What I Learned Raising for AskMeEvo After iTaxi - When Your Track Record Helps (And When It Kills You)

Overview: The Serial Founder’s Paradox

Quick answer: Raising for your second company (after exit) is faster than first company — same pitch, different market. Use first company credibility: “iTaxi achieved $20M ARR, exited at $X, now attacking 10x bigger market.” Series A investors price in your operational experience. Don’t hide previous company — it’s your unfair advantage. New company needs 2-3x better metrics than first company at equivalent stage to justify redo.

When you sell your first company, investors treat you differently. The difference is supposed to be good—better access, faster meetings, higher valuations, enthusiasm. Then you start raising again. That same exit becomes an anchor. It can work for you. It can also work against you.

I’m living this with AskMeEvo right now.

This isn’t retrospective. It’s written while raising. I’m reporting what’s actually happening in the room—the mechanics of how past success shapes your next fundraise, and sometimes sabotages it. I’m testing positioning approaches. I’m sitting across from investors feeling the shift in their attention. This advice comes from real time.

The paradox is simple: Your track record opens doors. Then it sets expectations you cannot meet.

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Part 1: The iTaxi Advantage—What the Exit Actually Buys You

Let me be direct about what the exit delivered.

For related context, see European founder exit to next round, using iTaxi success, and founder process perspective.

Pattern Recognition and Investor Access

When I started fundraising for AskMeEvo, I didn’t need to explain what a Series A looks like. I didn’t need to ask “what do investors care about?” I had already lived through investor cycles, due diligence, cap tables, term sheets, the weight of managing expectations while scaling.

That experience has cash value.

Investors move faster with second-time founders. Not because we’re smarter. Because the social proof is built in. A warm intro lands differently when the person on the other end has watched you deal with a sale. The investor shifts from “Is this founder coachable?” to “This founder has pattern recognition from a prior round.” The questions change. The tone changes.

In iTaxi fundraising, I spent real energy on founder legitimacy—proving a Polish founder could build at scale, that we understood unit economics, that we could hire. With AskMeEvo, I skip that entire layer. That saves time. It saves bandwidth.

Network Reactivation

This is underrated.

iTaxi’s cap table included angels, early institutional investors, and operators who became advisors. When I started AskMeEvo, I had roughly 80-100 people who had already decided once that I could raise and deploy capital. Not all would invest again. Many would take a meeting without warm intros. Many would read the deck. Many would give honest feedback.

The reactivation rate has been 40-50%. Earlier investors have either committed, are in process, or gave meaningful guidance. That is capital efficiency. No cold outreach. No “prove you’re a real founder” conversation.

First-time founders don’t have that network yet. They start from cold intros, conference tables, credibility from product or leadership. The time difference is weeks for repeat founders. Months for founders starting cold.

Operator Credibility in Conversations

When I meet with a new investor, the conversation starts differently. The investor already knows I can hire, scale, deal with chaos. They don’t ask “can you build a team?” They ask “what team did you poach, and what aren’t they telling me?”

This is a higher bar. But it’s a different bar.

In iTaxi meetings, I spent 30% of the conversation explaining my background. In AskMeEvo meetings, I spend 5% on that. 95% on product thesis, market, execution plan. The founder credibility tax is gone. That’s worth roughly 6-8 weeks of meetings saved across a 20-week raise.

Term Sheet Velocity

Serial founders often get better terms because investors don’t need to de-risk the founder.

In first-time fundraising, investors build in protective provisions that assume the founder is learning. Board seats. Information rights. Pro-rata rights. Milestone structures. These aren’t punitive. They’re risk management.

With AskMeEvo, the first term sheet came with fewer protective provisions. Not because the investor is reckless. Because the founder risk is lower. Lower founder-risk discount means better terms. Faster closings. Less legal complexity.

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Part 2: The iTaxi Liability—When Your Exit Becomes Investor Pressure

This is the part most repeat founder content skips.

The exit is a credibility asset. It’s also a performance anchor.

The “Bigger” Expectation

Here’s what I started hearing in meetings after 4-5 conversations:

“You exited iTaxi. So with AskMeEvo, are we talking about a bigger outcome?”

