DOWNTOWNSAN MATEOASSOCIATION
P R E P A R E D B Y :
M A C K E N Z I E J A K O U B E K
E x e c u t iv e D ir e c t o r
H Q @ D S M A .o r g / D S M A .o r g
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A N N U A L R E P O R T
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ACCOMPLISHMENTS AT A GLANCE
80+ Downtownmerchants directlyparticipated in DSMAsponsored events More than 50 newbusinesses opened inDowntown San Mateo
Facebook content wasviewed 1.7 million times
Instagram reached55,000 accounts
DOWNTOWN SAN MATEOASSOCIATION SUMMARY
The Downtown San Mateo Association (DSMA) remains
steadfast in its mission to maintain and enhance the
attractiveness and vibrancy of Downtown San Mateo.
Since 1986, DSMA has managed the Downtown Business
Improvement District, providing vital support to local
merchants and fostering a thriving, connected community.
Downtown San Mateo continues to serve as a center for
business and leisure, attracting visitors from throughout the Bay Area with its history, diverse community, renowned
culinary scene, and optimal location on the San Francisco Peninsula.
This fiscal year, Downtown San Mateo continued to feel
active and energized, particularly on weekends and during community events. Under the leadership of the Board of
Directors and Executive Director Mackenzie Jakoubek,
DSMA strengthened collaboration, governance, and
strategic oversight while continuing to prioritize community engagement as a key activation strategy. Increased
participation in regional events, new family-friendly
programming, and expanded partnerships helped further
elevate Downtown’s visibility and sense of place.
DSMA also focused on organizational health and
sustainability in FY2025–26, completing a financial review with Pettinelli Financial Partners to support strong fiscal management and transparency. With new Board
leadership in place and a continued emphasis on
partnerships, marketing, and public space activation,
DSMA is well-positioned to build on its momentum.
Strategic investments in cleanliness, beautification, and business support will ensure Downtown remains a
welcoming destination for residents, visitors, and
businesses alike.
$100k used forDowntown clean-up &beautification efforts M A Y 2 0 2 6
53,000 visits toDSMA.org
53,000 visits toDSMA.org
35 submissions to ouronline contact formused for safety andcleanliness requestsand other needs Reached 10,000Facebook followers
Nestled in the heart of the San Francisco Peninsula, Downtown San Mateo has once again proven to be a vibrant intersection of history, innovation, and community. Over this past fiscal year, the district hasn’t just maintained its unique character—it has deepened its impact, thriving as a welcoming, dynamic destination for residents and visitors alike.
At the center of this growth is the Downtown San Mateo Association (DSMA). Since 1986, when we were first designated by the City Council to manage the Downtown Business Improvement District, our mission has remained steadfast: to foster an environment where local merchants succeed and the community connects.
We take immense pride in the work accomplished throughout FY 2025–26. By focusing on intentional programming, robust business support, and community-driven events, we have amplified the energy in our streets. The vitality we experienced this year was no accident, it was the result of a commitment to collaboration, strategic activation, and the shared belief that a strong downtown is the heart of a strong San Mateo.
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I N T R O D U C T I O N
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2 DSMA’s efforts to raise the levels of energy
and community engagement is now
attracting high-caliber partners and new
events eager to be part of that success.
While we celebrate these wins, we remain
clear-eyed about the challenges that define
the current economic climate. FY2025–26
was marked by a mix of pressures. Broader
economic uncertainty, specifically rising
costs for groceries and food supplies,
impacted our business community. We have
heard from some merchants that revenue
has fluctuated compared to the previous
year, as the rising cost of living influences
consumer spending habits and foot traffic
patterns. In addition, we continue to see
slower weekdays and busy weekends, a
reflection of the hybrid work model.
Despite these headwinds, the outlook for
Downtown San Mateo remains positive.
When new entrepreneurs choose to open
their doors here, they consistently cite our
commitment to cleanliness and safety, our
welcoming community spirit, and the
undeniable "vibe" that makes this district a
standout on the Peninsula and broader Bay
Area.
