HowardKaplan

This is what happens when psychological safety collapses. The brain shifts from collaborate mode to defend mode. Every interaction becomes a referendum on your value.

Most founder anxiety comes from living in a future that doesn’t exist yet. The customer isn’t lost. The round hasn’t failed. The company isn’t dead. Come back to today. Execute. The Next Right Thing

🚨We’re EXTENDING the deadline to join the ReThink Citizens Innovator Academy! 🎉 After lots of interest in the past week—and knowing that many of you are still working on your applications—we’ve extended the application period by one week! APPLY NOW: tinyurl.com/rcinnovators

I think about this stat at least once a week.

1 - As you raise bigger funds, VC investors make soooo much money regardless of how they do And since it can take a decade before anyone realizes how good you actually are, you can leverage the hype cycle to get phenomenally wealthy without driving real performance

Join for free: a virtual conf with 1000+ LPs, Family Offices, Funds of Funds, & GPs of VC, PE, RE, & Hedge Funds – Nov 26 on Zoom. $100M+ & $1B+ Single FOs, LPs, FoFs & other investment firms have confirmed their participation. Like & reply "+" to get the invite in DM (we're at 1200+ regs now). Our previous event attracted attendees with a combined AUM of $1.6 trillion, including: 270 Single Family Offices, 90 Multi Family Offices, 180 Funds of Funds, 300 LPs, 570 angels, & hundreds of GPs. For the first time, we're adding a virtual Private Networking Lounge with LPs, FoFs & FOs in addition to speakers' Zoom panels & presentations (US, EU, & UAE): 1) $1B+ Family Office panel: In what and how are we investing? RE, PE, VC & other alternatives – Shubhra Jain @ Tarsadia SFO ($2B); Neetu Puranikmath @ Cooper Family Office. 2) 2x+ DPI Club: How to return your LPs more than expected? – Justin Stebbins @ Northgate Capital ($5B); Douglas Mellinger @ Clarion Capital Partners ($1.8B) 3) Family Office Trends 2025 – Uli Maybach @ Maybach Foundation; Christian D Evans @ Pax Fortis Multi-Family Office. Moderated by Valerie Bertele @ Yellow Rocks. 4) 1st-generation UHNWI strategies: 1. Launch a SFO, or 2. Join a Multi-Family Office, or 3. Other ways to preserve & grow capital? – Shane Neman @ SFO / Neman Ventures; Lisa Morris @ AKS Single Family Office. 5) How to Grow AUM of a Fund in 2025: Best Fundraising Practices for PE, VC, RE, & Hedge Funds – David Butler @ Argosy Real Estate Partners ($3.6B); Jaclyn Baumgarten @ IDC Ventures ($650M AUM, IDC Network $2.5B); Ed H. @ Arena LP ($3.4B). 6) Why FoFs exist, and why LPs accept double-layer fees? – Chuck Tedeschi @ Top Tier Capital Partners ($8B); Scott Sherman @ Mesa Lane Capital Partners. 7) How to harness AI for sourcing, evaluation, and reporting? – Logan Allin @ Fin Capital. 8) How Governments Can Attract Capital, Innovations & Talent by Focusing on Venture Studios? – Preslav Panayotov @ VentureWaves Innovation Network 9) State of Venture Q3 2024 – Benjamin Lawrence @ CB Insights. 10) $2T growing Private Credit Market & what it means for Private Credit Secondaries – Brett Hickey @ StarMountain Capital ($4B+). 11) Collaboration between Family Offices, Venture Studios, VC Funds, & Corporations – Ahmed Nasser Al Nowais @ Annex Investments; Daniela Plattner @ Palm Venture Studios; Marc Wesselink @ venturerock. 12) What do our private banking clients want to invest in? Our portfolio construction – Orley J. Pacheco @ Wells Fargo ($2T) @margauxmaccoll @ @TechCrunch, @SaacksAttack @ @BusinessInsider, Abby Schultz @ @barronsonline, @theMetz will moderate some of the panels More speakers/moderators on the website.

Does your pre-seed startup need a financial model? I think yes. A lightweight model showing the main cost/revenue drivers, key KPI assumptions, cash flows, and 2-3 scenarios. That's it. Don't do it for investors, do it for yourself.

The old narrative that founders need to pitch 50+ VCs to get a term sheet is stupid. The truth is there's a small world of VCs who will actually be a great fit. Spend your time finding those perfect fit investors, instead of wasting your time spraying and praying.

