Ocrolus raises $24 million to scan financial documents with computer vision

Ocrolus, a New York startup that taps AI and machine learning to parse financial documents, today announced it has raised $24 million in a series B round led by venture growth equity firm Oak HC/FT. Ocrolus cofounder and CEO Sam Bobley said the fresh capital, which follows a $4 million series A in April 2018 and brings the company’s total raised to about $30 million, will fuel expansion into verticals like consumer and auto lending and advance development of the company’s underwriting solutions for banks.

Read the full article on Venturebeat here

Portfolio Spotlight: Ocrolus

We are very excited to announce the closing of Ocrolus’s $24 million Series B financing led by Oak HC/FT with follow-on support by Laconia, Bullpen Capital,  QED Investors, ValueStream Ventures, and Differential Ventures. We were introduced to Ocrolus in the summer of 2017 by Nick Adams of Differential Ventures. Ocrolus is a New York City-based fintech infrastructure platform that automates the analysis of digital documents and financial data. By eliminating manual review, Ocrolus empowers companies to reinvest their human capital and automate processes with industry-leading speed and accuracy. Ocrolus services hundreds of customers in the financial sector and analyzes millions of transactions every day with 99+% accuracy. 

The company was in our sweet spot from the moment we met their CEO, Sam Bobley. It had been seed funded primarily by friends and family, allowing Sam to build a strong founding team with a product solving a large TAM manual workflow problem. When Sam first sat down with us, he was looking to raise $750K. His pitch was very compelling about digitizing what heretofore was a high pain point manual workflow: the processing of financial services applications.  Ocrolus was a big idea and it quickly became apparent to us that a much larger capital raise was needed.  

Sam and Vik were very responsive and transparent throughout the due diligence process. Diving into everything from the company's financing history to their plans for improving unit economics to even introducing us to Sam's father, an entrepreneur himself & a trusted advisor to Ocrolus, we felt we were building a true partnership with the team. Our collaborative inclinations have few boundaries!

Sam had raised a fair amount of seed capital, so his cap table had unusual complexity to it. We rolled up our sleeves, sifted through the company's finances, and came up with a structure that would permit increasing the initial $750K Sam sought to a proposed $3M-$4M round. Indeed, over the next few months, a first class group of syndication partners concluded Ocrolus’s $4M financing in January of last year. 

It was then off to the races. Ocrolus’s rapid year-to-year revenue growth has been sensational.  Sam, Vik, and the team have built a product that checks all of the boxes: strong market fit, sound tech, tremendous scalability. They are also amongst the most intense and driven leaders we have encountered. They actively solicit and listen to all of their investors and then are quickly decisive once the facts and opinions have been satisfactorily gathered. They are also very loyal, always making sure their investors and employees are respected in any decision being made. 

Sam and Vik embody the Laconia DNA. Congratulations to them and their entire team!

For more details, see their feature in Venturebeat.

Laconia Turns Four!

We were once told that 1 year in the early stage startup world is like 20 years in human years -- if that is true, then we are celebrating our 80th birthday. At 80, we decided it was time for a face lift.

Let’s back up…

Four years ago, David and I started Laconia to better support the next generation of entrepreneurs by taking the best practices of angel investing and the best practices of institutional venture capital to build the fund we always wanted to have as founders. We wanted to leverage our operational experience and our network to build an ecosystem that provides entrepreneurs with value and guidance beyond cash investment.  

Transparency. Community. Collaboration.

These were the core values that we built our vision on, and they continue to be the backbone of Laconia today.

From our open-door policy for mentor meetings to our first full-day venture symposium for 20+ family offices and our intensive, year-round paid internship program, education has been fundamental to increasing transparency across our sliver of the venture ecosystem.

Laconia is a family. Everyone, whether an entrepreneur, a Limited Partner, or a VC co-investor, plays an integral role in the success of our portfolio companies. As we build infrastructure around sales acceleration, operational execution, and capital strategy, we continue to proactively engage our whole community. Our north star, as always, is to support founders as they embark on the most difficult of journeys - entrepreneurship.

As our vision evolves, we realized it made sense to give our company a makeover that fully reflects our core DNA, starting with our logo:

Group 5.png

We set out to not only change the top coat of paint but better communicate the foundational elements that embody Laconia - community, collaboration, connectedness, support and guidance.


Perhaps most significantly, we’ve revamped our website to further increase our accessibility through a pitch submission form, an open rolling intern application, and better organized resources.

Beyond the logo, website, and brand identity, we are launching a number of new initiatives, including a forum for founders to meet and discuss business challenges alongside fellow VCs, content series that further demystify venture and entrepreneurship, and curated community events.

When we started Laconia, it was just David and me in a room. As a full team of six, we can’t wait to see what the next chapter holds.

