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Self-Made Boss: Advice, Hacks, and Lessons from Small Business Owners by Jackie Reses & Lauren Weinberg

April 3, 2022 Melanie Hawken

Book Review

When it comes to getting practical advice, small business owners too often don’t know where to look, but Longtime Square executives Jackie Reses and Lauren Weinberg, authors of the book Self-Made Boss: Advice, Hacks, and Lessons from Small Business Owners, want to change all that. Part starter-kit, part encyclopedia, and part inspiration, Self-Made Boss is an essential survival guide for small businesses. Sure, you can find all sorts of high-level strategic tips from Fortune 500 CEOs. But what if you own a restaurant, and you’re trying to figure out how to source good fish, or if you’re looking to increase revenue from your plumbing supply store? You’ll be running a lot of Google searches before you hear from someone who’s actually stood in your shoes.  


Longtime Square executives Jackie Reses and Lauren Weinberg, authors of the book Self-Made Boss: Advice, Hacks, and Lessons from Small Business Owners, reached out across the country, talking to dozens of entrepreneurs with valuable businesses―and invaluable advice. This book is the product of that research. Part starter-kit, part encyclopedia, part inspiration, Self-Made Boss is filled with information not just about who these small business owners are, but how they built their companies, step by step.  

How did they get their start? When did they decide to hire more staff? How did they set a course for growth? And when problems arose, how did they fight through them? You’ll hear from a second-generation ice cream shop owner on how to manage price increases; an oyster farmer finding new ways to stay afloat in the middle of a global pandemic; a roofer who refused to be denied or defined by her race and gender―and dozens of other small business owners making a big difference in their communities.  

No matter the size of your business today―or where you’re thinking about taking the jump tomorrow―you’ll find answers you can apply right away. 

Because there’s a common purpose that all small business owners share: the drive to build something from the ground up; the relentless pursuit of turning obstacles into opportunities and roadblocks into stepping stones. It’s tough and messy, hard-fought and hard-won. And above all, it’s something you can’t have when you work anywhere else―or for anyone else.  That’s what it means to be a Self-Made Boss. 

Author Quotes

Many entrepreneurs start their companies for the same reason…they see a problem in the world and decide to become part of the solution.

Throughout this book, you’ll hear from entrepreneurs who took a leap of faith to start a company…in every instance, they had an idea they were excited about and a plan to bring it to life.

No matter what kind of business they’re in, or why they started it, all small business owners have a common struggle. They’re all working to figure out how to best take an idea and turn it into reality - and make a living while they’re at it.

About the authors

Jackie Reses is the Chief Executive Officer of Luna Financial Group, a fintech building banking-related financial infrastructure for tech and crypto companies and the Chair of the Economic Advisory Council of the Federal Reserve Bank of San Francisco. Previously, she was the Executive Chairman of Square Financial Services, Capital Lead and Head of the People Team at Square Inc. (Block Inc). She has been named one of Forbes "Self Made Women," Fast Company’s “Most Creative People in Business,” and American Banker's “Most Powerful Woman in Finance."  Prior, she had leadership positions at Yahoo! and was a Partner at Apax Partners Worldwide, one of the largest private equity firms in the world. Jackie is also on the board of directors of Endeavor, Affirm and Nubank.  

Lauren Weinberg is the Chief Marketing Officer of Square, where she leads global Marketing and Communications for the $100B company that provides business solutions for millions of small business owners all over the world. She has been named on Forbes “CMO Next,” Brand Innovators “Top Women in Marketing,” and Fintech Hub’s “30 Most Influential Fintech Marketers.” Prior, she held leadership roles at Yahoo, MTV, and AOL. She is an AdWeek Executive Mentor and advises early stage startups.