These kinds of investor updates make me so angry. "Our revenue is still $0... so we've agreed a more aggressive hiring plan with [our lead VC] which will mean that we will be around 15 people by Feb next year." Why do VCs push pre-PMF startups to do this? 🤬

To all the entrepreneurs out there wrestling with conviction and doubt, this one’s for you. I see you, I feel you, and I salute you.

Founder with a "super hot round" a year back. I asked where it went wrong - "we listened too much!" @ founders: No VC has the intuition of your customers; they don't spend as many waking hours talking with your customers as much as you do. The best thing you can do is speak with customers, be introspective, and listen to your intuition. Bias for action 🖤 VC frameworks do not translate 1:1s to your company; they only translate 1:1 to other VC blogs that copy them. If they did translate successfully to your company, the VCs should be running it instead. Much too often, investors and portfolio staff expect a founder to immediately do something because they said so. But remember founders, when you signed your term sheet, you didn't sign an employment contract to report to this VC and their support staff, to be your BigCo manager. It's ok to ask for data points and reason from first principles if this is something useful to you vs follow the orders. Better than that, you can dilligence them before you sign the termsheet to see if you're actually getting a BigCo manager in investor's clothing.

Just met another founder whose company almost died because they were led along by a “lead VC” who hadn’t actually closed their fund. Turned out they were just looking for logos to show potential LPs their deal flow. There’s a special place in hell for these assh*les. 🤬

Early-stage product development isn’t about having the perfect idea—it’s about spotting an insight others miss. Often the best products come from seeing a simple truth, then relentlessly building around that core opportunity. The “ah ha moment” is the problem, not the solution.

1. It's all about the People. Easy to say, Hard to practice. But ideas truly are a dime a dozen and it's all in the execution. Invest in the smartest, most inspiring people you know and you'll do well.

Wisdom for founding teams is "talk to users". Over the last 10 years this has become the playbook for doing 0 to 1 work. As the advice became dogma, some founders forgot why it exists, and a new failure mode emerged: "the blind walk to product-market fit". YC popularized "talk to users" in response to the classic mistake of coming up with some idea in isolation, building in secret for months or years, and launching just to learn no one cares. Talking to users forces faster contact with reality. Your initial idea and and intuition are likely wrong in material ways, so you want to shrink the time to learn this. At Zapier, I tell teams to try and model this behavior: ship in the AM, demo to users in the PM. If you do this, you get 5-7 hits on reality per week compared to a team on a 2-week release process (or worse). This all makes sense and many founders conclude their idea, intuition, or experience don't really matter. They model finding pmf as y=mx+b where cycle time is "m" and the initial idea is "b". In this model, founder intuition gives them an initial head start but impact is quickly overtaken by iteration speed. This leads them to heavily discount or even outright ignore their own experience and intuition -- many get stuck doing a fast cycle, but ultimately directionless, traversal through the pmf maze. The modeling mistake here is the "m" term is decomposed into (iteration speed) * (intuition). Every time you make contact with reality, you learn something new. And you get to decide what to do with that new information. Should you ignore it? Update but carry on? Change directions entirely? This is why intuition is important. Your idea and experience do not just establish initial position on the Y-axis. They are a multiplier on every decision or change you make. The faster your iteration speed, the more overall impact your experience can have. If you're ideas are right, they are right faster. If they are wrong, they are wrong more obviously. All other things equal, founders with experience in a domain outperform blank-slate founders doing the blind walk.

In the world of startups, the most potent weapon at your disposal is not your technology or your capital, but your mindset. Begin with the unshakeable belief that you can learn & adapt to any challenge. This journey will test you, not to show your weaknesses, but to discover your strengths. Be careful listening to experts (even me) too closely — especially if they're not speaking from lived experience, but even if they are. Your journey will be different from mine.

Any founders interested in pitching a Family Office in my network? They are industry agnostic and actively write checks at the Pre-Seed and Seed stage. I'd be happy to get you connected.

I’m happy to accept the invitation to pitch at the Entrepreneurs Roundtable Accelerator investor/entrepreneurs event in Times Square on Tuesday, August 6th. Entrepreneurs Roundtable is a monthly event series that connects entrepreneurs and investors in New York City. If you’re in NYC, register at the link below to join this invite-only event! lu.ma/4oisxiae Excited to share my Quick Cart Africa Inc. journey and make new connections. Featured speaker; Naomi Goez - Forum Ventures #FinTech #Microcredit #EmergingMarkets