Both Sides of the Table

AUGUST 11, 2021

Introducing Trust, and the Importance of Product-Founder Fit was originally published in Both Sides of the Table on Medium, where people are continuing the conversation by highlighting and responding to this story. Founders, marketers and growth leaders?—?join join the Trust waitlist here.

founder 424

founder peer-to-peer sustainability VC 424

A VC: Musings of a VC in NYC

JULY 19, 2021

It is unlikely that founders will be able to force investors out of their cap tables via the secondary markets, but a voluntary separation via the secondary market seems more likely to me. I also think startup boards need to evolve. There should be many more independent directors and many fewer investor directors on startup boards.

board 276

board finance financing sustainability 276

Dream It

FEBRUARY 1, 2022

Although it may be intimidating, you aren’t against the wall – you are at the table with everyone else. Treating Q&A as a One-Way Street Founders can take a firing squad approach to Q&A. They tend to enter a room with their backs against the wall and get blasted with questions.

VC 513

VC pitching health founder 513

Hunter Walk

APRIL 21, 2025

Soon I’ll have spent more time on cap tables than org charts. The alignment gap between investors *starts* at the Series A, meaning earlier preferred investors cannot assume their interests are always aligned with the rest of the cap table. That’s a 2025 milestone as Homebrew turns 12.5

venture capital 103

venture capital capital ventures peer-to-peer 103

Both Sides of the Table

JUNE 28, 2021

almost certainly there will be no overlap from those first three deals you thought were high quality and the 4 or 5 you’re now ready to pound your fist on the table to say you should fund.” In all likelihood 7 or 8 deals would really stand out as truly exceptional, MUST DO, slam-your-first-on-the-table type deals. But here’s the rub?—?almost

advice 301

advice angel investing venture capital investment 301

Entrepreneurs' Organization

SEPTEMBER 13, 2021

Create a table with the different collaboration modalities your team uses in the left hand column—email, phone calls, IM, collaborative spaces, etc. Then, have two other columns in this table: Norms the team wants to agree on. Spend 30-60 minutes as a team and agree on what I call an “architecture of collaboration.”

collaboration 252

collaboration peer-to-peer culture energy 252

Revolution

JUNE 30, 2025

With cost savings on the table and industries and communities suffering real knock-on effects from global warming, the business case for climate innovation has only gotten stronger. The conversation: Why climate tech isn’t just necessary; it’s investable and inevitable. The takeaways: “There’s so much talent concentrated between D.C.,

innovation 130

innovation funders disruption opportunity 130

This is going to be BIG.

MAY 2, 2025

Founders dont like to burn social capital wasting the time of their cap table, so just making sure they know that all deal flow and referrals are appreciated, and to let them know not to play VC by trying to figure out if its good or not. You dont need to go viral.

VC 195

VC pitching B2B marketing networking 195

American Entrepreneurship

JANUARY 8, 2025

Our personalities were compatible, but we brought different skill sets and perspectives to the table. Each team member should bring something unique to the table, and the teams combined efforts should create a synergy that propels the startup toward its goals.

startup 98

startup culture entrepreneurship development 98

This is going to be BIG.

MAY 13, 2019

I have a portfolio where 50% of the investments have founders that come from diverse backgrounds—and yes, I want them to get money from all of the still-active funds on Uber’s cap table that benefitted from the IPO.

culture 331

culture incumbents enablement sustainability 331

Revolution

MAY 23, 2023

From the founder’s perspective, it is a missed opportunity to bring an additional third-party investor onto the cap table who can help diversify funding sources and add strategic value. These are not hypotheticals — I have seen this play out more than once over the last five years.

real estate 278

real estate venture capital VC innovation 278

This is going to be BIG.

MARCH 18, 2019

I backed that company in 2013 when it was basically a table top science project, but the key was a series of connections that could have only been possible as a full time investor. Take the example of goTenna , a thriving communications hardware startup located in Downtown Brooklyn that employees almost 50 people.

startup ecosystem 356

startup ecosystem real estate startup economic development 356

American Entrepreneurship

JUNE 20, 2025

AI-Native Document Intelligence That Goes Beyond OCR Legacy solutions built on Optical Character Recognition (OCR) have long struggled with edge cases—whether it’s messy tables, complex forms, poor handwriting, or degraded scans.

health 95

health leadership accelerator entrepreneurship 95

Dream It

MAY 19, 2021

Better to get this out on the table so you don’t waste time with a fund that will never invest in your deal. On the other hand, maybe you and your board have confidence that the amount being raised is the minimum required to achieve key milestones and a smaller raise simply does not make sense.

pitching 393

pitching board health VC 393

A VC: Musings of a VC in NYC

AUGUST 10, 2020

Typically the only thing we all have to agree on is what the cap table will look like before and after the financing so that the correct numbers are put into the documents. Everything else is pretty standard anyway. There is this narrative that equity rounds are expensive and take a long time and that SAFE notes are quick and inexpensive.

finance 279

finance financing founder ventures 279

This is going to be BIG.

