, specifically focusing on consumer purchase intent.7:28–11:09 · Nathan pushing back 7/10 Pricing Models, Enterprise API Contracts, and Client Secrecy Nathan repeatedly presses for client counts within the 30 to 50 target market, but Andy firmly refuses due to NDA restrictions. Nathan then challenges whether offering a cheaper tier destroys the alpha for top-tier clients, which Andy refutes by distinguishing algorithmic from fundamental trading.11:10–13:58 · Nathan pushing back 5/10 Bootstrapping Strategy and the Dangers of Venture Capital Nathan challenges Andy by asking if choosing to bootstrap means he simply doesn't know how to spend capital on customer acquisition, prompting Andy to defend staying lean and in total control.13:58–17:04 · Nathan pushing back 3/10 Engineering Team Structure and Sentiment Analysis Nuances Nathan presents a linguistic edge case regarding negation in sentiment analysis, and Andy transparently acknowledges the algorithm's 2-4 percent margin of error and auditing process.17:04–19:36 · Nathan pushing back 1/10 Famous Five Questions: Routines, Influences, and Entrepreneurial Patience Nathan runs through the standard Famous Five rapid-fire questions, and Andy reflects on the necessity of patience in entrepreneurship before the closing summary.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 84.3% · guest 15.7%0:00 · Nathan 84.3% · guest 15.7%3:00 · Nathan 19.7% · guest 80.3%3:00 · Nathan 19.7% · guest 80.3%6:00 · Nathan 28.8% · guest 71.2%6:00 · Nathan 28.8% · guest 71.2%9:00 · Nathan 37.9% · guest 62.1%9:00 · Nathan 37.9% · guest 62.1%12:00 · Nathan 21.6% · guest 78.4%12:00 · Nathan 21.6% · guest 78.4%15:00 · Nathan 60.2% · guest 39.8%15:00 · Nathan 60.2% · guest 39.8%18:00 · Nathan 73.2% · guest 26.8%18:00 · Nathan 73.2% · guest 26.8%
Sharpest disagreement ▶ 9:38 Andy refuses to share penetration numbers

Andy flatly rejects Nathan's repeated questioning regarding specific client numbers, citing strict contractual secrecy and non-disclosure agreements with hedge funds.

 Hardest push from Nathan ▶ 10:29 Nathan presses on data value dilution

Nathan directly challenges Andy's business model, arguing that releasing cheaper tier access reduces the scarce alpha that high-paying API clients rely upon.

 Biggest teaching moment ▶ 10:41 Andy clarifies algorithmic versus fundamental data usage

Andy educates Nathan on why lower-tier subscriptions do not erode API alpha, explaining the technical distinction between quantitative algorithmic trading and fundamental long-term analysis.

 Nathan holds their own ▶ 14:53 Nathan catches an NLP sentiment classification flaw

Nathan demonstrates technical understanding of natural language processing nuances by crafting a double-meaning phrase that would cause false-negative errors in the sentiment engine.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Episode Preview: Andy Swan's Track Record and Likefolio Overview 0000 Introductory monologue and promotional spot by Nathan previewing the guest's background and company metrics before welcoming Andy on air.
MyTrade Founding, Capital Dilution, and TD Ameritrade Acquisition 5224 Nathan digs into the cap table and acquisition details of MyTrade, probing whether raising capital was an unnecessary dilution mistake and if the deal was essentially an acqui-hire.
Spinning Out Likefolio and Analyzing Social Purchase Intent 4412 Andy explains how Likefolio spun out of TD Ameritrade and details their Twitter sentiment analysis methodology, specifically focusing on consumer purchase intent.
Pricing Models, Enterprise API Contracts, and Client Secrecy 7667 Nathan repeatedly presses for client counts within the 30 to 50 target market, but Andy firmly refuses due to NDA restrictions. Nathan then challenges whether offering a cheaper tier destroys the alpha for top-tier clients, which Andy refutes by distinguishing algorithmic from fundamental trading.
Bootstrapping Strategy and the Dangers of Venture Capital 6445 Nathan challenges Andy by asking if choosing to bootstrap means he simply doesn't know how to spend capital on customer acquisition, prompting Andy to defend staying lean and in total control.
Engineering Team Structure and Sentiment Analysis Nuances 6313 Nathan presents a linguistic edge case regarding negation in sentiment analysis, and Andy transparently acknowledges the algorithm's 2-4 percent margin of error and auditing process.
Famous Five Questions: Routines, Influences, and Entrepreneurial Patience 4201 Nathan runs through the standard Famous Five rapid-fire questions, and Andy reflects on the necessity of patience in entrepreneurship before the closing summary.

Statements from this episode (6)

Disclosure
Swan: Raising capital months before acquisition caused unnecessary founder dilution
“I don't think that we ever really tapped into that money because we sold the company like three or four months after, after raising. So really we just diluted our own ownership and kind of a lesson learned there.”
Andy Swan Sep 7, 2017 ▶ 3:54
Assertion Supported
Swan: Likefolio ingests every brand-mentioning tweet via official Twitter partnership
“We have a partnership with Twitter, we take in every tweet that is mentioning a brand or product that's owned by a publicly traded company, and then”
Andy Swan Sep 7, 2017 ▶ 6:26
Assertion Not checkable as stated
Swan: Boutique hedge fund market outnumbers high-end quant funds by 10,000
“We just launched the Likefolio on demand model where we're servicing these smaller boutique type of hedge funds, and so it could turn out, because there's so many more of them, there's, you know, 10 to 13,000 of those, whereas the quantitative funds, there's m…”
Andy Swan Sep 7, 2017 ▶ 8:36
Disclosure
Swan: Likefolio client contracts strictly ban disclosing client relationships or testimonials
“In fact, what's really crazy about this climate is we can't give testimony. We can't share testimonials. We can't share usage numbers because every contract that we have with these clients is buttoned up and so secure. We're not allowed to disclose even that w…”
Andy Swan Sep 7, 2017 ▶ 9:12
Disclosure
Swan: Likefolio will never raise outside capital to preserve founder ownership
“No, we have not raised capital and don't plan on it. This is something I want to own all of.”
Andy Swan Sep 7, 2017 ▶ 11:18
Assertion Not checkable as stated
Swan: Likefolio's sentiment analysis model has a 2% to 4% error rate
“About two to four percent, depending on the company, of our sentiment where we're, we register a sentiment, positive or negative, is a miss.”
Andy Swan Sep 7, 2017 ▶ 15:08
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 2,600 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more