Category Archives: Venture Capital

Angel Investing – Ringing in a New Decade

2020 in sparkling gold numbers celebrating the New Year or Christmas with glittering ornaments and decorationsThe New Year is great time for reflection, especially when entering a new decade. Looking back over the past ten years, the ecosystem of Angel Investing has experienced a number of innovations, seen new players enter the market and even added some new terms to the lexicon. A few highlights include:

  • Angel List – created in 2010 by Naval Ravikant and Babak Nivi as a deal sharing platform, Angel List now serves as a source of talent for the startup community and provides syndication opportunities within the VC community.
  • The Unicorn Club” – coined by Venture Capitalist Aileen Lee in 2013, the term unicorn refers to a privately held startup company with a value of over $1 billion. According to CB Insights, as of the end of 2019 there were more than 400 unicorns and two new categories; a decacorn (valued over $10 billion) and a hectocorn (valued over $100 billion) added to the list.
  • The Jobs Act – Signed into law in April 2012 by President Obama, The Jumpstart Our Business Startups (JOBS) Act impacted capital formation, disclosure and registration requirements and introduced Equity Crowdfunding.
  • The FPO or Final Private Offering – Investors hoping to be able to participate in the final private financing round of a company prior to an Initial Public Offering were able to pool their funds into special purpose vehicles established to enable them to participate alongside VC firms and other early backers.
  • A significant increase over the past ten years in the number of Accelerators providing mentorship, capital, introductions to investors, co-working spaces and other operational services to startups. A great resource of Accelerators and their focus in the NYC area can be found in a  list put together by 37 Angels.
  • The Rise of the Female Investor – Over the past decade, we have seen a number of new VC Funds and Investment Platforms started by women and focused on investing in women. The list includes Halogen Ventures, SoGal Ventures, Female Founders Fund, BBG Ventures, Portfolia, Golden Seeds Ventures, and Plum Alley among others.

Now it’s time to consult your crystal ball to see what this next decade will bring!


Angel Investing – Becoming an angel investor

Angel investor word cloudOver the past few months, I have had several people reach out to me to ask my advice as to how to become an angel investor. So I thought it timely to put pen to paper to provide my take as to how to consider investing in this asset class. There are obviously many approaches to exploring this question; this is just one woman’s view!

When considering becoming an angel investor, consider the following three questions:

  • How much money do you plan to allocate to this asset class?
  • How much time do you want to spend in sourcing and reviewing possible investments, mentoring entrepreneurs and getting involved in the startup eco-system?
  • What are your goals and objectives in addition to seeking a financial return?

In considering angel investing, it is important to take a portfolio approach. Failure rates for startups are quite sobering. While a bit dated, a 2007 report published by the Kauffman Foundation provides some insights into the performance of early stage companies and the importance of constructing a diversified portfolio. The amount of money you have to allocate to this sector will influence the type of angel investor you choose to become. Where you fit on the spectrum of super angel writing significant checks to individual companies to participating in a fund structure with more reasonable financial entry points will again depend on the total dollar amount you are comfortable committing. In investing in individual companies, it is important to keep in mind that follow-on investments need to be factored into the financial picture.

Investors considering investing in individual companies will often choose to join an established angel group, either in their geographic region or one that focuses on a specific sector or investment theme. A great source of angel groups is the Angel Capital Association. Once you have identified groups that may be of interest to you, check out their websites to see  their criteria for membership. What are the expectations as to the  amount of capital you are expected to invest, minimum investment per transaction, expectations regarding participating in the due diligence process, etc. Try and find a member of the angel group through network connections and reach out to them to get a better sense as to the culture of the group. Most angel groups will invite prospective members to attend a screening or review session to get a better sense as to what it might feel like to be a member.

If you plan to allocate a smaller dollar amount to this sector, you may want to think about participating in a fund structure rather than making individual investments.  Some funds will enable their investors to participate in the due diligence process or co-invest alongside the fund. Once you have determined how much of your financial resources you are willing to allocate, it is important to determine how much time you wish to allocate to angel investing. Part of answering this questions, really depends on where you are in life – if you are working full-time in a profession that requires travel, etc. it might be difficult to dedicate a significant amount of time to both sourcing and vetting early stage opportunities. Personally, I have found it very helpful to participate in Demo Days, Pitch Competitions and other activities to get a broader sense of what is happening in the startup ecosystem.

