1.
Vermont Private Investment Landscape 2021
Cairn G. Cross, Co-founder FreshTracks Capital
www.linkedin.com/in/cairncross
@vtcairncross
3/31/2022
Number of Investments Increased, While Investment Dollars Soared Year-Over-Year

2.
FreshTracks Has Been Active in the Local Ecosystem for
more than 2 Decades
• Formed in 2000
• Investing from our 5th
fund
• Completed
investments in ~50
Vermont companies

3.
Agenda
• 2021 U.S. Venture Capital Markets
o Source: Q4 2021 Pitchbook/NVCA Venture Capital Monitor
• 2021 Vermont Venture Capital Data
o SEC Form D Filings and Reg CF Filings, proprietary data
• Notable Trends in the VT Ecosystem
• Post COVID Vermont thoughts

4.
2021 U.S Venture Capital Trends:
Total Value Up, Deal Count Up

5.
2021 U.S. VC Investments:
Almost Half are $1MM - $10MM
19%
34%
47%

6.
Agenda
• 2021 U.S. Venture Capital Markets
o Source: Q4 2021 Pitchbook/NVCA Venture Capital Monitor
• 2021 Vermont Venture Capital Data
o Source: SEC Reg D and Reg CF filings plus proprietary data
• Notable Trends in the VT Ecosystem
• Post COVID Vermont thoughts

7.
VT VC Deals Completed more than doubled over past
decade, Investment Dollars Soared in 2021
• Steady upward trend in number of investment transactions
• Massive 2021 dollar increase due to 9-figure investment rounds at Beta Air and Polly
• FreshTracks participated in approximately 32% of the 2021 investment transactions
$0
$100,000,000
$200,000,000
$300,000,000
$400,000,000
$500,000,000
$600,000,000
$700,000,000
2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021
Private Investment Dollars
0
5
10
15
20
25
30
35
40
2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021
No. of VT VC Deals Completed

8.
VT Average Deal Size Soared due to Beta and Polly
• Each bar shown is a 3 year
rolling average to smooth
data.
• Despite the “smoothing”
the effect of Beta and Polly
is clear.
$0
$1,000,000
$2,000,000
$3,000,000
$4,000,000
$5,000,000
$6,000,000
$7,000,000
$8,000,000
$9,000,000
2012 2013 2014 2015 2016 2017 2018 2019 2020 2021
Average Investment Size Per Company

9.
Removing 5 Largest VT transactions (>$10MM),
Average Size of Rounds is Still Growing
Smaller Seed rounds ($0 to
$1MM) increased on average
by more than $150K
$0
$100,000
$200,000
$300,000
$400,000
$500,000
2020 2021
$243,000 $418,000
Average Size of Rounds < $1MM
Early Stage rounds ($1MM+
to $10MM) increased on
average more by than $800K
$0
$1,000,000
$2,000,000
$3,000,000
$4,000,000
2020 2021
$2,454,000 $3,292,000
Average Size of Rounds $1MM to
$10MM

10.
91% of Total Dollars Allocated Went to 3 VT
Companies
• 91% of dollars went to 3 larger
companies via 5 separate
growth financing transactions
(Beta, Polly, SuperPlastic)
• 8% of dollars went to early/mid
stage investments in growing
companies (financings of
$1MM+ to $10MM)
• 1% of dollars went seed stage
investments in startups & small
companies (financings up to
$1MM)

11.
Half of the Vermont Private Investment Transactions
were less than $1MM
39.5%
The larger transactions are generally
preferred stock (except two bridge
loans which converted into equity
prior to year-end)
19 transactions Were $1MM or Less
• 10 Preferred Stock
• 6 convertible debt
• 2 SAFE
• 1 Common Stock
50%
10.5%

12.
Consumer / Food / Bev Was the
Most Active Category in VT
• 35 transactions used Reg D (sale of equity
or debt without the need to register with
the SEC)
• 3 transactions used Reg CF (Crowdfunding).
All were Consumer companies: Piecemeal
Pies, Shacksbury Cider & Tost
Consumer / Food / Beverage / Adult Bev 8
Aerospace 7
MarTech 4
InsurTech 3
EdTech 3
Media 2
Medical Technology / Health 2
Energy Tech 2
AgTech 1
Other 6
Total 38

13.
Number of Investors in Each Round and Average
Investment Size per Investor Generally Increasing
Round Size Average Investors
Required
Average Check Size
Per Investor
$0 to $1MM 5 $80K**
$1MM - $10MM 11* $310K
$10MM and up 41 $3.5MM
* Same as 2020
** less than 2020

14.
Percentage Increase in Vermont VC Investment
Outpaced the rest of the U.S. During the Pandemic
• Largely due to
Polly & Beta
• But still impressive
to see the increase
in Vermont VC
funding by dollars
since the start of
the pandemic

15.
Agenda
• 2021 U.S. Venture Capital Markets
o Source: Q4 2021 Pitchbook/NVCA Venture Capital Monitor
• 2021 Vermont Venture Capital Data
o SEC Reg D and Reg CF filings, proprietary data
• Notable Trends in the VT Ecosystem
• Post COVID Vermont thoughts

16.
Investments of Note (Reg D offerings) –
Polly & Beta Technologies
F/K/A DealerPolicy (Insurance Technology) Beta Air (EVTOL aircraft)

17.
Notable Exits
Acquired by
Acquired by
Acquired by

18.
Traction in Vermont Industries of Note
Marketing Technology (MarTech) Aerospace

19.
Active VT-Based Investment Firms & Syndicates
•J.H. Capital (family office)
•VT Seed Capital Fund (VCET)
•VSJF Flexible Capital Fund
•FreshTracks Capital
•North Country Angels

20.
Shameless
Promotion –
Thanks to CB
Insights
FreshTracks
remains the most
active VC in VT

21.
Agenda
• 2020 U.S. Venture Capital Markets
o Source: Q4 2020 Pitchbook/NVCA Venture Capital Monitor
• 2020 Vermont Venture Capital Data
o Source: 2010 – 2019 data from NVCA Pitchbook
o Source: H1 2020 NVCA Pitchbook Data, plus Reg D and Reg CF filings
• Notable Trends in the VT Ecosystem
• Post COVID Vermont thoughts

22.
Final Thoughts: Vermont VC
Ecosystem Continues to Strengthen
• Solid increase in number of financings during past
decade. Trend expected to continue. 50+
transactions annually by 2025?.
• Annual $ invested
sometimes
skewed by large
deals. 2021 fits
this profile.
• Syndicates broadening and deepening.
Provides healthy competition for deals
and increases access to capital.
Multiple entry points for
entrepreneurs.

23.
Final Thoughts: Supply of VT Venture Capital
Continues to Come Online
• Expect that by mid-2023 there should be
$50MM+ early stage “dry powder” capital
held by active Vermont Based investment
groups waiting to be deployed.
• Continued inflow of Non-Vermont capital for many
financings (example: Polly and Beta).
S/B excellent time to raise
money for entrepreneurs
Footnote: Subsequent to
compiling this report we learned
of another Vermont based
company which raised $6.2MM
during 2021 and which has
has not been reflected