Not hostile. Not unreasonable. But revealing: investors see the prior exit and assume the next company will be objectively larger. Not in absolute terms. In ambition and market size.

With iTaxi, I was attacking European ride-hailing. Real market. Venture-scale outcome. But geographically constrained, regulated, with specific customer acquisition mechanics. The TAM was billions. The serviceable market was regional.

With AskMeEvo, I’m building AI agents for knowledge work. The TAM is structurally larger. The go-to-market is less obvious. Unit economics are different. Defensibility is different.

The investor expectation is: “After ride-hailing exit for X, you should be targeting 5X or 10X.”

I wasn’t asked directly. But I felt the adjustment in the room. The investor was measuring me against an implicit valuation threshold from the first company. When my market opportunity didn’t feel obviously larger, I saw the micro-shift. Slight recalibration of attention.

This isn’t unique to me. Every repeat founder I’ve talked to mentions this. It’s the second-time burden: your last outcome becomes a floor, not a ceiling, in investor perception.

The Implied Competence Burden

With an exit on your resume, investors assume you can do everything.

They assume you can recruit elite talent. They assume you can build a go-to-market engine. They assume you can deal with investor dynamics. They assume you know how to make hard trade-offs.

The burden isn’t explicit. It lives in the diligence questions. “Walk me through how you’ll hire your leadership team.” Not sympathetic. A precision question from someone assuming you have a playbook.

The implication: you cannot use “first-time founder” as a category of mistake. You cannot say “I’m still learning how to scale.” You cannot admit gaps in operator experience without triggering recalibration.

That’s a heavier psychological load than it sounds. With iTaxi, I could say “I haven’t managed a distributed team before, let me learn.” With AskMeEvo, the same admission is read as “you managed a team before, so why don’t you know this already?”

The Comparison Trap

I notice this mostly in angel meetings.

An earlier iTaxi investor will sometimes ask mid-conversation: “So, how is AskMeEvo different from iTaxi? Bigger market? Faster to revenue?” Genuine question. Trying to calibrate risk. But the subtext is: “I backed you before and you delivered. I want to see that path again.”

That comparison is a trap because the path will never be identical. iTaxi was capital-heavy, network-driven, required geographic expansion. AskMeEvo is product-heavy, distribution-agnostic initially, focused on AI defensibility. Different playbooks. Different investor profiles. Different burn rates.

But when you have an exit, the investor instinct is to look for pattern repeat. You scaled a two-sided marketplace to liquidity. So your next company will also follow a venture growth curve.

The cognitive bias is strong. Your track record creates a template in the investor’s mind. You spend conversation time pushing back on that template.

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Part 3: The Investor Psychology Shift—From Founder to Operator to “Serial Event Risk”

The language investors use shifts.

First Time: Founder Potential

With iTaxi, the investor narrative was about founder potential. “Can this person scale? Does he have judgment to hire great people? Can he deal with ambiguity?”

The investor is evaluating upside potential because the founder hasn’t proven themselves yet. There’s romantic upside in that. Investors love backing founders who might be exceptional.

Second Time: Operator Reality

With AskMeEvo, the narrative shifts. “This founder has proven he can operate. Can he do it again, in a different market, with different unit economics and different competitive dynamics?”

It’s a more skeptical conversation. Not hostile. But the investor is pricing in founder-commodity risk. The assumption is: you can execute. The question is whether you picked a good market.

The burden transfers from “Can you build?” to “Did you pick the right thing to build?”

Third Time (implied): Serial Risk

No one talks about this openly. But I can sense it underneath some conversations.

The longest-term investors—who think in 10+ year patterns—are running a quieter filter: “Is this founder getting better at spotting opportunities, or worse?” Or more directly: “Did he get lucky once, or is he actually talented?”

The first exit creates founder credibility. It also creates a data point. If the next company underperforms relative to investor expectations, it raises the question: “Was the first exit timing, luck, or actual skill?”

I’m not facing this question directly. We’re early in the raise. But I’m hyperaware of it. Every pitch, every update, every metric is now evidence of whether I’m a repeat-exceptional founder or a repeat-average founder.