"There’s a lot of vibes here."
- Overheard in Downtown San Mateo
This quote captures the pulse and attraction
of Downtown San Mateo, and it’s a
sentiment we hear often, if not those exact
words. As a central hub on the San Francisco
Peninsula, our district remains a premier
destination for commerce, leisure, and
community connection.
Our district is evolving in exciting ways.
Notably, this fiscal year saw the arrival of
new, high-profile businesses like Molly Tea,
Reposado, Whisper, Johnny’s, Tai Er, and
others that have boosted overall foot traffic.
Perhaps most exciting is our growing
entertainment options: the opening of two
arcade venues (Nakoko and Clawesome)
and an indoor children’s play center (Kiddo
Adventure) have added family-friendly fun to
our already robust culinary scene. Overall,
we saw more than 50 new businesses open
in Downtown San Mateo over the past year.
Further anchoring this vibrancy is the
continued success of the B Street pedestrian
mall. It remains a beloved community
centerpiece, serving as a social "living room"
that proves how essential safe, walkable
public spaces are to a thriving downtown.
This vibrancy has not gone unnoticed;
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D O W N T O W N S A N
M A T E O O V E R V I E W
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3 Downtown San Mateo, as defined by our Business Improvement District charter, is made up of businesses located within Tilton Ave and 9th Ave and just past El Camino Real all the way to El Dorado. This footprint is approximately 7 square blocks, and includes approximately 600 businesses.
The Downtown San Mateo Association
(DSMA) continues to strengthen its role as a
champion for Downtown’s businesses and
community. The updated Business
Improvement District (BID) assessments,
approved by City Council in 2022, have
enabled DSMA to expand operations and
better support the district. These resources
remain essential to maintaining a clean, safe,
and vibrant Downtown while fostering strong
partnerships with the City of San Mateo and
local organizations.
FY2025–26 also marked a year of transition
and growth for DSMA’s Board of Directors.
This fall, the organization voted Mark Bartos
(Bartos Architects), Rafat Haddad (3 Bees
Coffee), Debbie Soon (Self Help for the
Elderly), and Damon Zhao (Cathay Bank) in
as new Board members. Colleen Rafferty
(Christensen & Rafferty Fine Jewelry) served
as Interim President for approximately three
months, providing continuity and leadership
ahead of Board elections in January 2026.
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D S M A O V E R V I E W
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4 Following the elections, DSMA welcomed a
new Executive Committee, with Rafat
Haddad serving as President, Lorry Morales
(La Pinata) as Vice President, and Cathy
Levitt (Tri Counties Bank) as Treasurer.
We have re-energized our Beautification and
Cleanliness Committee, now led by Chair
Robert Anderson. The committee's mission is
to monitor the aesthetics of Downtown San
Mateo and identify areas where the DSMA,
the City of San Mateo, and other
stakeholders can improve.
To support strong governance and fiscal
stewardship, DSMA completed a financial
review of fiscal years 2023-24 and 2024-25
with Pettinelli Financial Partners (PFP). This
review, included as an attachment to this
report, analyzed our financial position, cash
flow, and operating results. PFP found that
DSMA remains financially stable with strong
liquidity, declining liabilities, and positive
operating cash flow. The report reflects our
organization’s ongoing commitment to
transparency and sound financial
management.
In addition to organizational advancements,
DSMA expanded its programming and
community presence. Highlights included a
Santa visit, creating a new family-friendly
holiday tradition, and increasing participation
and support for the San Mateo Area
Chamber of Commerce’s September Arts &
Culture Fest. As part of this effort, DSMA
introduced its new mascot, Mateo the Fox.
Looking ahead, DSMA remains committed to
expanding marketing initiatives, activating
public spaces, and fostering a thriving
business environment through strong
leadership, partnerships, and community-
focused programming.
