The Investor With Joel Palathinkal

Episode: Andrew Ackerman : Dreamit VC

Air Date: September 29, 2025
Host: Dr. Joel Palathinkal
Guest: Andrew Ackerman, Managing Director (Dreamit Urban Tech)

Episode Overview

In this candid and insightful conversation, venture investor and operator Andrew Ackerman joins Joel Palathinkal to explore his unconventional journey into venture capital (VC), lessons learned as a startup founder, and his role at Dreamit Ventures focusing on urban tech, proptech, and construction tech. The episode also dives deep into the nuances of corporate venture capital, effective founder-investor dynamics, and practical advice for aspiring VCs and founders.

Key Discussion Points & Insights

1. Andrew Ackerman’s Background and Path to Venture Capital

• Unconventional Journey: Andrew reflects on his winding path through consulting, startup founding (including a summer camp-focused tech company), family office investing, and angel investments before joining Dreamit.

  "How I got here kind of only makes sense in retrospect... three totally unrelated things." (03:52)

• Dreamit’s Evolution: Dreamit transitioned from a traditional pre-seed accelerator (think “pizza at noon, speakers at 12:00”) to sector-focused, later-stage investing, particularly in urban tech, proptech, and construction tech.

  "We went a little later stage by accelerator standards... and we went vertical." (04:12)

2. Founder Empathy as a VC “Superpower”

• Empathy vs. Sympathy: Andrew stresses the unique, practical empathy founders-turned-VCs have versus those from purely investment backgrounds. They’ve “been there”—facing payroll pressure, sacrificing salary, living with uncertainty.

  "Empathy is like, I feel exactly what you feel. Sympathy is I can imagine how you feel." (09:51)

• Insight Into Startup Urgency: He notes that corporate VCs often don’t “move at startup speed,” while founder-VCs understand when “good enough” is better than perfection, balancing intuition versus analysis.

  “At some point, you got to kind of stop and say, fuck it, it’s not done. But like it's so much better. I just got to do it right.” (10:29)

3. Lessons from Startup Days: Humility, Experimentation, and Adaptation

• Humbling Surprises: Andrew shares startup stories where unexpected product decisions—like paid 'bunk notes' for camp parents—became major revenue streams, highlighting humility and openness to experiment.

  “It turned out that [bunk notes] was our second largest line of revenue that year... I didn’t think it was gonna work. And it worked out fantastically well.” (14:16–15:00)

• Culture of A/B Testing:

  “Everything you do should be a series of tests and constructed, easy to do.” (17:47)
  “The key thing is... before you try something to ask yourself, okay, how am I gonna know if this works?” (15:59)

• Startup Economics and Exit Strategy: Practical lessons about bootstrapping, the impact (and occasional missed opportunity) of not raising or taking VC money, and the importance of scale to make an acquisition attractive.

  "Having somebody from a VC with that perspective would have helped... would have been a net positive had we had institutional money in." (24:10–26:06)

4. Deep Dive: Corporate Venture Capital (CVC)

• Corporate VC Structures & Pitfalls: Not all CVCs are alike. Andrew explains two key ways CVCs are structured (separately managed funds vs. corporate budget), influencing decision speed and process.

  “Ask [corporate VCs]: Do you have dedicated funds or are you investing off the balance sheet?” (27:32)

• Challenges with CVC: Issues can include slow decision-making, governance complications (e.g., right of first refusal scaring off other acquirers), potential confidentiality risks, and problems during distress or insider rounds.

  “They might decide they’d rather own you at that point and not give you the money. Well, a financial VC doesn’t ever want to take over the company if he can avoid it.” (33:45)

• Board Dynamics: CVCs and financial VCs have different motivations regarding exits and down rounds, which can be beneficial in balancing incentives at the board level.

  "An ideal round is some corporate, some strategic... and you get all the other stuff on the financial side." (34:58)

5. Dreamit’s Investment Model and Supporting Founders

• Target Companies: No longer traditional accelerator deals, Dreamit targets “later” early-stage companies with significant revenue—“those guys aren't going to give you 6% of their company for $100K.”