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Part 4: What Investors Ask Differently (The Due Diligence Shift)

The investor checklist changes when you’re a second-time founder.

First Time: Founder Deep Dives

With iTaxi fundraising, investor diligence on me was personal:

• Background and pattern recognition
• Hunger and motivation (are you solving a real problem or raising for status?)
• Technical judgment and hiring instinct
• Resilience under setback

All legitimate. All necessary. The focus was founder archetypal fit.

Second Time: Market and Timing Interrogation

With AskMeEvo, the investor diligence on me is lighter. But the diligence on the market is intense:

• Why are you solving this problem now?
• What changed in the macro environment that makes this addressable?
• Who else is chasing this?
• What is the risk this is premature?
• What happens if a larger company copies you?

The founder risk discount means market risk comes into sharp focus.

Investors trust me to execute. They don’t trust that I’ve predicted the market correctly. That’s a real shift. With iTaxi, investors asked “Can Lech build this?” With AskMeEvo, investors ask “Is AI agents for knowledge work a real category yet?”

Different Fears Emerge

First founder fear: Can this person actually do this? Can they hire? Can they deal with chaos?

Second founder fear: Did this person get lucky? Did market timing carry them more than skill? Are they overestimating their ability to predict the next market?

The second fear is more durable. It surfaces in questions like:

• “Walk me through your conviction on this market. What data do you have?”
• “What would have to change for you to believe this isn’t the right timing?”
• “How many other opportunities did you consider before this?”

Not gotcha questions. But different in tone and intent. First founders get asked “Can you build?” Second founders get asked “Did you see around the corner correctly?”

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Part 5: How I Positioned the iTaxi Exit in AskMeEvo Fundraising (Lessons Learned)

I’ve tested multiple positioning approaches in the first 30-40 meetings.

Positioning 1: The “Pattern Recognition” Frame (It Worked)

I started with: “I spent years in ride-hailing learning how two-sided networks scale, how to deal with regulation, how to build trust with distributed teams. Those learnings apply directly to AI agents.”

This worked. Investors responded positively because it felt like skill transfer, not template repetition. I wasn’t saying “I will build another iTaxi.” I was saying “I learned specific operational lessons that compound in this new domain.”

Key insight: Reframe the exit as a skills acquisition event, not an outcome template.

Positioning 2: The “Non-Consensus” Frame (It Backfired Mildly)

I tried: “iTaxi proved I could scale a business others thought was impossible in Poland. AskMeEvo is similar—conventional wisdom says AI agents aren’t yet viable for knowledge work. I’m betting that’s wrong.”

Investors didn’t like this. It felt like ego repetition. “I was right about the Polish market, I’m right about AI agents.” That triggered pushback.

Key insight: Don’t lean on being contrarian twice. It reads as founder stubbornness, not founder insight.

Positioning 3: The “No Longer” Frame (It Landed Best)

I shifted to: “I’m no longer hunting for a venture-scale outcome in a specific geography or category. I’m hunting for a category that compounds—where network effects or AI defensibility mean first-mover advantage is durable.”

This is closer to the truth of how I think about markets now. It repositioned the iTaxi exit as a stepping stone, not a template.

Key insight: Frame the first exit as evidence that you think in terms of category durability, not just market capture.

The Mistake I Made Early

I spent too much time defending AskMeEvo against implicit comparisons to iTaxi. “This isn’t the same market.” “Unit economics are different.” “Go-to-market timeline is different.”

Investors didn’t ask for that defense. I volunteered it, which signaled that I was anxious about comparison and unsure of my market read.

Key lesson: Let the market speak for itself. Don’t pre-emptively defend against a template your exit created.

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Part 6: Network Reactivation (How iTaxi Angels Became AskMeEvo Investors)

I’ve deliberately reactivated the iTaxi network. Here’s the mechanics.

The “Pattern Recognition” Outreach

I reached out to roughly 40 iTaxi angels and early investors with a specific frame:

“I’m starting a new company in AI agents. I’m not asking you to invest based on track record. But I would value your thinking on whether this market is real and whether my conviction holds up to scrutiny.”