Why LoA loves it…

We know that small businesses are the backbone of the economy, but we also know it’s a hard journey for many women entrepreneurs who are launching their businesses to get the right support and guidance in those early days. Usually, some of the best advice comes from those who have been there and done it before, felt the start-up pain, and have the experience to know how to learn the right lessons for next time. So Jackie and Lauren in their new book, Self-Made Boss, have brought together some of those personal experiences of small business owners who have built their companies from the ground up. This is a great book that feels like having a team of experienced business building cheerleaders on your side. — Melanie Hawke, founder & ceo, Lionesses Africa

In Essential Tags Books
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Tech FoundHER AFRICA CHALLENGE

MEET THE 10 FINALISTS — We look forward to announcing the winning women founders on 19 November 2025.


CELEBRATING 10 YEARS


LATEST PODCASTS

Lioness Radio Show Interview: Listen to Mr Jules Ngankam, Group Chief Executive Officer of the African Guarantee Fund, discussing the journey from Bias to Bankable - AGF’s Case for Financing Women Entrepreneurs.

Lioness Radio Show: Five Mozambican women entrepreneurs share their experiences of building successful green businesses and creating green jobs for local people. From an environmentally-friendly, high-impact skincare brand, to an innovative green transportation business transforming marine waste into bicycles, these Lionesses are making waves in Mozambique. Listen to their stories, learn from their experiences, and be inspired by their tenacity.


LIONESS WEEKENDER COVER STORIES

LIONESS WEEKENDER COVER STORY
Vanessa Mhlom, a South African wellness brand builder
Vanessa Mhlom, a South African wellness brand builder
Morongwe and Michelle Mokone, two social impact entrepreneurs building a high-growth, premium sustainable homeware business
Morongwe and Michelle Mokone, two social impact entrepreneurs building a high-growth, premium sustainable homeware business
Dr. Phindi Cebekhulu-Msomi, an agripreneur focused on climate-smart solutions
Dr. Phindi Cebekhulu-Msomi, an agripreneur focused on climate-smart solutions
Retang Phaahla, a pioneer for South Africa’s indigenous teas
Retang Phaahla, a pioneer for South Africa’s indigenous teas
Dr Margaret Kemigisha, a publishing entrepreneur passionate about childrens’ literacy
Dr Margaret Kemigisha, a publishing entrepreneur passionate about childrens’ literacy

IMAGE OF THE DAY. CELEBRATING WOMAN MADE IN AFRICA.

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Traditional craft elevated…We love the impact-driven accessories created by Márcia Nangy O’Connell, founder and artistic director of Dathonga Designs in Mozambique. Since 2010, she has establis
Image of the Day / Dounia Home

Statement lighting… from Dounia Home, the home of innovative, handcrafted and ethically made Moroccan lighting and home decor founded by Dounia Tamri-Loeper. Her company designs, produces and brings to market hi
Image of the Day / Mash. T Design Studio

Award-winning furniture design…We are big fans of talented South African designer Thabisa Mjo, founder of Mash. T Design Studio in Johannesburg, and these fabulous side tables are firm customer favouri
Image of the Day / Quazi Design

Sustainable Home Decor…If you want to make a statement with your interior design and home decor, and at the same make a contribution to supporting eco-friendly enterprise, then these unique decor pieces from Qu
Image of the Day / Eki

Silk Sensation…Nothing is quite as luxurious as silk, that’s why we love the ‘Africa on Silk’ collections from Eki, founded by Hazel Eki Osunde. Eki is known for its signature soft silks and ethereal c
Image of the Day / ‘57 Chocolate

Bean to bar luxury chocolate… Taste the difference with the finest chocolate lovingly produced by ‘57 Chocolate, the pioneer bean to bar chocolate manufacturer in Ghana, created by sisters Kimberle
Image of the Day / Kebe Home

Handcrafted home decor …We are big fans of the work of Manuela Kamadjou, an interior architecture and design entrepreneur who transforms homes and spaces in Cameroon through her business, Kebe Home. Her new Echo V
Image of the Day / Pichulik