The final question I pose to prospective angels is very important – what are your goals and objectives in addition to seeking financial returns. Is there a vertical you are passionate about, be that healthcare, education… Are you looking to invest in companies having social impact or changing the gender gap that exists in early stage funding? One of the great perks of being an angel investor is that you get to decide on your own investment thesis. Therefore, it is important that you align your personal goals and objectives with those of any angel group or fund family you chose.

I have chosen to construct my early stage portfolio with a combination of individual investments and funds. Through participation in both Golden Seeds and New York Angels, I have access to many opportunities to invest directly in early stage companies while taking advantage of the vast expertise of my fellow members. I use funds as a means to both participate in sectors where I do not feel I have either significant access or expertise – two examples would be Future/Perfect Ventures ( enabling me participation in the Blockchain space) and Blossom Capital ( focused on Series A financings in the European market) as well as to focus on women founders/funders through investments in SoGal Ventures, Portfolia, and the AVG Women’s Fund. In addition, through my investments in Chestnut Street Ventures, I have the opportunity to co-invest with other Penn alums supporting Penn entrepreneurs.

Whatever path you chose to becoming an angel investor, enjoy the ride!


Angel Investing – Books, Blogs & Bootcamps

IMG_0376Although long past are the days of racing up and down the aisles of Staples, kids in tow, to acquire all the school supplies on the “list” (probably these days best achieved with a one-click of Amazon Prime), the imminent arrival of the crisp weather of fall always turns my attention to “back to school” thoughts. These days, back to school means reviewing resources to help educate angel investors. Having had the privilege over the past six years to provide leadership to the Golden Seeds Knowledge Institute, I am always on the hunt for training resources to assist both new and seasoned angel investors under the assumption that learning is a lifelong process no matter the discipline. I like to segment investor training into three categories:



Although these are many great sources of information on angel investing, a few of the favorites on my bookshelf include:

Feld & Mendelson’s Venture Deals.  Filled with rich content covering topics such as term sheets and how to raise money, this is a fabulous resource for both investors and entrepreneurs.

David Rose’s Angel Investing – The Gust Guide to Making Money & Having Fun Investing in Startups. This book is one of the most comprehensive guides to angel investing I have read incorporating a wealth of knowledge from David’s incredible history of investing in this space.

Brian Cohen’s What Every Angel Investor Wants You To Know. This is a fun read filled with both advice and anecdotes from the Chair of New York Angels for both the investor and the entrepreneur seeking early stage funding.

Alex Wilmerding’s Term Sheets and Valuations. For those of you who want to understand the intricacies of Term Sheets, this a resource and that I recommend to all investors who take my courses at Golden Seeds.

Basil Peter’s Early Exits. This book covers many topics relevant to the exit process such as exit strategy and investor/entrepreneur alignment.

Richard Lambert’s Financial Literacy for Managers. Although geared more towards public company financial analysis, this resource from Wharton Professor Richard Lambert discusses many of the concepts such as benchmarking, DCF analysis and cost analysis which are important to a startup’s financial health.

Clearly, there are many other great publications out there, these are some of my picks.


Subscribing to Blogs from experts in the field is a great way to keep yourself informed as an angel investor. Here is my list of VCs whose blogs I follow and find informative:

Mark Suster’s Both Sides of the Table.

Fred Wilson’s Daily AVC Blog

The First Round Review

Jalak Jobanputra’s The Barefoot VC

Golden Seeds Blog

Ed Zimmerman, Chair of the Tech Group at Lowenstein Sandler, provides great insight into may topics including his recent post in the WSJ regarding SAFEs – LINK


I am often asked for a recommendation for courses, either online or in-person, that address angel investing topics. Here is my current list:

Golden Seeds Knowledge Institute:  Golden Seeds developed a series of investor training modules to help our members understand the basics of angel investing. Several of these modules are open to guests.

Angel Capital Association: through it’s Knowledge Center provides a variety of seminars and workshops on various topics.

First Round Capital runs a program Angel Track – a Masterclass for Emerging Angels.

Y Combinator  and Stanford also have courses for angel investors

In addition, for women investors  37 Angels Bootcamp and Pipeline Angels  have angel investor training programs.

Please use the comment section to add Books, Blogs or Bootcamps to the list!

Angel Investing – Burn Rate & Cash Runways

Businesswoman presenting her business ideas

One of my favorite First Round Capital Holiday Videos is the the 2014 release – “It’s All About Burn Rate”  set to the tune of Meghan Trainor’s “All About That Bass”.  I sometimes find myself humming that tune when I am reviewing an investment opportunity from an entrepreneur who does not fully appreciate the importance of understanding how burn rate and cash runway can impact the success/failure of their venture. When analyzing the financial structure of an investment opportunity, I try to evaluate both the amount of time the funding will last as well as the milestones/traction that the funding will enable the company to achieve. Will the proposed funding result in:

  • Achieving cash flow “break-even” which allows the company to have some measure of control over their financial destiny?
  • An inflection point of milestones/traction that will position the company to raise another round of funding at more attractive valuation levels?
  • Landing in the “dead zone” – not enough traction to attract the next round of funding and without further funding in need of cutting expenses.