That frame did two things:

1. Freed them from obligation (I explicitly said I wasn’t relying on loyalty)
2. Appealed to their investor judgment (I was asking for their expertise, not their capital)

Response rate was 35%. Of that 35%, about 60% became investors or committed to investing. So roughly 8-10 of the 40 iTaxi investors have entered AskMeEvo.

The Investor Psychology

When an iTaxi investor commits to AskMeEvo, their reasoning isn’t “I want to back this founder again.” Their reasoning is usually: “I trust this founder’s judgment. He’s betting on a specific market. That bet seems credible based on what I see.”

This is actually better than pure loyalty. It means they’re making an independent assessment, not riding on brand loyalty.

What Killed Some Reactivation Attempts

I tried reaching out to a few iTaxi investors with the frame: “I built something big once. I can do it again.”

One responded: “I don’t invest based on past outcomes. I invest based on whether I believe in this specific opportunity. Send me your deck and I will give you honest feedback.”

That was a good response. It forced me to compete on merit, not momentum.

Key lesson: Network reactivation works only when the new company makes independent sense to the investor. The exit opens the door. The new company has to walk through it.

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Part 7: The Burnout Risk (Fundraising as a Repeat Founder)

This is psychological, not structural.

Repetition Fatigue

I’ve now pitched to maybe 45-50 investor conversations. The deck has been refined 8 times. The narrative has been tested a dozen ways.

And I can feel the fatigue starting.

With iTaxi, fundraising was urgent and unfamiliar. Every meeting was proof of concept. Every investor feedback loop was data. I was learning the game.

With AskMeEvo, I know the game. I can anticipate the questions. I know what works and what doesn’t. And that knowledge is starting to feel like repetition.

The risk: Repetition creates over-confidence and pattern matching. I have a playbook now. That playbook can become a cage.

With iTaxi, I had to invent answers. With AskMeEvo, I can borrow answers. That’s efficient, but it’s dangerous. I might be answering investor questions that fit my playbook, not the questions that should be asked about this specific market.

The Expectation Weight

There’s also a psychological weight I didn’t anticipate: the weight of not failing publicly.

With iTaxi, if we had failed, it would have been a learning story. “First-time founder made mistakes and learned.” That’s the narrative of early founder failure.

With AskMeEvo, if we fail, the narrative shifts: “Serial founder backed by strong network and investor momentum built something that didn’t stick.” That’s a harsher narrative.

I’m not afraid of failure. But I’m aware that the failure story is different when you have an exit. There’s less forgiveness built in.

The Comparison Curse

Every week someone asks: “Is AskMeEvo on pace for an earlier exit than iTaxi?” Or “How does your burn compare?”

I’ve learned to depersonalize these questions. But they create low-level pressure that’s different from first-time founder pressure. It’s not “can I build?” It’s “can I build this faster, bigger, or more efficiently than last time?”

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Part 8: What I Wish I’d Known—Messaging Track Record Without Overselling

If I could go back and coach myself on communication, here’s what I’d change.

Lead with the Problem, Not the Solution Track Record

I wasted time saying “I’ve scaled two-sided networks to X GMV.” That matters, but it’s not the lead.

The lead should be: “I’ve discovered a pattern in how incentive networks form and fail. That pattern applies to the problem I’m solving now.”

Translation: Lead with pattern recognition (timeless, transferable), not outcome scale (historical, potentially limiting).

Explicitly Acknowledge What Is Different

Instead of defending differences, I should have led with: “This is structurally different from iTaxi. The go-to-market is B2B. Unit economics are per-user, not per-transaction. Defensibility is AI, not network effects.”

Stating it up front disarms the comparison. It signals confidence in the new market read.

Separate “Why Now” From “Why Me”

I conflated these for a while. I’d talk about market timing and then explain why I was the right founder.

They’re different conversations. Market timing is about the world changing. Founder fit is about your specific pattern recognition. Both matter, but keeping them separate makes both clearer.

