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Nov 29, 2023 · 16m · founders-journal

How To Raise Capital Successfully with Dan Siroker

Dan Siroker · 10m spoken Alex Lieberman · 4m spoken
0:00 / 0:00

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In this episode of Founder's Journal, Alex Lieberman interviews serial entrepreneur Dan Siroker on his unconventional strategy of raising a $15 million Series A for Rewind entirely in public on Twitter. Siroker breaks down his viral pitch deck mechanics, rigorous back-channel investor vetting techniques, and foundational principles for managing high valuations and long-term venture partnerships.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 32.1% of the talking time here. How this is scored →

Alex as informed peer 3.2 Guest teaching 4.2 Guest disagreement 1.0 Alex pushing back 0.6
05100:0010:001:20–3:35 · Alex as informed peer 2/10 Raising Series A in Public on Twitter Alex prompts Dan to share the story behind his viral Twitter fundraise. Dan explains the transparency motivation, the influx of offers, and selecting NEA based on fund life alignment.3:36–5:51 · Alex as informed peer 3/10 Vetting Investors and Conducting Back-Channel References Alex asks how Dan vetted investors and filtered for alignment. Dan explains how his priorities evolved from early-career mentorship to values alignment and the necessity of cold back-channeling founders.5:52–10:08 · Alex as informed peer 3/10 The Ultimate Back-Channel Reference Question Dan shares his signature reference check question about why a deal would hypothetically fail in six months. Alex seeks clarification on the framing, and Dan elaborates on core fundraising principles.10:11–13:43 · Alex as informed peer 3/10 Why Founders Should Consider Public Fundraising Dan compares public fundraising to online dating versus going to a local bar, arguing that fear of copycats is overblown. He lays out a hierarchy of needs for founder-investor relationships.13:44–16:15 · Alex as informed peer 5/10 Navigating High Valuations and Managing Runway Alex points out the extreme 466x revenue multiple and presses on the valuation risks. Dan counters VC warnings by pointing to the market distribution curve and Rewind's six-year runway buffer.1:20–3:35 · Guest teaching 3/10 Raising Series A in Public on Twitter Alex prompts Dan to share the story behind his viral Twitter fundraise. Dan explains the transparency motivation, the influx of offers, and selecting NEA based on fund life alignment.3:36–5:51 · Guest teaching 4/10 Vetting Investors and Conducting Back-Channel References Alex asks how Dan vetted investors and filtered for alignment. Dan explains how his priorities evolved from early-career mentorship to values alignment and the necessity of cold back-channeling founders.5:52–10:08 · Guest teaching 5/10 The Ultimate Back-Channel Reference Question Dan shares his signature reference check question about why a deal would hypothetically fail in six months. Alex seeks clarification on the framing, and Dan elaborates on core fundraising principles.10:11–13:43 · Guest teaching 4/10 Why Founders Should Consider Public Fundraising Dan compares public fundraising to online dating versus going to a local bar, arguing that fear of copycats is overblown. He lays out a hierarchy of needs for founder-investor relationships.13:44–16:15 · Guest teaching 5/10 Navigating High Valuations and Managing Runway Alex points out the extreme 466x revenue multiple and presses on the valuation risks. Dan counters VC warnings by pointing to the market distribution curve and Rewind's six-year runway buffer.1:20–3:35 · Guest disagreement 0/10 Raising Series A in Public on Twitter Alex prompts Dan to share the story behind his viral Twitter fundraise. Dan explains the transparency motivation, the influx of offers, and selecting NEA based on fund life alignment.3:36–5:51 · Guest disagreement 1/10 Vetting Investors and Conducting Back-Channel References Alex asks how Dan vetted investors and filtered for alignment. Dan explains how his priorities evolved from early-career mentorship to values alignment and the necessity of cold back-channeling founders.5:52–10:08 · Guest disagreement 1/10 The Ultimate Back-Channel Reference Question Dan shares his signature reference check question about why a deal would hypothetically fail in six months. Alex seeks clarification on the framing, and Dan elaborates on core fundraising principles.10:11–13:43 · Guest disagreement 1/10 Why Founders Should Consider Public Fundraising Dan compares public fundraising to online dating versus going to a local bar, arguing that fear of copycats is overblown. He lays out a hierarchy of needs for founder-investor relationships.13:44–16:15 · Guest disagreement 2/10 Navigating High Valuations and Managing Runway Alex points out the extreme 466x revenue multiple and presses on the valuation risks. Dan counters VC warnings by pointing to the market distribution curve and Rewind's six-year runway buffer.1:20–3:35 · Alex pushing back 0/10 Raising Series A in Public on Twitter Alex prompts Dan to share the story behind his viral Twitter fundraise. Dan explains the transparency motivation, the influx of offers, and selecting NEA based on fund life alignment.3:36–5:51 · Alex pushing back 0/10 Vetting Investors and Conducting Back-Channel References Alex asks how Dan vetted investors and filtered for alignment. Dan explains how his priorities evolved from early-career mentorship to values alignment and the necessity of cold back-channeling founders.5:52–10:08 · Alex pushing back 1/10 The Ultimate Back-Channel Reference Question Dan shares his signature reference check question about why a deal would hypothetically fail in six months. Alex seeks clarification on the framing, and Dan elaborates on core fundraising principles.10:11–13:43 · Alex pushing back 0/10 Why Founders Should Consider Public Fundraising Dan compares public fundraising to online dating versus going to a local bar, arguing that fear of copycats is overblown. He lays out a hierarchy of needs for founder-investor relationships.13:44–16:15 · Alex pushing back 2/10 Navigating High Valuations and Managing Runway Alex points out the extreme 466x revenue multiple and presses on the valuation risks. Dan counters VC warnings by pointing to the market distribution curve and Rewind's six-year runway buffer.

