Sackcloth & Ashes

Founder of Sackcloth & Ashes, Bob Dalton was inspired to help the homeless population when his mother, a hardworking single mother, found herself living on the streets in 2013. Because of his mother's story, Dalton was inspired to call his local homeless shelters to ask what they needed most – they all said blankets. That's when he founded Sackcloth & Ashes. For every blanket purchased, Sackcloth & Ashes gives a blanket to your local homeless shelter.

Finance, Legal, Strategy
Start Date
End Date
Based In
Oregon & California
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I met Bob Dalton, founder and CEO of Sackcloth & Ashes, in early 2018 through an introduction from a mutual friend. Bob was seeking advice on the financial side of his business, including fundraising. While I was initially impressed with Bob's unique understanding of the influencer space and his grasp of millennial customers, I discovered his pure grit is what has made him successful. Bob started Sackcloth & Ashes after seeing his mom fall on hard times and get shuffled through homeless shelters. I am inspired by Bob's mission-driven approach along with the ability to encourage C-level women and men to give back. I am proud to continue to work with the company in the CFO capacity.

My work with Sackcloth has evolved from the initial fundraising needs into a longer-term partnership with the company. I spend about 10 - 20 hours/week working with Sackcloth. My role is currently comprised of three primary areas: Finance, Legal, & Strategy.


The finance needs began by servicing the request of prospective investors, such as building a financial model, cash flow forecasting, and financing structures. I also saw a need for the company to improve the structure of its accounting records and relationships. I migrated the company to Pilot in October 2018 and continue to manage the relationship by providing monthly figures needed to complete the month-end close process. Additional finance responsibilities have come to include the annual tax process, maintenance of financial models, and constructing a financial narrative for ongoing conversations with prospective investors and funding sources.


While I don't any formal legal training, I've come to appreciate contract law through my work with Sackcloth. What seems like an overly-complex document, actually contains 5 - 10 key terms, structured as building blocks (i.e., paragraphs). At Sackcloth, I develop and leverage relationships with external legal firms for initial template agreement creation. Using templates, I've structured agreements for Sackcloth's B2B contracts, consulting agreements, financing offerings, and copyright matters.

My experience with contract law has not only allowed me a greater understanding of external agreements (i.e., a new lease), but also shifted my mindset for risk-management. Legal agreements can be used to codify a mutual understanding, while providing protection in various scenarios. I will continue to learn about the legal profession, but my initial understanding has been immensely valuable in other areas of work.


The strategy component began through advising on individual business decisions, but evolved into a position of at least weekly consultations with the purpose of supporting the founder and to maximize the long-term value of the company. A quarterly board meeting and monthly executive meeting embodies my routine contributions. I am actively involved in customer negotiations, inventory management, incentive structures for independent consultants, and data analysis (rich dataset with over 30,000 sales records).

I find my work with Sackcloth incredibly fulfilling. All my work with Sackcloth (and startups in general) can be summarized as supporting the vision of the founder.