Collaboration remains a central strategy,
with DSMA working closely alongside
partners including San Mateo Parks &
Recreation, the City Manager’s Office, Self-
Help for the Elderly, San Mateo County
Office of Arts & Culture, Age-Friendly San
Mateo, the San Mateo Area Chamber of
Commerce, and many BID members to bring
increased activity, events, and resources to
Downtown.
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5 President, Rafat Haddad, 3 Bees Coffee
Vice President, Lorry Morales, La Pinata
Treasurer, Cathy Levitt, Tri Counties Bank
Robert Anderson, Downtown Resident and
retired San Mateo PD
Mark Bartos, Bartos Architecture
Steve Carey, LifeMoves
Colleen Rafferty, Christensen & Rafferty
Fine Jewelry
Debbie Soon, Self Help for the Elderly
Joe Sully, Downtown Property Owner
Jillian Thomas, Mills-Peninsula Medical
Center
Susan Uzunoglu, Susan’s European Beauty
Damon Zhao, Cathay Bank
Mackenzie Jakoubek, Executive Director,
DSMA
D S M A B O A R D
DSMA activities focus on Community Engagement, BID Member Engagement, and Civic Partnership.
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DSMA FOCUS AREAS
COMMUNITYENGAGEMENT
Community engagement focuses on events and marketing. The goal is to drive traffic Downtown and connect the community with our wonderful and diverse businesses. The primary audiences for community engagement are Downtown workers, San Mateo and Peninsula residents, and visitors to local hotels and events.
Community Events & Activations, Fiscal Year 2025-26
HEAD WEST Marketplace (Jul 20, Aug
17, Sep 21, Oct 19, Nov 30, Mar 21, Apr 18,
May 16, Jun 20): HEAD WEST
Marketplace, with the support of DSMA,
brought 30-50 makers, crafter, artists,
and other local vendors to B Street the
third Sunday of every month. Downtown
visitors were delighted with the variety of
shopping opportunities in Downtown
San Mateo.
Downtown Express (Aug 3): DSMA and
sponsor Florian Orthodontics brought
kid-sized fun to the Farmer’s Market with
the San Mateo Express. The first 200
kids got an extra treat of free ice cream
from Cold Stone Creamery or Chill Spot
Rendezvous.
Reyna y su Trio (Aug 16): Roving
Mariachi, Reyna y su Trio, delighted
North B businesses and customers with
their beautiful traditional Mexican music.
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September Nights on B (Sep 11 & 18): A
Downtown San Mateo favorite! DSMA
supported these lively City sponsored
concerts through funding, promotion,
and participation.
San Mateo Arts & Culture Fest (Sep
28): DSMA was proud to step up as a full
partner in this San Mateo signature event
along with the San Mateo Area Chamber
of Commerce and the San Mateo County
Office of Arts & Culture. The Fest offered
a variety of live music, cultural
entertainment, local arts, and even a live
mural painting competition. This year,
DSMA created a scavenger hunt for kids
and brought out a real-life Mateo the Fox
mascot.
Jazz on B Street with Swingatto (Oct
4): Back by popular demand, Swingatto
filled the B Street pedestrian mall with
their lively acoustic tunes
BOOs and Brews on B Street & Trick
or Treating (Oct 25): A close
collaboration between the City of San
Mateo’s Parks & Recreation Department
and DSMA, BOOs and Brews on B Street
welcomed hundreds of kids to the B
Street and Cinema Plaza to enjoy games,
a creepy-crawly petting zoo, crafts, a
selfie station, and other Halloween
activities. DSMA coordinated with 40
Downtown merchants who provided
candy to adorable trick-or-treaters.
Small Business Saturday & Jazz on B
Street with the Melodic Outreach
Endeavor (Nov 29): Aragon High School
students coordinated our entertainment,
bringing two jazz bands and one vocal
ensemble to delight Small Business
Saturday shoppers. DSMA was there to
share information about Shop Small to
Win Big! and talk all things small
business with the community.