• Investor Sprints: Dreamit prepares startups intensively for focused “investor sprints”—20-minute, VC-style meetings designed to mimic real fundraising processes.

  “The idea is... I’ll take a startup through their paces... I'll sit down and... burn time... because they need to know how to manage the clock." (37:32)

• Industry Focus: Urban tech (proptech/construction), health, and secure tech, with extensive preparation and curated investor lists for targeted fundraising.

• Ongoing Support: After the sprint, Dreamit stays engaged, helping with negotiation, prospect management, and term sheet analysis, emphasizing founder-friendly, long-term support.

6. Transparency, Reputation, and Practical Founder Advice

• VC Review Sites: Mixed feelings about anonymous review sites for VCs (e.g., VCGuy.co), likening them to Yelp—skewed feedback, but can still flag caution areas or raise worthwhile questions.

  “The problem with review sites in general is they're U shaped... You get the ‘I had a horrible fucking experience’ and 'this is awesome'.” (46:41)

• Due Diligence for Founders: Advises founders to contact portfolio companies that didn’t succeed—using tools like the Wayback Machine to find “disappeared” logos—and gauge a VC’s true character based on how they treat their losers, not just winners.

  “The way a VC treats the companies that haven't made it is a pretty good indication of who they are.” (52:16)

Notable Quotes & Memorable Moments

• On Founder Empathy as a VC

  "If you’ve never done your first startup, you don’t know what it feels like to be a month or two away from not being able to make payroll." — Andrew Ackerman (09:32)

• On Experimentation

  “Everything you do should be a series of tests and constructed, easy to do.” — Andrew Ackerman (17:47)

• On Advice for Aspiring VCs

  “The earlier you get, the less important the right price is and the more important ‘will it work?’ becomes to the ultimate extreme... The real question you had to answer is, is this thing going to work?” (56:24)

Timestamps for Key Segments

| Time | Segment / Topic | |-----------|---------------------------------------------------------------------------------------| | 02:34 | Andrew’s career journey and path to Dreamit | | 06:50 | How being a founder translates to VC—empathy, lessons, superpowers | | 09:32 | Founder empathy and the real pressures of being a founder | | 14:14–15:00 | Startup anecdotes: Launching revenue streams via unexpected experiments | | 17:04 | The importance of testing everything | | 24:10 | Impact of not taking outside investment on startup trajectory | | 26:26 | Deep dive into corporate venture capital structures, advice for founders | | 31:41–34:58 | Boardroom dynamics: how CVC and financial VCs impact founder decisions | | 35:15 | Dreamit’s model: investor sprints and scaling fundraising | | 46:41 | Review sites for VCs: pros and cons | | 52:16 | Founders’ due diligence: talking to failed portfolio companies | | 55:04 | Andrew’s advice for aspiring VCs: “Will it work?” vs. “What’s the right price?” |

Practical Nuggets & Takeaways

• Empathy for Founders: The lived experience of founding a startup creates a different kind of empathy and makes for better, more supportive investors.
• Test Everything: Treat product development, sales, and operations as an iterative process; humility is necessary.
• Do Due Diligence—Both Directions: Founders should vet VCs as deeply as VCs vet them, including speaking to founders of failed companies.
• CVCs Are Not Created Equal: Always ask about fund structure, approval processes, and terms before taking money.
• For Aspiring VCs: Early stage investing is about predictive judgment and identifying “what will work,” not just financial modeling.

Final Advice

“If you’re coming from a financial services background, want to get into VC, the easier path... is later stage VC, because that’s still pretty heavy on the valuation tool set. But... especially if you want to go all the way to the earliest stage, you almost got to put away all your modeling skills... and start thinking about how do I systematically answer the question, will it work?” — Andrew Ackerman (56:24)

Episode Tone: Conversational, practical, unvarnished, humorous, and rich with real-world lessons for insiders and newcomers alike.