APRIL 13, 2022

I mean trusting what each one brings to the table—and being honest about the process of earning that trust and what it means to having a productive relationship. For example, if you’re a sales oriented founder that gets backed pre-launch, then an investor isn’t going to assume that founder has any product design skills.

founder 415

founder VC board strategy 415

The Seraf Compass

JANUARY 25, 2023

In Part I of this article we gave an overview of capitalization tables and the key terms used in cap table analysis that every investor must understand: Valuations, Security Types and Share Counts.

capital 290

capital 290

Entrepreneurs' Organization

SEPTEMBER 13, 2023

Educational videos, whiteboard animations, video explainers — each popular type of marketing video brings something unique to the table, and it’s critical to use the right tool at the right time to get the results you want! So, how can you determine which video is best for your strategy’s needs? Read on, and you’ll learn all about it.

education 222

education media strategy creativity 222

Entrepreneurs' Organization

MARCH 8, 2023

This would benefit not only employees but also the business, as it would bring different perspectives, ideas, and ways of thinking to the table. We need to create a culture that celebrates and supports working mothers and recognizes the unique skills and perspectives that they bring to the table.

support 245

support leadership entrepreneurs culture 245

Entrepreneurs' Organization

JANUARY 7, 2022

When you bring multiple buyers to the table in an auction-like environment, you know you’re making the best deal the market can bear. This should include steps to get your books in order, conduct a professional business valuation , seek professional legal input, and consult an M&A advisory expert to explore all options on the table.

entrepreneurs 263

entrepreneurs mentorship consulting strategy 263

This is going to be BIG.

JANUARY 24, 2022

The best boards are ones that bring a diversity of perspective to the table—and this is especially true for Web3 companies who are in the middle of a frenzied and turbulent market. Those companies were funded by the investors who participated in the prior crash, not the ones that ignored the internet entirely.

construction 259

construction board VC financing 259

Dream It

JANUARY 13, 2021

That’s something I didn’t realize when I was a founder sitting on the other side of the table. Before the call, I will try to visit your site and check out your deck, but as an associate, I talk to tons of companies and don’t always have the time to do a proper deep dive. So context is key.

VC 364

VC founder consulting networking 364

Both Sides of the Table

NOVEMBER 10, 2021

Density & the Future of Real Estate was originally published in Both Sides of the Table on Medium, where people are continuing the conversation by highlighting and responding to this story.

real estate 249

real estate investment investing venture capital 249

Entrepreneurs' Organization

DECEMBER 1, 2021

When a dismal job market upended my hopes of becoming a high school English teacher, I ventured into the food and wine industry in my home state of Colorado: I began waiting tables at a restaurant called The Med.

hospitality 268

hospitality leadership collaboration entrepreneurship 268

Entrepreneurs' Organization

JULY 1, 2022

On the other side of the table is the conference room, where we focus on business. Combining the dinner table with the conference room table is not easy, and not everyone can relate to the challenge. On the one hand, family (hopefully!) symbolizes a place of love and security.

investment 220

investment investing founder culture 220

Revolution

MAY 4, 2022

We leaned in during weekly board meetings and reinvested when others left the cap table. We aren’t the type of partner that agrees with everything and rubber stamps decisions, but our support for Convene never wavered. From day one of our partnership, we believed in Ryan’s vision.

real estate 264

real estate coworking spaces coworking hospitality 264

A VC: Musings of a VC in NYC

JANUARY 14, 2021

While Bitcoin is the gold standard in crypto, Ethereum has been the innovator, bringing new ideas, particularly smart contracts, to the table. Smart contracts allow developers to easily build things on a blockchain and we have seen a proliferation of new things built on the Ethereum blockchain as a result.

enablement 226

enablement innovation development support 226

Entrepreneurs' Organization

MAY 21, 2021

Combining the family dinner table with the conference room table comes with a slew of issues, both rewarding and challenging. . My goal is to empower other second-generation businesses to thrive while maintaining healthy family relationships. . The challenges of succession. Wasting time when you could be growing the business .

founder 286

founder financing finance investment 286

This is going to be BIG.

MARCH 14, 2021

You’re trying to figure out if someone has a “tell” that gives you an insight into their character and personality—good, bad, or otherwise, and the same is true of me for founders on the other side of the table. I feel like it’s better just to put all my cards out on the table.

media 243

media founder networking support 243

Both Sides of the Table

APRIL 6, 2020

It’s slightly harder if you’ve only done an A-round and therefore have just one VC around the table who owns more than a majority of the preferred stock. I have found VCs to work collaboratively on these to help entrepreneurs in this time of need. In this instance they would need to give up the right entirely.

VC 279

VC peer-to-peer startup advice 279

Both Sides of the Table

OCTOBER 26, 2020

Here’s What it All Means was originally published in Both Sides of the Table on Medium, where people are continuing the conversation by highlighting and responding to this story. I am truly thrilled to see what she makes of it. Kara Nortman Was Just Promoted to Co-Managing Partner at Upfront Ventures.

ventures 361

ventures leadership mentorship venture capital 361

Revolution

FEBRUARY 20, 2024

Co-founders Adrianne Nickerson, Elaine Purcell, and Joanne Schneider also bring decades of healthcare experience to the table, with backgrounds that include leading roles at Privia Health, Robin Care, CareMore Health, and Kindbody.

ventures 246

ventures investment investing health 246