Thank you to Daniel Stankus for patiently understanding and capturing who we are, Adam Price & the Homer Logistics team for sharing your in-house genius with us, Bani Singh and Jake Quan for the heavy lifting on the website, Dessy Levinson for the thoughtful early support, Alex Sherman for calling our baby ugly and pushing us to prioritize this project and the team at ListenFirst for being the best officemates we could ask for since day one.

Founder Resources

Since starting our Mentor Meetings program two years ago, we’ve met hundreds of founders at various stages of their growth trajectory who have unanswered questions about how to raise capital, scale their organizations, and beyond. Through these meetings, we’ve found some key themes repeat consistently. Keeping in mind that founders always know their businesses best and that all advice should be taken with a grain of salt, we’ve put together a list of resources on best practices for key functional areas. We look forward to building upon this resource pool over time. Please let us know if we’re missing one of your must-reads!


Everything You Need To Know About Angel Investors by Denise Stephan (Crunchbase)

“They may invest as early as when a business is merely a concept, or after the company has proven to have some traction.”

How to Design a Pitch Deck: Lessons from a Seasoned Founder by Daniel Eckler (Mylo)

“Successful startups are known for their disruptive approach, so it’s interesting to see how so many innovative companies are surprisingly conservative (and sometimes sloppy) when it comes to their pitch deck .”

How Much Should You Raise in Your VC Round? And What is a VC Looking at in Your Model? By Mark Suster (Upfront Ventures)

“There are many things a VC is looking for in reviewing your business plan but beyond things the like the quality of revenue, margins, OPEX and CAPEX there’s a really simple rule I call, ‘Cash In, Cash Out, Milestones Achieved.’”

How to Raise a Seed Round by Geoff Ralston (Y Combinator)

“This brief guide is a summary of what startup founders need to know about raising the seed funds critical to getting their company off the ground.”

9 Seed Funding Gotchas by Alex Iskold (2048 Ventures)

“So how do you actually win this and get funding? Two things – preparation and traction.”

The Hackers Guide to Startup Fundraising by Fletcher Richman (Galvanized)

“I’ll walk you through my process to remove repetition and get you in more meetings with investors.”

The Top 3 Things Investors Are Looking for in SaaS Startups by Cristoph Janz (Point Nine Capital)

“Good revenue growth is worthless if the company gets huge adoption initially but doesn’t drive fundamental change.”

7 Tips for Raising Capital in a Slower Market by Alex Iskold (2048 Ventures)

“Even when capital is readily available, fundraising is still not easy.”

To Raise a Venture Round These Days, You Need To Be a Little Crazy by Hunter Walk (Homebrew)

“If your numbers are solid but not CRAZY, you definitely need a CRAZY vision.”

8 Things That Make Investors Cringe by Lili Balford (Ateliers Advisors)

“Have you ever left a pitch and wondered what investors really thought about you? I decided to roll up my sleeves and conduct a nationwide, sector and stage agnostic survey of investors.”

Why Maximizing Your Valuation May be Minimizing Your Chance for Success by Micah Baldwin (Madrona Venture Group)

“There are two schools in setting initial valuation: Maximize and Optimize.”

A Question About Risk That Founders Forget to Ask VCs by Hunter Walk (Homebrew)

“Potentially the best founder <> fund matches come when both parties are clear about what needs to still be proven out”


Optimize Your Funnel By Getting Inside Your Buyer’s Head by David Skok (Matrix Partners)

I discuss how to design a great sales process, analyze the buyers’ journey, and shorten the time to customer conversion from trials, freemium and open source products

Clarity of Message: Why You Need A Great Message & How To Create It by David Skok, Mike Troiano (Matrix Partners)

“This post focuses on how to get messaging and positioning right in the early stages of your company.”

SaaS Sales Compensation: How to Design the Right Plan by David Skok (Matrix Partners)

“In this blog post we will explore how to design sales compensation plans that help drive the right behaviors.”

Everything You Need to Know About Buyer Personas by Patrick Campbell (Profitwell)

“Quantified buyer personas are rich with data to help you make important pricing and marketing strategy decisions.”

7 “Easy” Ways to Increase Sales by Jason Lemkin (SaaStr)

“Stop acting “cheaper,''cuter, ''hipper.” Act more enterprise.”

How to choose the right SaaS sales model for my SaaS company by Sona Hovhannisyan (incredo)

“Choosing the right model can set your business in the success path and choosing the wrong model can leave your SaaS company with nothing.”


Things You Must Know to Start A Business by Bill Green (Crunchbase)

“...building a startup is a game of endurance. It doesn’t happen overnight. The first 12-18 months come with a brutal learning curve most new founders struggle to make it through.”