Sounds of the Season with Business
Casual (Dec 6): Award-winning a
cappella group, Business Casual,
brought their signature style, fusing
holiday and contemporary favorites.
Community organizers held the Santa
Mateo scavenger hunt the same night,
leading to an unmatched evening of
holiday cheer in San Mateo.
Las Posadas (Dec 7): The merchants of
North B Street welcomed their loyal
customers and Holiday Train visitors to
their storefronts with warm cider, gift
bags, and other treats. Spanish-
language Christmas carolers sang
throughout the block. The event was
coordinated by the North B merchants
with DSMA support.
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7 Downtown San Mateo Boba Day
(April 26): Boba fans from around the
Bay Area enjoyed specials, giveaways,
and treats at Downtown San Mateo
boba shops and other retailers. Chef
Martin Yan, Wendy Hsu, and Mayor
Adam Loraine selected the “Judges’
Choice” winner after tasting boba from
around the district. DSMA and
supporting partners provided fun
activities on B Street for families and
took votes for “Downtown San Mateo’s
Favorite Boba 2026.”
Mother’s Day pop up (May 10): DSMA
provided a beautiful backdrop for family
photos on Mother’s Day.
Love Local (May 30): Celery Retail, with
support from DSMA, brought local
vendors and family-friendly activities to
B Street to help kick off the summer.
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Holiday Train “Celebration Station”
(Dec 7): While community members
waited to board Caltrain’s Holiday Train,
DSMA hosted entertainment from
Melodic Outreach Endeavor, the
Peninsula Dance Academy, Core
Taekwondo, and the Hillsdale High
School Chamber Singers, plus balloon
twisting from Joy in the Air Balloons.
Santa in Downtown San Mateo (Dec
21): Santa and his elf posed for photos
with San Mateo families at Lions Den
Shave Parlor and 3 Bees Coffee, thanks
to a partnership with Izzo Family Therapy.
Lunar New Year (Jan 24): Our third
annual Lunar New Year in Downtown
San Mateo provided an opportunity to
welcome the year of the horse with our
community and collaborate with many
local businesses and organizations.
Sponsors and supporters included
Florian Orthodontics, the City of San
Mateo, San Mateo Parks and Recreation
Department, and the San Mateo Area
Chamber of Commerce. Booth
participants included Self-Help for the
Elderly, the Asian American Curriculum
Project, Tri Counties Bank, CAM Edu, and
the San Mateo Public Library. Our Lion
Dance parade stops were Anton SV
Patisserie, East West Bank, Kiddo
Adventure, Taste of Sha Xian, Cathay
Bank, Superstar Dim Sum, Y Salon, My
Dumpling, Revolution Hair Studio,
SimplyCake, Fanloli, Nakoko, Dough
Zone, and Susan European Beauty.
San Mateo Sports Warm Up (Feb 7):
The CSM Bulldogs football team (back-
to-back state champs!), the Belmont
Brass Wrists arm wrestling league, and
our sponsor, Perform for Golf, helped the
community enjoy some friendly, sporting
competition on a beautiful Saturday in
Downtown San Mateo.
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8 Wow that’s cool! Didn’trealize we have So manygreat activities! D u e t o y o u r i n p u t t h e d o w n t o w n m a l l i s b u z z i n g a n d I b e l i e v e w i l l o n l y g e t t o b e m o r e o f a n a t t r a c t i o n i n S a n M a t e o .
- C h a r l i e C h i n
R e s i d e n t & M u s i c i a n
S a n M a t e o . p l e a s a n t
s u r r o u n d i n g s . g o o d f o o d
a n d d r i n k . w a l k a b l e . l i v e l y .
u n p r e t e n t i o u s .
So many wonderful events inDowntown San Mateo!
G o i n g d o w n t o w n t o d a y m a d e m e
p r o u d t o b e a S a n M a t e o
r e s i d e n t . B S t r e e t w a s p a c k e d , C e n t r a l P a r k w a s b u z z i n g , a n d i t w a s f u l l o f d i v e r s i t y o f a l l k i n d s .