Beautiful bracelets… Introducing The Aruba Bracelets by Katherine-Mary Pichulik, the founder and designer behind the Pichulik line of accessories. Pichulik is an ethical jewellery, accessories and womenswear atelie
Image of the Day / Eva Sonaike

Vibrant textile design…This striking textile design by Eva Sonaike caught our eye this morning. Like the rest of the world, we love the African aesthetic which is increasingly finding its way into global interio
Image of the Day / Adèle Dejak

Luxury statement accessories…We are big fans of luxury jewellery and accessories made with love and passion on the African continent, and Adèle Dejak in Kenya is the epitome of handmade luxury. The
Image of the Day / Dathonga Designs

Traditional craft elevated…We love the impact-driven accessories created by Márcia Nangy O’Connell, founder and artistic director of Dathonga Designs in Mozambique. Since 2010, she has establis Image of the Day / Dounia Home

Statement lighting… from Dounia Home, the home of innovative, handcrafted and ethically made Moroccan lighting and home decor founded by Dounia Tamri-Loeper. Her company designs, produces and brings to market hi Image of the Day / Mash. T Design Studio

Award-winning furniture design…We are big fans of talented South African designer Thabisa Mjo, founder of Mash. T Design Studio in Johannesburg, and these fabulous side tables are firm customer favouri Image of the Day / Quazi Design

Sustainable Home Decor…If you want to make a statement with your interior design and home decor, and at the same make a contribution to supporting eco-friendly enterprise, then these unique decor pieces from Qu Image of the Day / Eki

Silk Sensation…Nothing is quite as luxurious as silk, that’s why we love the ‘Africa on Silk’ collections from Eki, founded by Hazel Eki Osunde. Eki is known for its signature soft silks and ethereal c Image of the Day / ‘57 Chocolate

Bean to bar luxury chocolate… Taste the difference with the finest chocolate lovingly produced by ‘57 Chocolate, the pioneer bean to bar chocolate manufacturer in Ghana, created by sisters Kimberle Image of the Day / Kebe Home

Handcrafted home decor …We are big fans of the work of Manuela Kamadjou, an interior architecture and design entrepreneur who transforms homes and spaces in Cameroon through her business, Kebe Home. Her new Echo V Image of the Day / Pichulik

Beautiful bracelets… Introducing The Aruba Bracelets by Katherine-Mary Pichulik, the founder and designer behind the Pichulik line of accessories. Pichulik is an ethical jewellery, accessories and womenswear atelie Image of the Day / Eva Sonaike

Vibrant textile design…This striking textile design by Eva Sonaike caught our eye this morning. Like the rest of the world, we love the African aesthetic which is increasingly finding its way into global interio Image of the Day / Adèle Dejak

Luxury statement accessories…We are big fans of luxury jewellery and accessories made with love and passion on the African continent, and Adèle Dejak in Kenya is the epitome of handmade luxury. The

STARTUP STORIES. MEET THE WOMEN WHO’VE LAUNCHED.

Featured
Isabel Mandofa, a Mozambican woman entrepreneur building a successful, high-impact agri-food business
Isabel Mandofa, a Mozambican woman entrepreneur building a successful, high-impact agri-food business
Lerato Masuku, a South African construction business builder with a passion for infrastructure development and job creation
Lerato Masuku, a South African construction business builder with a passion for infrastructure development and job creation
Olamide Alade, a Nigerian fashion brand builder with a passion for weaving cultural heritage into every garment
Olamide Alade, a Nigerian fashion brand builder with a passion for weaving cultural heritage into every garment
Mirza Jamal, a Mozambican marcomms expert empowering businesses and brands
Mirza Jamal, a Mozambican marcomms expert empowering businesses and brands
Lovable Dladla, a South African entrepreneur turning a passion for baking into a growing business
Lovable Dladla, a South African entrepreneur turning a passion for baking into a growing business

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