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

0:00 · Alex 56% · guest 44%0:00 · Alex 56% · guest 44%3:00 · Alex 28.4% · guest 71.6%3:00 · Alex 28.4% · guest 71.6%6:00 · Alex 24.1% · guest 75.9%6:00 · Alex 24.1% · guest 75.9%9:00 · Alex 11.6% · guest 88.4%9:00 · Alex 11.6% · guest 88.4%12:00 · Alex 32.3% · guest 67.7%12:00 · Alex 32.3% · guest 67.7%15:00 · Alex 45.5% · guest 54.5%15:00 · Alex 45.5% · guest 54.5%
Sharpest disagreement ▶ 15:15 Dan refuting VC fearmongering on high valuations

Dan dismisses standard venture capital warnings about high valuations as fear tactics, arguing that having six years of runway eliminates downside risks.

 Hardest push from Alex ▶ 13:44 Alex pressing on the extreme valuation multiple

Alex highlights the steep 466x revenue multiple ($350M valuation on $750K ARR) and presses Dan on the trade-offs of raising far above standard market levels.

 Biggest teaching moment ▶ 6:03 Dan teaching his hypothetical back-channel prompt

Dan educates Alex on extracting genuine feedback from references by forcing them into a hypothetical failure scenario six months down the road.

 Alex holds their own ▶ 13:44 Alex calculating valuation multiples and market context

Alex calculates the exact multiple (466x ARR) and frames the strategic trade-offs of raising at top-of-market multiples.
the scores for every segment, with the reasoning behind each
ChapterTopicAlex as informed peerGuest teachingGuest disagreementAlex pushing backWhy
Raising Series A in Public on Twitter 2300 Alex prompts Dan to share the story behind his viral Twitter fundraise. Dan explains the transparency motivation, the influx of offers, and selecting NEA based on fund life alignment.
Vetting Investors and Conducting Back-Channel References 3410 Alex asks how Dan vetted investors and filtered for alignment. Dan explains how his priorities evolved from early-career mentorship to values alignment and the necessity of cold back-channeling founders.
The Ultimate Back-Channel Reference Question 3511 Dan shares his signature reference check question about why a deal would hypothetically fail in six months. Alex seeks clarification on the framing, and Dan elaborates on core fundraising principles.
Why Founders Should Consider Public Fundraising 3410 Dan compares public fundraising to online dating versus going to a local bar, arguing that fear of copycats is overblown. He lays out a hierarchy of needs for founder-investor relationships.
Navigating High Valuations and Managing Runway 5522 Alex points out the extreme 466x revenue multiple and presses on the valuation risks. Dan counters VC warnings by pointing to the market distribution curve and Rewind's six-year runway buffer.

Statements from this episode (10)

Assertion Not checkable as stated
Siroker: Rewind's public pitch deck got over 1,000 investment offers
“We got well over you know, we got millions of views over a thousand offers to invest, many from really great investors, and I spent the next week in meetings with folks.”
Dan Siroker Nov 29, 2023 ▶ 2:34
Assertion Partly supported
Siroker: NEA has 15-year fund lifecycles and buys at IPO
“NEA is known to have 15 year fund life cycles as opposed to the traditional 10. Very often they're buyers at the IPO. They're not sellers.”
Dan Siroker Nov 29, 2023 ▶ 3:10
Assertion Supported
Siroker: Rewind raised Series A at $350M valuation with $700K ARR
“We raised it a three hundred fifty million dollar valuation with 700 K and ARR.”
Dan Siroker Nov 29, 2023 ▶ 3:25
Insight
Siroker: Direct questions rarely reveal the truth about prospective investors
“Investors are very good at selling. So you should be careful. There's very few questions you can ask an investor that you're going to get to the core truth. Compared to talking to their references and certainly talking to back channel references are very, very…”
Dan Siroker Nov 29, 2023 ▶ 5:17
Insight
Siroker: Cold outreach to portfolio CEOs yields honest back-channel investor references
“I think founders will be really honest with other founders. So don't be afraid to, you know, you're thinking about taking a term sheet from an investor. Look at, you know, all the other people they're on the board with and just reach out to the CEOs of those c…”
Dan Siroker Nov 29, 2023 ▶ 5:30
Insight
Siroker: Asking why a partnership failed uncovers hidden reference truths
“And usually when you ask somebody their first instinct, and you ask them in this hypothetical, you get to some truth that you might not otherwise get when you ask about strengths and weaknesses.”
Dan Siroker Nov 29, 2023 ▶ 6:35
Insight
Siroker: Public fundraising reveals true market price and best matches
“And I think that's really the value of being more public in your fundraise, It helps you cast a wider net, which then you ultimately find the perfect match, the perfect marriage, and you end up, I think really getting a sense for your market prices. That's the…”
Dan Siroker Nov 29, 2023 ▶ 11:02
Insight
Siroker: Fear of copycats from public fundraising is overblown
“You know, it's true that since we did raise in public and we were successful, we've had some imitators and some copycats, but none of them really have affected us. You know, it was a little bit of like, oh, should I have Been so public about our success when I…”
Dan Siroker Nov 29, 2023 ▶ 11:24
Assertion Not checkable as stated
Siroker: Rewind received 20 funding offers at $1B valuation or higher
“We had 20 offers at a billion dollars or more but 20 out of a thousand is pretty small.”
Dan Siroker Nov 29, 2023 ▶ 14:41
Assertion Not checkable as stated
Siroker: Rewind has six years of runway to justify its valuation
“And because the good news is we have six years of runway. We've got plenty of time to live up to the big valuation.”
Dan Siroker Nov 29, 2023 ▶ 15:52
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