COMMUNITY FEEDBACK
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Marketing & Brand Engagement
In FY2025–26, the DSMA executed a multi-channel marketing strategy designed to amplify the Downtown San Mateo brand. By blending digital storytelling with physical placements, we ensured that our district remained a top-of-mind destination for residents and regional visitors.
Digital Strategy & Social Growth
Our digital platforms serve as the "virtual front door" to the district. We reached a major milestone in February 2026, surpassing 10,000 Facebook followers. Our content strategy focused on information sharing and visual storytelling, utilizing professional photography and video to capture the "vibe" of our storefronts and public space while sharing important business updates.
Audience Expansion: We saw remarkable year-over-year growth, gaining 2,800 Instagram followers and 2,100 Facebook followers. Facebook page visits increased by 47%, while Instagram engagement rose by 19%.
Direct Communication: Our email outreach continues to be a vital tool for both the public and our merchants. Subscription rates for our community newsletter grew by 21%, while our business member newsletter saw an 8% increase.
Web Performance: Between March 2025 and February 2026, our website remained a critical resource. The most-visited pages included our Home Page, the Restaurant Guide, and the 2025 Boba Day landing page. Most visits resulted from Google searches, but we were also pleased to see referrals from the City of San Mateo’s website as well as other local digital resources like Klabbit and San Mateo Scoop.
Impactful Campaigns: We introduced a successful recurring feature, “What’s Happening Downtown this Weekend,” which provided consistent, actionable value to our followers.
Other recurring campaigns like “Reviewsday Tuesday” and “Sunday Blast from the Past” continue to appeal to our audiences.
Advertising & Outreach
Beyond the screen, we maintained a strong physical presence throughout the Peninsula. Our advertising efforts focused on meeting potential visitors where they live and play.
Outdoor Marketing: We placed high-visibility posters and print ads at high traffic locations, including San Mateo On Ice, the Autumn Moon Festival, and Eggstravaganza. We also utilized a marquee ad during the San Mateo County Fair to capture peak seasonal crowds.
The Restaurant Guide: Our premier physical asset, the Downtown San Mateo Restaurant Guide, was updated and distributed through local businesses, community events, and Peninsula hotels, reinforcing our status as a "foodie’s paradise." Targeted Media Partnerships: To draw in neighboring communities, we secured paid advertisements and community features in the Palo Alto Daily Post (notably for the HEAD WEST Marketplace) and San Mateo Scoop.
Event Promotion: Comprehensive flyer and poster campaigns were deployed throughout the district and surrounding cities to drive attendance for DSMA signature events.
Face-to-face: DSMA Leadership spoke with groups such as the Assistance League to share exciting updates to our Downtown. Word of mouth continues to be a significant way to get the word out about the vibrancy of Downtown San Mateo.
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Palo Alto Daily Post, Nov 2025
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San Mateo Scoop, Mar 2026
PIASC Pensogram, Mar 2026
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BID MEMBERENGAGEMENT
Small Business Saturday & "Shop Small to Win Big!"
We collaborated with the San Mateo Area Chamber of Commerce on the second annual “Shop Small to Win Big!” campaign. By incentivizing local spending between November 28 and December 12, we successfully drove shoppers to our independent retailers and more importantly, helped build long-lasting excitement around shopping small.
The Incentive: A coveted prize drawing featured donations from eight local favorites, including Golden Moon Gallery, Porterhouse, and Elements Massage.
Digital Storytelling: We partnered with filmmaker Gary Magill to produce short-form videos featuring Anatolian Market and Golden Moon Gallery (plus two businesses outside of Downtown), which brought the human stories behind our storefronts to life on YouTube and DSMA.org.
Community Presence: Small Business Saturday was further activated by our "Sounds of the Season" event, which featured live performances from student musicians from Aragon High School.