Diversity & Inclusion at Early Stage Startups by Kat Manalac (Y Combinator)

“Diversity and inclusion initiatives can improve culture and reduce turnover (if done right).”

Diversity at Startups by Homebrew

“A company with people from different backgrounds, ages, genders, and perspectives can spark innovation. Innovation can lead to success.”

Managing Your Startup Board — A Short Presentation by Mark Suster (Upfront Ventures)

“Boards are organizations that need managing just as you would do for your management team.”

6 Ways Great Companies Use Board Decks to Their Advantage by Max Heald (Union Square Ventures)

“I quickly found out that there is no one standard board deck for a USV company (and in fact, we’re proud of that), but I did observe a few commonalities among the most effective decks.”

Front’s Mathilde Collin on Why Discipline Is More Important Than Vision, The Right Way To Approach Investor Updates and Director Reports & How To Effectively Structure 1-1s by Harry Stebbings, Mathilde Collin (The Twenty Minute VC)

“Success will happen only if you’re consistent.”

The 5 Step Process to Perfecting Your Product Launch Strategy by Patrick Campbell (Profitwell)

“It's critical to design a process that allows you to launch vastly different product experiences within specific communities so your product can reach critical mass.”


16 Metrics You Must Keep an Eye On by Marc Andreessen

“Good metrics aren’t about raising money from VCs — they’re about running the business in a way where founders know how and why certain things are working (or not and can address or adjust accordingly.”

3 Metrics That Really Matter for Your Startup by The Muse

“While each start-up has its own unique metrics that are important, here are three categories that are almost universal.”

The Key Drivers for SaaS Success by David Skok (Matrix Partners)

“This slide deck offers a comprehensive and detailed look at the key metrics that are needed to understand and optimize a SaaS business, and how these can be used to drive SaaS success.”

What Does it Take to Raise Capital in SaaS in 2018? by Cristoph Janz (Point Nine Ventures)

“I thought about the question of ‘what does it take to raise capital in SaaS in 2016?’ and tried to give an answer that would fit on the proverbial back of a napkin..Now it’s time for the 2018 version.”

The Marketplace Funding Napkin 2018 by Julia Morrongiello (Point Nine Ventures)

“So what does it take to raise capital as a marketplace startup in 2018?”


12 Tactics to Perfect your Interviewing Process by Dana Stalder (Matrix Partners)

“When it comes to effective, data-driven interviewing, it all starts with knowing who you are and what you want — and then taking a structured approach to find candidates that meet your criteria.”

Things Learned Hiring Replacement Co-op by Nicholas Parente (Underscore VC)

“I went back, reviewed my notes, and distilled 5 key takeaways that I learned while hiring my replacement at Underscore.”

How to Know if a Key Hire is an A or a B (or even a C) by Jason Lemkin (SaaStr)

“The biggest mistake you are probably going in your first year or two to make is hiring B or even C players for key director and VP positions.”

Be Careful Hiring CEOs, Architects, Game Devs, or Dualies by Jason Lemkin (SaaStr)

“I’ve learned again and again, including quite recently, there are 4 types of hires to just avoid”

How To Get Better at Recruiting. (We All Need To) by Jason Lemkin (SaaStr)

“Recruiting is tough. I certainly don’t do it well enough. But to be a great CEO, you need to find a way to force yourself to be a great recruiter.”

Ask a Female Engineer: Interviewing + Company Culture by Cadran Cowansage (Y Combinator)

“We’ve recruited a group of female engineers with years of industry experience to try an experiment with us called “Ask A Female Engineer.”

How To Alter Your Hiring Practices To Increase Diversity by Maynard Webb (Forbes)

“If you build a culture where fit means people who expand who we are, then diversity will be germane to your future success.”

The Close: New Rules for Hiring Executive Candidates by Dana Stalder (Matrix Partners)

“The close is a critical part of a successful recruiting process”


500 startups

Andreessen Horowitz

Christopher Janz

Elizabeth Yin

First Round Review

Fred Wilson

Jason Lemkin

Mahesh Vellanki

Mark Suster

Matt Turck

Paul Graham

The Twenty Minute VC

Tomas Tunguz


Y Combinator

Content Raven Adds Instant Integration for Dropbox Customers for Secure File Sharing in the Cloud

Content Raven, a leading cloud-based file distribution toolkit that adds content control, security and deep analytics to files, today announced the addition of Dropbox™ to its growing list of storage and file sharing vendor integrations. As of today, both Dropbox and Dropbox for Business™ customers can address the innate security issues that come with sharing through the cloud-based storage platform by instantly and seamlessly adding protection, control and analytical tracking of all common file types, including images, videos and PDFs shared through the Dropbox platform.

Read full article here