Microsoft Sidewalk & MRG:
Early Trials in Scaling Hyperlocal Advertising
Microsoft Sidewalk & MRG:
Early Trials in Scaling Hyperlocal Advertising
Microsoft Sidewalk hit sales goals but revealed the high costs and challenges of scaling hyperlocal content—lessons that shaped future strategies.
Exceeded Sidewalk’s sales revenue targets.
Activated distribution and coupon-book partnerships.
Tested one of the first hyperlocal editorial + advertising models
The Timeline
To date, we have sold over 50,000 merchant accounts and worked with some of the most credible brands.
1995–1996
Origin & Development
Spawned from Peter's days at Microsoft, Merchant Resource Group (MRG) was founded on the simple principle that small businesses should be able to leverage tech without having to learn it.
1995–1996
Origin & Development
Spawned from Peter's days at Microsoft, Merchant Resource Group (MRG) was founded on the simple principle that small businesses should be able to leverage tech without having to learn it.
1996–1997
Launches & Partnerships
Sidewalk launched in Seattle, New York, and Boston, with editorial and distribution partnerships powering listings and local coverage.
1996–1997
Launches & Partnerships
Sidewalk launched in Seattle, New York, and Boston, with editorial and distribution partnerships powering listings and local coverage.
1997–1998
Business Model & Sales Push
Microsoft rebranded as MSN Sidewalk, expanding beyond entertainment into directories, couponing, and buyer’s guides. Partnerships with companies like Entertainment Publications supported sales and marketing.
1997–1998
Business Model & Sales Push
Microsoft rebranded as MSN Sidewalk, expanding beyond entertainment into directories, couponing, and buyer’s guides. Partnerships with companies like Entertainment Publications supported sales and marketing.
1999
Acquisition by CitySearch
Microsoft sold the arts & entertainment portion of Sidewalk to Ticketmaster Online–CitySearch, taking a 10% equity stake and handing over city guide coverage. CitySearch’s reach jumped from 33 to 77 cities.
1999
Acquisition by CitySearch
Microsoft sold the arts & entertainment portion of Sidewalk to Ticketmaster Online–CitySearch, taking a 10% equity stake and handing over city guide coverage. CitySearch’s reach jumped from 33 to 77 cities.
What we learned
Acting in a national sales capacity for Sidewalk, we exceeded our sales revenue targets but MRG helped with what was an early attempt at hyperlocal editorial + listings + advertising, a tough business: building a national network of local editorial guides is expensive and ad revenue (and local sales infrastructure) didn’t scale easily in the 1990s.
Our analysts at the time and later retrospectives say Microsoft struggled with the economics and execution of local content and decided to focus MSN on directories and other services while handing arts/entertainment to a specialist like CitySearch.
We learned a lot of lessons early and humbled ourselves. Effecting execution isn’t easy but MRG would persist and we would get better.
What we learned
Acting in a national sales capacity for Sidewalk, we exceeded our sales revenue targets but MRG helped with what was an early attempt at hyperlocal editorial + listings + advertising, a tough business: building a national network of local editorial guides is expensive and ad revenue (and local sales infrastructure) didn’t scale easily in the 1990s.
Our analysts at the time and later retrospectives say Microsoft struggled with the economics and execution of local content and decided to focus MSN on directories and other services while handing arts/entertainment to a specialist like CitySearch.
We learned a lot of lessons early and humbled ourselves. Effecting execution isn’t easy but MRG would persist and we would get better.
The Timeline
To date, we have sold over 50,000 merchant accounts and worked with some of the most credible brands.
1995–1996
Origin & Development
Spawned from Peter's days at Microsoft, Merchant Resource Group (MRG) was founded on the simple principle that small businesses should be able to leverage tech without having to learn it.
1996–1997
Launches & Partnerships
Sidewalk launched in Seattle, New York, and Boston, with editorial and distribution partnerships powering listings and local coverage.
1997–1998
Business Model & Sales Push
Microsoft rebranded as MSN Sidewalk, expanding beyond entertainment into directories, couponing, and buyer’s guides. Partnerships with companies like Entertainment Publications supported sales and marketing.
1999
Acquisition by CitySearch
Microsoft sold the arts & entertainment portion of Sidewalk to Ticketmaster Online–CitySearch, taking a 10% equity stake and handing over city guide coverage. CitySearch’s reach jumped from 33 to 77 cities.
What we learned
Acting in a national sales capacity for Sidewalk, we exceeded our sales revenue targets but MRG helped with what was an early attempt at hyperlocal editorial + listings + advertising, a tough business: building a national network of local editorial guides is expensive and ad revenue (and local sales infrastructure) didn’t scale easily in the 1990s.
Our analysts at the time and later retrospectives say Microsoft struggled with the economics and execution of local content and decided to focus MSN on directories and other services while handing arts/entertainment to a specialist like CitySearch.
We learned a lot of lessons early and humbled ourselves. Effecting execution isn’t easy but MRG would persist and we would get better.
CASE-STUDIES
See our partnership success stories
Every partnership tells a story. From Microsoft to Deluxe, Endurance, and beyond, Merchant Resource Group has helped leading companies unlock new revenue, scale faster, and capture greater enterprise value. Explore how our strategies, playbooks, and precision execution have turned complex challenges into measurable results across payments, and ecommerce.
CASE-STUDIES
See our partnership success stories
Every partnership tells a story. From Microsoft to Deluxe, Endurance, and beyond, Merchant Resource Group has helped leading companies unlock new revenue, scale faster, and capture greater enterprise value. Explore how our strategies, playbooks, and precision execution have turned complex challenges into measurable results across payments, and ecommerce.
CASE-STUDIES
See our partnership success stories
Every partnership tells a story. From Microsoft to Deluxe, Endurance, and beyond, Merchant Resource Group has helped leading companies unlock new revenue, scale faster, and capture greater enterprise value. Explore how our strategies, playbooks, and precision execution have turned complex challenges into measurable results across payments, and ecommerce.