While membership in the Business Improvement District (BID) is automatic for those with a district address, the DSMA worked throughout the year to ensure that awareness and participation translated into real value. In FY 2025–26, we focused on delivering results for our diverse business community through high-visibility campaigns, networking opportunities, and direct support.
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Connecting Businesses to the Community
The DSMA focused on connecting merchants with the community through creative, event- based partnerships:
Santa Visit: Lions Den Shave Parlor and Izzo Therapy collaborated with us to host Santa Claus for photos, while 3 Bees Coffee served as the vital hub for children’s letters to the North Pole.
Lunar New Year: Our third annual Lunar New Year festivities saw 14 businesses participate as official parade stops. Lion Dancers performed at their storefronts and businesses engaged visitors through dedicated booth participation.
The Downtown Express: Sponsored by Florian Orthodontics, this kids' train event integrated Cold Stone Creamery and Chill Spot Rendezvous, driving families directly to their doors for complimentary treats.
San Mateo Sports Warm Up: Perform for Golf served as a sponsor, bringing a putting green to B Street and successfully converting event-goers into in-store visitors.
Trick or Treat Spots: 40 businesses participated in Boos and Brews on B Street, bringing potential customers right to their storefronts.
Business Support & Recognition
Our year-round support initiatives included:
One-on-one Support: DSMA leadership met with both prospective and current Downtown businesses to address specific needs and issues. The topics covered a wide range, including searching for available storefronts, proposing collaborations, troubleshooting inconsistent foot traffic, and assisting with outreach to social media content creators.
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New Business Outreach: New businesses
received a welcome packet and a direct
line to DSMA support, ensuring they were
invited to participate in meetings and
district events.
Celebrating Vibrancy: We recognized
holiday spirit with the “Best Holiday
Decorating 2025” awards, with top honors
going to Espetus, Lions Den Shave Parlor,
and Bay Watch.
Networking & Advocacy: In partnership
with the San Mateo Area Chamber of
Commerce, we co-hosted the "Mix &
Mingle" to foster essential business-to-
business connections.
Direct Communication: Our monthly
Member News email reached over 600
subscribers and maintained a consistent
50%+ open rate, serving as a critical
resource for business tools, resources, and
news.
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CIVICPARTNERSHIP
The DSMA served as a vital liaison between the district and the City of San Mateo. By working routinely with Public Works, Parks & Recreation, the San Mateo Police Department, and the City Manager’s Office, we helped to ensure that the needs of Downtown were heard. Additionally, we were able to disseminate important messages from the City of San Mateo to our members.
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Downtown Beautification, Cleanliness, and Safety
In FY 2025–2026, we took a proactive approach to maintaining the district’s "curb appeal" and ensuring a welcoming environment for all visitors:
Dedicated Maintenance: We funded daily porter services seven days a week to address litter and immediate cleanliness issues and as-needed “hot spot” power washing.
Targeted Sanitation: The DSMA Beautification & Cleanliness Committee conducted regular district "walk-arounds" to identify maintenance gaps. We coordinated extra power washings for identified "hot spots" to supplement standard City services.
Community Feedback: We maintained an online reporting tool on DSMA.org, allowing the community to submit real-time cleanliness and safety suggestions and concerns.
Safety Coordination: We held regular communications with the San Mateo Police Department to enhance the security and safety of the district.
Visual Enhancements: To boost holiday vibrancy, we expanded our festive banner program beyond B Street to include 3rd and 4th Avenues and hosted the "Best Holiday Decorating" awards.
Future Aesthetics: We initiated high-level discussions with stakeholders regarding the creation of art murals on private property to further activate our streetscape.
Advocacy
Beyond maintenance, the DSMA acted as a strategic partner in regional and city initiatives:
Regional Event Planning: We met regularly with stakeholders to prepare for the excitement of large-scale Bay Area sporting events in 2026.
Resource Facilitation: We led business outreach for City programs, including Age-Friendly San Mateo, small business grant opportunities, flood prevention, and emergency preparedness.