If the current raise enables the company to generate enough recurring revenue to operate on a break-even basis, then the company can continue as an operating entity without having to lay-off staff, reduce marketing outlays or frankly shut the doors and cease operation. The company needs to have a clear understanding of their variable versus fixed costs – what expenditures are mandatory to allow the company to survive versus those that can be reduced or even eliminated for a period of time. Growth may be slower than desired, but may at least provide the company the time to pivot their strategy or hold out for a more attractive funding environment.

Traction reached for next round:

For most of the companies in which I am investing, there will be multiple rounds of financing required before the company is in a position to exit. It is critical to understand what are the milestones/traction that the next investor will require and how does the company plan to achieve these milestones within the runway provided by the current raise? On the expense side, does the company have a strong grasp of the resources required to execute on the plan? Do the assumptions for revenue recognition take into account a realistic sales cycle for the product/service being offered?

The “dead-zone”:

Unfortunately, many companies end up in this position either because they do not raise sufficient capital or do not have the ability to actually execute on the plan that would position them to be attractive to the next investor. I find this oftentimes with companies that utilize convertible notes and end up within sight of the maturity date without enough demonstrated progress. As an investor, I am usually faced with the decision to extend my note, invest more in the company to provide some life support, or hope that there is at least some asset value to be distributed to note holders in the event of liquidation.

Remember as the music states – “It’s All About Burn Rate” 


Angel Investing – Twelve Days of Christmas 2017

12 days of christmas: 12 Snowflakes

On the first day of Christmas
St. Nick sent to me:
A Membership at The Wing! Continue reading

Angel Investing – Ringing in the New Year 2017

2017 Capodanno Natale 1It’s that time once again to reflect on the prior year and make some resolutions for the next. In last year’s post, I suggested that you:

  • Take a critical look back at portfolio companies that didn’t make it and try to ascertain what really went wrong.
  • Expand your access to quality deal flow
  • Become a mentor to a young entrepreneur

Here are a few of my suggested resolutions for 2017: Continue reading

Angel Investing – A Note on Notes

Business Concept: Close-up the Funding button on the keyboard and have Lime, Green color button isolate black keyboardThere are a variety of funding options for entrepreneurs to consider as they explore taking in external capital. For investors, understanding the pros and cons of these various funding options and how they fit into a company’s overall funding plan is critical. One option, a Convertible Note, is a hybrid structure that is used as a bridge to a future equity round. In addition to a stated interest rate and maturity date, Convertible Notes will have conversion terms that outline how the notes will be repaid or converted into equity. The amount of equity that a company needs to raise to trigger the conversion of the notes is referred to as the qualified equity financing. Historically, I have seen this form of funding used primarily in pre-seed rounds where the company needs to raise a small amount of capital to get to proof of concept as well as a bridge financing between a Series A and B round in order to provide the company with a bit more runway to get to the metrics required by a Series B investor. Continue reading

Angel Investing – Twelve Days of Christmas 2015

12 days of christmas: 12 Snowflakes

On the first day of Christmas
a founder shared with me:
A Term Sheet for Series B Continue reading

Angel Investing – Financial Projections – “Cash is King”

Cash is King Shopping Money Vs Credit Buy Power CurrencyAs an angel investor, I see lots of financial models, which range from the very simple to the extremely complex. I am often asked why I insist on seeing the actual model ( yes the excel not the pdf version) as it all based on layers of assumptions. In response, the financial model is nothing more than a quantitative expression of the business model and in fact what is most important to me are the assumptions that underlie the numbers. Continue reading

Angel Investing – Avoiding “Energy Vampires”

focus on solutions conceptEarlier this week, I was listening to an NPR program on “energy vampires”, those special individuals whose interactions can literally drain the energy from us.  The term “energy vampires” was coined by Dr. Judith Orloff, a clinical professor of psychiatry at UCLA in her book Positive Energy. Now everyone has had some experience with “energy vampires” – those special people who cause some of the following reactions:

  • You hope a call to them goes directly to voicemail
  • You need a trip to Starbucks before and after meeting with them
  • You would rather have a root canal  (the extreme version)

You get the point…… Continue reading