Name the Implicit Fear

Some investors are quietly worried: “Is this founder chasing a big outcome because it’s genuinely the best market, or because the outcome needs to be bigger than the last exit?”

I now address this explicitly: “I’m not hunting for a bigger outcome. I’m hunting for a more durable outcome. That happens to be in a market that’s structurally different.”

Naming the fear defuses it.

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Part 9: The Transition—Managing Investor Expectations from “Sold iTaxi” to “Building AskMeEvo”

The mental transition investors need to make is: Stop thinking about my last exit. Start thinking about this company’s runway and metrics.

Timeline of Investor Mindset Shifts

Week 1-3 of conversations: Investors are anchored entirely on the exit. Questions are about it. Validation is through it.

Week 4-8: Investors start asking questions about the new company but with the exit as a reference point. “So your burn is X—is that efficient compared to iTaxi?”

Week 9+: Investors start evaluating the new company on its own metrics. The exit becomes historical context, not an active comparison.

I try to accelerate that transition by not mentioning the exit unless asked. If I do mention it, I frame it as “I learned X,” not “I achieved Y.”

The Specific Techniques

1. Metric-first conversations. I lead with current AskMeEvo unit economics, burn, runway, and metrics. The exit is a footnote, not the opening.

2. Future-forward positioning. “In 18 months, we will have X users and Y retention. That is the metric I care about right now, not the history.”

3. Investor selection. I’m being deliberate about which investors to activate from the iTaxi network. If an investor is primarily excited about the founder track record, not the market opportunity, I move on. That investor will be emotionally invested in the exit comparison, which creates friction.

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Part 10: What Repeat Founders Should Know

The Unvarnished Reality

1. Your exit opens doors. This is real. Use it. The 6-8 week time savings in fundraising is material. The network reactivation works. The operator credibility discount is real.

2. Your exit also creates expectations you cannot control. Investors will assume the next outcome is larger. They will measure you against the template. Understand this and plan for it.

3. The burden shifts from “Can you execute?” to “Did you pick the right market?” This is harder to control. It depends on market timing, which is partially luck.

4. Repeat founder failure is a different narrative. Not worse, necessarily. But different. It’s worth being aware of.

5. Network reactivation works only on independent merit. Your previous investors will take meetings, but they will evaluate the new company like any other. The exit saves you time, not judgment.

6. Burnout risk is real, and it’s psychological. You have a playbook now. That playbook can become a cage. Stay intentional about re-learning.

7. The repeat founder advantage is real, but it’s smaller than it appears. The time savings and network access are real. But the investor bar for this specific opportunity is still high. Don’t assume the exit carries you.

Messaging Framework for Repeat Founders

• Frame the first exit as a skills acquisition, not an outcome template
• Lead with pattern recognition, not historical scale
• Explicitly name what is different in the new market
• Separate “why now” (market timing) from “why me” (founder fit)
• Evaluate new investors on whether they’re excited about the market, not just the track record
• Transition investor mindset from the exit to the new company’s metrics

Investor Selection as a Repeat Founder

Not all investors are equally excited about second-time founders. Some get drawn in by founder track record but are secretly anxious about market timing. Those investors create friction.

I’m being deliberate about targeting investors who:

• Lead with market questions, not founder questions
• Have pattern recognition in the new category
• Are comfortable with founder-guided narrative (rather than investor-templated narrative)
• Are excited about AI and knowledge work, not just “repeat founder momentum”

This reduces the total number of potential investors. But it increases the quality of the diligence conversation and the likelihood of a clean raise.

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Part 11: Implementation Notes

For Second-Time Founders Currently Raising

1. Audit your first exit narrative. Is it helping or creating implicit comparisons? If it’s creating comparisons, dial it back. Lead with pattern recognition instead.

2. Explicitly map which prior investors have independent conviction in your market. Those are the ones to reactivate. The ones riding on brand loyalty will create friction.

3. Acknowledge the implicit question: “Is this a bigger or better outcome?” Address it directly. “I’m hunting for a more durable outcome in a market with structural defensibility.”

4. Test your response to: “What did you learn from the last exit that applies here?” This should be a 60-second answer about pattern recognition, not a 3-minute story about scale.