Promotional Support: We served as a marketing megaphone for City-sponsored events such as the Central Park Music Series, Winter Wonderland, Eggstravaganza, and September Nights on B.
Problem Solving: We acted as a first point of contact for business concerns, resolving issues directly or facilitating connections with the appropriate civic departments to find solutions.
Stakeholder Buy-in: We hosted monthly discussions during DSMA Board meetings.
Discussions included representatives such as SamTrans, Public Works, and the Police Department to ensure our members had a seat at the table for decisions that impact them directly.
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Successful:
Completed a third-party financial review to ensure transparency and fiscal responsibility.
Provided supplemental power washing and daily porter services to maintain a standard of cleanliness beyond baseline city services.
Executed a robust calendar of pop-ups and signature events on the B Street Pedestrian Mall, driving energy and visibility to the district.
Maintained deep partnerships with City staff and conducted regular "walk-arounds" with the Board and stakeholders to identify and resolve maintenance issues.
Refreshed and distributed the Downtown San Mateo Restaurant Guide and the Your Role in a Clean Downtown brochure.
Provided financial and promotional support for regional highlights, including Music in the Park, San Mateo County Pride, and September Nights on B Street.
Maintained a consistent print advertising schedule in the San Mateo Daily Journal.
Continuing Efforts:
We are actively recruiting new Board members and refining participation guidelines to ensure diverse and engaged leadership.
Work continues on campaigns to broaden the Downtown brand’s reach beyond the immediate San Mateo area.
We are focused on strengthening collaborations with local organizations and building relationships with developers and tech companies entering the district.
Efforts to expand digital advertising and introduce new features to DSMA.org are ongoing, with success measured via Google Analytics.
Maintaining regular representation at City Council, Commission meetings, and other meetings to advocate for Downtown San Mateo remains a priority.
Delayed:
The exploration of a college internship or other part time help for DSMA operations has been deferred to a future cycle.
Downtown Specific Plan support will begin when the City kicks off this initiative.
PERFORMANCE AGAINST GOALS: FY 2025–26
GOALS
The nature of the DSMA’s work is one of continuous improvement; even tasks marked "Successful" need ongoing attention and maintenance. Below is a status report on the strategic priorities established for the 2025–2026 fiscal year.
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PLANS FOR FY 2026-27 AT A GLANCE
Increase budget forcleanliness andbeautification by 25% Encourage Downtownbusiness participationin cleanliness and othercommunity initiatives Update by-laws andenhance boardparticipation throughclear communicationand defined goals Increase marketing &activation budget,magnifying theDowntown San Mateobrand Under the leadership of our new Board President, Rafat Haddad, the DSMA mission for the coming year is crystal clear: To ensure Downtown San Mateo is clean, safe, and vibrant. To achieve this vision, we have established the following priorities for FY 2026–27:
Governance & Leadership Excellence
Implement clear communication regarding the specific roles and responsibilities of Board members as ambassadors for the DSMA.
Enhance Board meeting structures to further streamline information-sharing and accelerate decision-making while encouraging participation.
Update the DSMA bylaws to reflect the current best practices and the evolving needs of a 2026 business environment.
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LOOKING AHEAD: GOALS FOR FY 2026–27
Community & Committee Reinvigoration
Reenergize the Cleanliness and Beautification
Committee and build specialized task forces to
tackle specific district goals.
Increase direct touchpoints between the Board
and BID members to ensure our initiatives
remain aligned with merchant needs.
Encourage storefront owners to take an active
role in Downtown’s appeal through a “lead by
example” sidewalk maintenance initiative and
sharing professional cleaning resources.
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P R O P O S E D D O W N T O W N E V E N T C A L E N D A R F I S C A L Y E A R 2 0 2 6 - 2 7
E v e n t s s u p p o r t e d b y , n o t c o - s p o n s o r e d o r h o s t e d b y D S M A a r e i n i t a l i c s July 11 & 12: Bay Area Fit Fest
July 18: HEAD WEST Marketplace
July 19: Bay Area Moms Back to School
Bash
August 1 & 2: Clawesome Family Fest
August 15: HEAD WEST Marketplace
September 10 & 17: September Nights on
B
September 19: HEAD WEST Marketplace
September 26: San Mateo Arts & Culture
Fest (with San Mateo Area Chamber &
SMC Office of Arts & Culture)
October 17: HEAD WEST Marketplace
October 24: BOOs on B Street (with
Parks & Rec)
November 21: HEAD WEST Marketplace
November 28: Small Business Saturday
pop up
(Tent) December 5: Las Posadas (North
B Merchants event with DSMA support)
December 5: Winter Wonderland (DSMA
supporting)
M A Y 2 0 2 6
1 7
December 5: Santa Mateo (DSMA
supporting)
December 19: HEAD WEST Marketplace
January 23 (tentative date): Lunar New
Year
January: Peninsula Restaurant Week (SF
Peninsula campaign)
February 14: Valentine’s Day pop up
February (date TBD): Pop up event
March (date TBD): Pop up event
March (date TBD): HEAD WEST
Marketplace
April (date TBD): HEAD WEST
Marketplace
Late April (date TBD): Downtown San
Mateo Boba Day
May 10: Mother’s Day pop up
May (date TBD): HEAD WEST
Marketplace
June (date TBD): HEAD WEST
Marketplace
June (date TBD): Pop up event
Additional pop up events may be added as budget and schedules allow.
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BUDGET
Fiscal Year 2025–26 marked DSMA’s third year operating under the updated assessment structure approved by the City Council. Revenue in FY2023–24 ($443k) came in higher than budgeted, due in part to an $11,000 grant and adjustments related to assessment billing.
Revenue in FY2024–25 declined as those assessments were reconciled. The final revenue collected in FY2025–26 is expected to more closely reflect the intended assessment levels.
Event sponsorships were another source of revenue this year. Since gifts to DSMA are not tax- deductible, we keep sponsorship fees low and use them more as a marketing tool and way to engage our BID members. They help to subsidize events, but do not cover costs entirely.
Less than one percent of DSMA income came from interest on one savings account and one CD.
Interest had not previously been included in the revenue reporting. We expect interest income to remain relatively insignificant in the next fiscal year.
The expense highlights are:
Marketing and Activation
Community events: Budget is increasing from $35k to $40k to improve on recurring events and give some room for additional pop up events.
Advertising and Promotion: Increasing this budget to $60k to build digital and print advertising
Banners: The large expense in FY2025-26 was due to printing new holiday banners for 3rd and 4th Aves. Going forward, we will only have to pay for banner storage and installation each year.
Civic Partnership
Downtown Cleaning & Beautification: The porter and power washing budget will increase slightly for next year, and we are adding a line item for beautification projects to improve the appeal of our Downtown.
Payroll & Professional Services: The budget includes a small increase, allowing for a cost of living raise for the Executive Director.
A contingency fund for unplanned expenses
We maintain a cash reserve of approximately $350,000 (as of March 27, 2026) held in a money market account and a CD. DSMA has historically used reserves to support Downtown businesses during periods when assessment levels were intentionally reduced, such as during COVID-19. Given the current economic uncertainty with rising costs, maintaining a healthy reserve provides flexibility to respond to future challenges and continue supporting the business community as needed.
ESTIMATED INCOME ANDEXPENSES FOR FY 2026-27
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1 8
F Y 2 0 2 5 - 2 6 A N N U A L R E P O R T
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1 9
DSMA is incredibly grateful for the use of office space granted by the City of San Mateo. We redirect that savings towards programs that support our mission. While DSMA doesn’t utilize any city equipment, the shared space fosters a closer relationship between DSMA, the City, and Downtown businesses. We would like to express our sincere gratitude to the City for providing the shared space and for its ongoing support and partnership.