5. In investor meetings, spend less than 10% of the time on the exit. Spend 90% on the new market. If the investor wants more on the exit, they’re not the right investor.

For First-Time Founders (Learning From This)

1. Track your decision-making. The exits that compound are the ones where founders knew why they made the choices they made, not just that they scaled. This becomes your credibility in the next round.

2. Build a reactivatable network. Track which investors gave you honest feedback, pushed your thinking, and respected your judgment. These are the investors who will take your next company seriously on its merit.

3. Separate outcomes from skills. Your first company will exit or fail. Either way, inventory the skills you actually built. That inventory—not the outcome—carries to the next round.

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        "text": "The biggest liability is that investors assume the next company will follow the same playbook or achieve a larger outcome. They also discount founder risk, which shifts scrutiny to market timing and competitive dynamics. Repeat founders cannot use 'first-time founder mistakes' as a category of acceptable failure. The expectation is higher execution discipline."
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Internal Linking Suggestions

• Link to: “The Founder Identity Crash After Liquidity” (adjacent pillar on post-exit psychology)
• Link to: “How to Negotiate a Term Sheet Solo” (series A specific)
• Link to: “Investor Questions You Should Anticipate” (universal fundraising guide)
• Link to: “Building an Advisory Board That Actually Works” (network use for repeat founders)
• Link to: “The Difference Between Seed and Series A Investors” (audience segmentation)

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Publishing Notes

Publish URL: lechkaniuk.com/fundraising/what-i-learned-raising-askmeeevo-after-Itaxi

Distribution channels:

• LinkedIn (founder audience, personal brand angle)
• Newsletter (subscriber base, build-in-public audience)
• Syndication to platforms targeting serial entrepreneurs

Polish Translation: Yes. Title: “Co Nauczyłem Się Zbierając Fundusze dla AskMeEvo Po Wyjściu z iTaxi”

Author Note: This essay reflects real-time fundraising experience from April 2026. Some details are anonymized to respect investor relationships, but the investor psychology and positioning mechanics are drawn from direct conversation logs and pattern recognition across 40+ investor meetings.

Up Next

Frequently Asked Questions

Q: Should I lead with iTaxi success or focus on AskMeEvo’s new market?

Lead with iTaxi, then pivot to AskMeEvo. “Built iTaxi to $20M in Poland, sold it, now building AskMeEvo because I see 10x bigger market.” This frames you as proven founder attacking larger problem. Investors assume you’re smarter on second company — you’re not distracted by scaling infrastructure, you’re focused on market insight. That’s the sell.

Q: If my second company’s traction lags my first company, is that a problem?

Yes, but explainable. If iTaxi had $1M MRR at Series A, AskMeEvo probably needs $500K+ MRR at Series A (half the pace because you’re new to market). If you’re at $100K MRR, investors worry you’re not executing as well or picked worse market. Bridge that with metrics — growth rate, retention, unit economics — that beat first company.

Q: How do I price Series A for my second company?

Valuation is based on current metrics + founder pedigree. Repeat founder premium is 30-50%. If first-time founder at similar metrics would be $10M, you’re $13-15M. If you have operating evidence in new market (retention, CAC payback), valuation goes higher. Don’t anchor to first company’s Series A valuation.

Q: Does exiting first company at lower valuation hurt second company fundraising?

Somewhat, but less than you think. Investors care: did you build something valuable (yes), did you execute successfully (yes), did you get liquid (yes). The actual exit valuation matters less than the fact that there was an exit. Even a $5M exit is impressive. It proves you can take a company to exit.

Q: Should I tell second company investors if I’m disagreeing with first company’s current direction?

No. Never criticize previous company or investors publicly. If you’re on second company board, stay aligned. If you’re not, stay silent. Investors see founder drama as a negative signal about your judgment. Show respect for previous company even if you have opinions.

Second Founder Round: The fundraising process for a repeat founder’s new company. Second companies raise faster because founder credibility is established. Series A valuation for second company includes founder pedigree premium (30-50% above comparable first-time founder). Second companies need similar or higher traction than first company at equivalent stage.